The Flight

We took a direct flight from San Francisco to Rome. If you can avoid a layover, DO IT. I am not sure there is data to back this up, but it seems like air travel in this day and age is usually delayed. I cannot think of anything worse than sitting through a delay with a real life energizer bunny to miss a layover! We experienced a three hour delay but didn’t sweat it because we were flying straight to Rome. If you have control over it, I also suggest an evening flight. It was approximately 12 hours of flying time from SFO to FCO, but Emilio slept for 4-5 hours. He has never slept on an airplane, but with the help of some Benadryl (I consulted my pediatrician on this before we left) he eventually fell asleep once he realized it was past his bedtime and his crib was no where in sight! This REALLY helped break up the monotony of being in the air. The last three hours of the flight felt the longest. Emilio has no interest in watching shows unless it is a music video on YouTube. Streaming doesn’t work 32,000+ feet in the air and he gets frustrated with screen grabs because he cannot tap and swipe to navigate a recording. Stickers (get the biggest pack you can find), window clings, and Trader Joe’s freeze dried blueberries SAVED me the last few hours. I made room in my carry-on bag for books, a coloring book and crayons, multicolored pipe cleaners, painters tape, and Play-Doh. Maybe those items would entertain your child, but they did not do it for Emilio. Before I conclude this portion of the article, I need to make it abundantly clear how invaluable the Baby Zen Yo-Yo stroller is. It folds so compactly that you can fit it in the overhead compartment, or underneath the seat in front of you on the airplane. Better yet, you can roll your little one right onto the plane and fold it in the aisle when you get to your seat! I am not sure of the dimensions on competing strollers that are marketed for travel, but I have never seen this done with another brand. 

When in Rome

We had a car service to pick us up from Rome–Fiumicino International Airport and drive us to the hotel we were staying in for the night. The same driver would drive us to the train station the next morning. I knew we would be falling over with luggage as it is that I made the decision to leave our carseat (and the giant backpack that accompanies it) at home. We requested that the car come equipped with a rear-facing car seat. This was definitely the right decision but I cannot stress the importance of double checking and re-confirming that the car will arrive with a car seat installed. Trust me, you cannot ask enough times. We stayed at the Hotel d’Inghilterra when we arrived and when we departed Rome. We REALLY like the location. It was not close enough to walk to from the train station (which is why we booked the same driver the following morning to transport us to the train station), but it sure was fun to explore the “neighborhood” and bop around the cafes and restaurants. Where there is cacio e pepe, there are the Kaplans. Being a Roman dish, it was only fitting to go out for a bowl or two. We enjoyed Dilla Ristorante for pasta on our way in. It is a quintessential Italian eateery with cute outdoor seating area and gourmet homemade pastas. On our way out, we dined at Antica Birreria Viennese. The beautiful floral facade totally drew us in. The food was not quite as “gourmet,” but the menu was more diverse and included pizza…Emilio’s request! My favorite meal in Rome, however, was breakfast at D’ Angelo! They served delicious egg dishes, coffees, pastries, and best of all Maritozzi. OMG. You cannot visit Rome without indulging in this delectable pastry. It is not heavy even though it sounds like it. It’s a light and airy sweet bread filled with cream. Literal heaven in your mouth. Now regarding the stroller and the cobblestone streets – totally doable. Emilio is a city boy and used to walking so it wasn’t necessary for our time spent in Rome, but we did notice multiple other families with Yo-Yos maneuvering just fine. 

Getting to the Amalfi Coast

Our first stop on the itinerary was the town of Amalfi. Technically you can drive, but there are so many high speed train options out of Rome. The train ride is about 1 hour and 10 minutes compared to a four hour drive. Traveling by train also allows you to avoid the whole car seat issue. We booked a direct train to Salerno (the closest station to our destination) but unfortunately a fire was obstructing the road from Salerno to Amalfi. We diverted to Naples at the last minute. There are two rail lines you can choose from and three ticket classes to choose from. If you are not ready to commit to a departure time in advance, you just take what you can get class-wise when you finally buy a ticket. We bought tickets less than 24 hours before on our way to and from the coast. I was not about to test Emilio’s patience (especially after a 12 hour flight and nine hour time change). The “Club” level was all that was left for both trips. This is the most “boujee” of the three classes. They were about 325 euros total, about $110 per person, and included complimentary alcoholic and non-alcoholic beverages, and food. The Freeciarossa line was more luxurious of the two but they are both adequate especially for such a short ride. I arranged via the concierge at our hotel for a driver to pick us up from the train station in Naples and chauffeur us to the resort. It was a 1.5 hour windy and twisty albeit a beautiful ride. If you are prone to car sickness like I am, take non-drowsy dramamine! Yikes. I am so thankful Emilio did not inherit this trait from me! 

Hotel in Amalfi

I knew the first leg of the trip would be the most exhausting. I wanted us to be able to veg out and re-charge our batteries. A resort with all of the amenities was most suitable to do so. After much research I debated between Hotel Santa Caterina and Anantara. I chose the latter because by the looks of it, it just seemed more kid-friendly. Anantara was closer to Amalfi center, and the cutest little waterside playground! This one-of-a-kind property is built into the cliffside of an ancient convent. There are only 52 rooms, giving it a “boutique-y” feel with all the bells and whistles of a luxury resort. There is an impressive outdoor gym with panoramic coastal view, a lovely spa, several dining options, and a GORGEOUS infinity pool with breathtaking view. We really enjoyed spending the day at the pool and then strolling down to Amalfi center. Due to the cliffside architecture, you must go down some stairs to reach sea level and the center of town when on foot. Alternatively, Anantara offers a shuttle on demand and makes it really easy to get to and fro. Really there was not one thing I didn’t like about this hotel. I still miss our breakfasts with Marcelo and the delish omelets that were conveniently included in the room rate! The room was very elegant, and best of all, the AC was powerful (I cannot say the same about the AC in Rome or Positano). I would absolutely stay at Anantara again.

Where to eat in Amalfi 

La Locanda Della Canonica at Anantara was the best pizza I ate in Amalfi. The tables line the “Walk of the Monks” on a beautiful terrace overlooking the Mediterranean Sea.

Taverna Buonvicino a hidden gem in the middle of town near the main cathedral – you will need Google Maps to navigate here. The cute courtyard and its twinkling lights is just SO inviting. You will not find pizza here, though the fried bruschetta could satisfy a craving for some ‘za. We ended up eating dinner here twice because the ambiance was so special. I must note, this is not the place to go if you are short on time.

Lo Smeraldino is not fancy, but it is right on the water, near the playground, and it opens at 6:30 – a little earlier than most restaurants nearby! This is a great option if your little one is craving a pizza. We ate dinner here, then hit the playground before finishing off the night with dessert from Savoia.

Savoia is your one stop shop for gelato or sweet treats. I went daily for the simplest, yet most delicious thing. A butter cookie with Nutella filling. Decadent. Jonathan was infatuated with what looked like a croissant muffin drenched in RUM.

What to do in Amalfi

Besides pool time and eating and indulging, you can easily catch a ferry to Positano, Sorrento, or Capri for the day. Since we were continuing on to Positano and Capri for extended stays, we went to Ravello for half a day instead. This town sits higher up the coast from Amalfi and is reachable by car – about a 30 minute drive. Just as you would imagine, the views are awesome. There are no cars allowed in the town, so you will be dropped off and then proceed by foot. You can definitely bring a stroller with you, but remember to take the path to the right when it forks. Otherwise you will be stuck with a bunch of stairs. We steered to the left and schlepped the stroller up several flights of stairs to Villa Cimbrone! Funny now, not so funny then! There we toured the lush gardens and enjoyed a snack at the cafe. If you stay till closing, eat dinner closeby on the terrace at Hotel Villa Maria. This spot was very kid friendly and even had a changing table in the bathroom!

Getting to Positano

The hotel concierge in Positano scheduled a transfer from Anantara to the hotel with this company. I highly recommend utilizing the concierge wherever you stay to assist you with booking of car services. It was an easy but twisty drive! We were in the car for 45-ish minutes. The time passed quickly because our driver Mario was kind enough to play Pepas the entire time! If you do not arrange for a private car, you can get there by taxi or ferry. We always choose the path of least resistance when Emilio is with us, and one major benefit of a private car is that they can pick you up right outside the hotel lobby.

Hotel in Positano 

Due to the cliff-like nature of Positano, many hotels are for adults only. I found Hotel Marincanto through a mommy blogger and I am very happy I did! Like I said earlier, we had a stay planned to the famous Le Sirenuse before Emilio was born in 2020. Sadly they do not allow children under five, so that re-booking had to wait. Marincanto is SO close by – only a couple of restaurants separate the two hotels, and the property is kid friendly. Hooray! I booked a standard room with a sea view and terrace knowing we’d only be there for the weekend, but long story short, we were going to have to switch rooms mid-stay so they upgraded us to a suite FREE OF CHARGE to avoid us having to switch. Now THAT is service. There are not enough words to describe how massive the Prestige Suite was. The terrace was enormous. The hot tub overlooking the water in the sprawling bathroom was ridiculous (for lack of a better word). The dressing room…I legit want it for my own home. If you did not see the room tour on my IG story, do yourself a favor and check it out on my Italy story highlights. The other thing that attracted me to Marincanto was that it is the only hotel with direct beach access. I knew we would not be spending time in the sea in Amalfi so getting into the water in Positano was a top priority! Now direct beach access in Positano comes with a lot of stairs…and I mean A LOT. Being from San Francisco and regularly climbing ginormous vertical hills, it takes a lot for me to remark about the steepness of something. This descend and ascend was HELLA steep. Don’t forget your water shoes or sunscreen in the room! But the reward is worth the effort in my opinion. I cannot even describe how invigorating the sea felt on a hot summer day. The room rate included a breakfast buffet with all the essentials, as well as made-to-order egg dishes. Marincanto checked all the boxes for us.

Insider tip: From my experience, room inventory in Italy is not always updated in real-time. It is always worth emailing the hotel of interest and and inquiring about a stay before “giving up” hope!

Where to Eat in Positano 

L’Incanto is where it’s at if you are hanging out at the beach. OH EM GEE we REALLY enjoyed the food here. The menu was extensive with appetizers, salads, pizzas and pastas, cocktails, and fresh fruit. We dined here two consecutive days for lunch. Our friends told us to order “Nerano” pasta as much as possible on the Amalfi Coast. This dish is actually named after the small Amalfi town where it originated. It is spaghetti in a light but creamy provolone sauce topped with fried zucchini. It was lip-smacking good and we were happy to see it on the menu at L’Incanto. Emilio loved the pizzas and the fruit platters were so refreshing after being in the sun. 

If you are looking for dinner with a view, Ristorante da Costantino IS the spot. This family run restaurant sits at the top of Positano – request a window seat. Have your hotel help you coordinate a complimentary shuttle to and from the restaurant. You gotta try the cheese crespelles and let me know how they are. Somehow I did not do my research ahead of time to know they were a must-have item! I was dying for meat and opted for a steak. It was was served in an oil and garlic sauce that was so tasteful. I absolutely dipped bread to finish the remaining sauce. Licking your plate is not socially acceptable, but if it was…

Angelo Pasticceria is a great spot to grab and go, or enjoy a quick coffee. This standing-only cafe is diagonally across from Marincanto and we hit it up a handful of times. I appreciated the smoothie assortment, and Emilio loved the juice menu. It was this very spot where Jonathan and I ate our favorite sandwich on the trip – we picked the wrong day to share! It was a simple caprese sandwich on fluffy focaccia bread, but boy was it GOOD! 

Hotel in Capri

I absolutely adore Capri. It is a magical place. I could stay there forever. It was a small town feel, the people were friendly, it was chic, and the shopping was phenomenal. The store owners were greeting Emilio on a first name basis by day three. But I am certainly NOT the only person who feels this way! We met several people who have been visiting the Island annually for 20+ years. SEVERAL repeat travelers. With that said, book your hotel as far out as possible so that you are guaranteed the accommodations of your choice. We are SO spoiled that our very special friends from SF are from the Island. They gave us so many insider tips that guaranteed an unforgettable vacation, including where to stay. There are a few larger scale hotels on the outskirts of the island. But if you are like me and thrive in a metropolitan atmosphere, I recommend staying in the heart of it is all! Our friends recommended: Hotel Minerva, Hotel Mamela, Hotel Villa Brunella…if you look on a map, all of these hotels are centrally located and nearby each other. This trip was not planned far enough in advance so my first choice, Hotel Minerva, was already booked. I looked for other options in the same vicinity and came across Casa Morgano. I ultimately chose them over Mamela because the room had a bathtub. When you are traveling with a young child, these “minor details” become not so minor! I knew we would be spending the least amount of time in our room in Capri, so as long as the hotel was in the proper “zone,” had a sea view and a bathtub, I was happy. Casa Morgano checked all the boxes! The personnel was so kind, and we loved the location. It sits on Via Tragara – a beautiful street with immaculate villas and a gorgeous terrace with sweeping view.

Insider tip: From my experience, room inventory in Italy is not always updated in real-time. It is always worth emailing the hotel of interest and and inquiring about a stay before “giving up” hope!

Where to Eat in Capri 

Breakfast and Libations

Our room rate included a breakfast buffet but we were eager to do as the locals do! We ended up dining at Il Piccolo every morning. I genuinely miss it! We befriend the servers and they knew what to order upon our arrival. It felt so much like the neighborhood coffee shops we frequent in SF. Emilio eats a very balanced diet at home but he was on a carb-full meal plan in Italy! He LOVED a Nutella croissants and steamed milk for breakfast. We enjoyed the omelets and caprese sandwiches as well. But what I really looked forward to each morning was an iced cappuccino. I do not know how they do it. It tasted like chocolate. I asked several employees and it was made abundantly clear that there is not a “secret chocolate ingredient” mixed into their espresso. It just tastes THAT good. OH MY GOSH. Coffee in the states simply does not compare to the cappuccino in Capri. This little cafe is perfectly situated in the square – a great place to people watch and it is open all day. If breakfast is not your thing, hit it up in the evening for a cocktail while the sun sets. 

Gelato and/or other savory/sweet treats

Buonocore has established quite a reputation. The smell of freshly made waffle cones alone will lead you here. Brace yourself for the line at the gelato window…or wait till the last ferry departs and the streets clear of day trippers. But not only is the gelato divine, they offer a large assortment of pastries and savory snacks (pizza squares and sandwiches as well). We enjoyed the gelato of course, but on our last day on the island, Jonathan tried a cannoli and could not believe his tastebuds LOL.

Insider tip: skip the gelato line all together and walk inside for other savory and sweet treats.

Drinks

I already mentioned Il Piccolo, but it is a very special cafe in the square that transforms into a bar in the evening. If you are looking for something more unique, Capri Rooftop at Hotel Luna is spectacular. The view is sweeping. I couldn’t believe my eyes quite frankly. We got in without a reservation and were seated further from the view, but they allowed kids and we still had a great time. The Catwalk drink is SO refreshing and delicious. My suggestion would be to make a reservation so that you are guaranteed a table with a view, and enjoy a cocktail and snack before your dinner reservation. Another rooftop option but with a city view is that of Hotel La Palma. A hip atmosphere, catchy music, and great assortment of cocktails. If you follow me on Instagram, this is where I wore my new Pucci outfit – the same print Beyonce is wearing on tour!

Dinner

There are so many delicious restaurants in Capri. I wish we had more time to try them all. As most of Italy, many close after lunch service around 3:00 pm and then reopen at 7. Just throw your toddler’s schedule out the window! I will list all of our friend’s recommendations later, but we went to the following:

Villa Verde is where all the celebrities flock to who visit the island. There is quite an impressive photo montage on display of the celebs who frequent this spot. It is a garden atmosphere in the heart of Capri, where you will find all the pasta and pizza your heart desires. Everyone seems to genuinely enjoy working at this restaurant and Franco, the owner, is so hospitable. If you are a fan of truffle, the tartufo pasta is insane, and if you are a meat lover, the bolognese is the best I have ever had. But don’t let me get ahead of myself. You cannot dine at Villa Verde without trying the Buffalo mozzarella. 

Panorama just like its name alludes to, boasts a sweeping view and a great offering of pastas and pizzas. If you make a reservation ahead of time, you can request a table on the terrace. The fungi and Margherita pizzas were our favorite here. The vibe was pretty casual and the personnel was over-the-top friendly with Emilio! This was his favorite dining experience in Capri.

Insider tip: Add a ball of burrata to your pizza – you will not be disappointed. 

Da Paolino is a very unique experience reachable via taxi. Wine and dine under a lemon grove at this special Capri eatery! Try the mozzarella appetizer grilled in between lemon verbena leaves. We were there with another family and all shared plates and a lot of wine. Definitely save room for the dessert room! Yes, you read that right, a “temptation” room full of miniature desserts that you can fill your plate with!

Insider tip: request a reservation on the website here – you will need your passport handy. 

Bianca…this place really impressed us. We asked Antonella at the Pucci store where we should go dressed to the nines, and she suggested Bianca. After 10 days of pizza and pasta, we were pleasantly surprised by the meat and fish-heavy mediterranean menu! All of our meals were memorable in Capri for different reasons but this was our most memorable meal for food. Everything we ordered was SO good. We started with a burrata appetizer, but for my entree, I ordered a roast chicken and deep fried eggplant dish that came with a side of tzatziki. If this was available in SF, I would order it weekly. Jonathan tried the catch of the day which included hummus and pesto- two Kaplan favorites. He devoured it. We also tried a rice and chicken and fish side that was tasty too. The portions were not huge – you could easily share the plates family-style. Emilio was totally content with his “Not a pizza” Margherita pizza. The dough does not rise – it is cracker thin, but it will still satisfy a pizza craving.

Other highly recommended restaurants include: Le Grotelle, Aurora, Zagara (Anacapri), Il Riccio

What to do in Capri 

Like I said before, I knew we would be spending the least amount of time in the hotel room in Capri because there is so much to do and see! I am going to go in depth regarding the activities we participated in, but I’ll list more from our friends’ recommendations afterwards. The shopping is a given in Capri. The impeccably clean (and stroller friendly streets) are lined with some of the world’s most luxurious boutiques as well as local artists and retailers. I was immediately sucked into the children’s store Russo because I wanted to buy Emilio an Emilio Pucci item. Can you blame me?! After that, I found myself in the women’s Pucci store but THAT experience deserves a blog post of its own. Stay tuned! 

The shopping is great, and the restaurant and cafe hopping is fun, but if you have your mind set on taking a dip into the perfectly blue Mediterranean Sea, then you need to visit a beach club. Now these beaches are not your typical Floridian sandy beaches. They are rocky (do not forget your water shoes), but SO refreshing, all-inclusive, and actual paradise. We had such an incredible day at Lido del Faro (the lighthouse). I cannot recommend it enough. It is about 20 minutes by cab from Capri square, but well worth the travel time. You will walk down a winding path from the cab stand, but don’t fret – paradise awaits and it is stroller friendly. There you will have access to beach chairs, a saltwater pool, changing rooms and bathrooms, and a delightful waterfront restaurant. There is waiter/waitress service with many adult beverages, and virgin libations alike, flotation devices for lend, and they will help you call a cab upon your departure. Remember, this is not a sandy beach. You will reach the water via stairs. You will be treading water. I brought an infant life vest for Emilio and borrowed a “noodle.” It was an experience of a lifetime to immerse as a family in that heavenly sea. A reservation ahead of time is safest, but if you forget, have your hotel concierge call the morning of.

Insider Tip: the sun stays out all day on this side of the island. Plan to stay at Lido Del Faro till sunset. 

Other notable beach clubs include: La Fontelina, Marina Piccola (if you have kids you can wade into the water here), Marina Grande (another option if you have children since you can wade in), Gelsomina a lovely pool popular for adults and children alike. Contact your hotel concierge for transportation options. 

Fold the stroller and visit Anacapri by bus or taxi for a quaint little day trip. This town is just 10 minutes up the hill from Capri square, and has a plethora of stores and restaurants to tempt you. It is a little more low key than the town of Capri itself. Aside from a pleasant stroll, you can take a chairlift (just like a ski lift) to Monte Solaro at the top of the island. Here you can admire the view and jaunt down the Pizzulungo walk. Emilio was overtired and stubborn when we went to Anacapri (this only occurred once on our two week long trip) so we didn’t push it and ride the chairlift. But we did enjoy a light lunch at Il Solitario. Another notable restaurant in Anacapri is Zagara, and it is located across from a playground! Make sure you check the park hours – it was closed around lunch time. 

Rent a boat or visit the Blue Grotto. The water was choppy when we were on the Island. There was rain in the forecast a couple of days before our arrival. We did not get to tour the island by boat, although we felt totally satisfied with what we saw on land! Your hotel concierge can help arrange this for you. Some beach clubs and restaurants are more easily accessible via boat so it is worth looking into. We were disappointed that due to thee water level the Blue Grotto was inaccessible. This I hear is quite the unique experience. You legit paddle into a cave on a tiny boat. Think twice if you suffer from claustrophobia. I hear the water is incredible to swim in inside the grotto. Our friends advised us to go late – after 5 pm once the ferry traffic clears. This way you can experience it without the crowds. We will definitely make this a priority on our next trip…because there will be another trip – I loved it that much!

Closing Remarks:

I am still dreaming about our vacation…it was truly extraordinary. And if you follow my recommendations, you too can experience a trip of a lifetime! Just remember, when you travel to a country that is not your own, take a deep breathe and trust the process. There were a few times especially with our luggage where we thought, “well this would be handled way differently in America…” but everything ended up working out. If you are traveling with a toddler, remember they are resilient. They will adjust when they get home if bedtime is 3 hours hours later than normal. If they miss a nap, squeeze in a catnap in the stroller. Every time I think I am ready to publish this article, I remember another detail that could be helpful to a family traveling to the Amalfi Coast. If there is something that I missed and you’re dying to know, just leave me a comment below, and I will gladly make an edit. Safe travels!

The post Vacationing in the Amalfi Coast with a Toddler appeared first on Kelsey Kaplan Fashion.

What to Do

Take in beautiful coastal views along the Road to Hana. Although the Gypsy Guide app makes it possible to drive without a guide, add Sandy Cheeks Tours to your phone STAT! Kyle will customize your tour to meet your road trip needs and desires. Not to mention he stocks the car with snacks and cold beverages.

The Haleakalā National Park sunrise tour and bike ride is impressive and worth the early wake up call. Consult your hotel concierge for specific guide recommendations.

Surfing is apart of the Hawaiian culture and lifestyle. Do as the locals do and take a surf lesson with Aloha Ocean Adventures Ikaika and Keoki run an awesome business and I cannot recommend this “surf school” enough! If Ikaika can get me and Jonathan to tandem surf on the first try, he can get anyone to stand up and ride the waves! Proof is in the pudding.

Whether you’re surfing, snorkeling, or swimming, chances are high you are accompanied by the sea turtles. These creatures are very sizable and it is fascinating to observe them in their natural habitat. Make a sunset trip to Tavares Beach for a turtle showcase!

Where to Eat

Y’all already know I looooove to EAT and there is no shortage of good food in Maui. Monkeypod Kitchen is known for its frothy Mai Tais, and they do NOT disappoint. The setting is electric and the menu is fairly diverse. I’m not a big fish eater (I never acquired the taste) but I was pleasantly surprised to find delicious fish-free food offerings. I mean Hawaii is the place to eat fresh fish! Believe it or not, the ramen noodles were divine. Full service is available at the bar, but make a reservation to spare yourself the hassle.

Mateo’s Osteria is home to delicious Italian cuisine. Sometimes there’s nothing more satisfying than a big bowl of pasta or PIZZA. Did the pizza life chose you? I’m definitely one of the chosen ones! Anyway, we snacked on a flatbread and filled up on pasta.

Longhi’s is located in the outdoor mall and has a little something for everyone. I suggest lunching here during your shopping charades. Consider a Greek salad if you’re a light mid-day eater.

Ka’Ana Kitchen was our favorite meal by a long shot…and it’s on-site at the Andaz! Whoa, whoa, WHOA!!!! This farm to table concept restaurant takes all of your favorite flavors and concocts then into mouthwatering dishes. I’m talking watermelon “steak” drizzled in balsamic vinegar topped with creamy feta and Hawaiian sea salt. OH EM GEE. I could have lived off of this stuff. Fried chicken…who doesn’t love fried chicken?! Yeah no one…well, the master chefs served up chicken and waffles on a decadent syrup infused pancake instead and topped it with jalapeño sauce. Never mind the lemon butter cream sauce…drooling. We went back for seconds. But if red meat suits your fancy, indulge in the skirt steak (pictured here) and wash it down with a “creamy” moscow mule. The cocktails are inventive too – who knew coconut cream would be the perfect addition to a traditional moscow mule?!

P.S. Locals and tourists alike rave about Mama’s Fish House. Lesson learned: BOOK A RESERVATION SEVERAL DAYS IN ADVANCE!

Where to stay

This was our second trip to Maui, and specifically to the Wailea Area. We enjoyed our stay the first time around, but we really appreciated how easy everything was at Andaz. To name a few…the car service, 24 hour market, on-site Enterprise Rent-A-Car, and abundance of pools. Whether you’re going out to eat or hitting up the shops at Wailea, the complimentary car service will shuttle you to and fro in luxurious SUVs. The 24 hour market is simply genius and frankly every hotel property should have one. It was like a pimped out gift shop with all the beach wares, an ice cream stand, fresh pastries, beer and wine, as well as a plethora of hot food items. The breakfast burrito was a hot commodity.

Resort fees are a doozy, but they hurt less at Andaz. High speed wifi, paddle board rentals, guided canoe tours, snorkel equipment, GoPro rentals, etc.,  are covered. In a nutshell, stuff you actually want to take advantage of!

Now I could go on and on about the lush landscapes, sunsets, and private beach, but pictures speak louder than words! Mahalo for reading.

Shop my resort wear:

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Eating and Dancing in Vegas

Now that you know what to wear, where to stay, and what to see in Las Vegas, let’s talk food and dancing! Conveniently located across the street from the LINQ is Hell’s Kitchen, home to world-famous chef Gordon Ramsay! From specialty cocktails, delectable apps and mains, to a heavenly dessert menu, you cannot go wrong with this restaurant choice. Standout food items include: meatball appetizer, beef wellington, and sticky toffee pudding.

After dinner, cross the street to the Cromwell and burn off some calories on the dance floor at Drai’s Beachclub & Nightclub. This indoor/outdoor nightclub features mostly hip-hop music. Dress to impress and prepare for a late night. Remember, the party doesn’t start till 11 pm in Las Vegas.

This rose gold wrap dress is PERFECT for a night on the strip. Not only would I absolutely freeze in a dress like this in San Francisco, but I would probably get a lot of puzzled looks! Las Vegas and New York Fashion Week have something in common. You can wear whatever the heck you want! I am always confident in my clothes (or I would not wear them) but it was my first time wearing a sheer-overlay dress. What little “anxiety” I had was long gone once I saw about 10 other women in similar styles. Full Disclosure: I had it shortened a couple of inches and I am wearing four inch heels. Aside from that, the built-in bodysuit and criss cross straps are petite girl friendly. Remember this the next time you pack for a trip to Vegas: ANYTHING GOES!

Shop the Post:

Rose Gold Wrap Dress | Sandals (SALE ALERT!) | Earrings | Purse

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Your Colombia Travel Guide to Bogota, Medellín, and Cartagena

Where to stay:
Sofitel Bogota Victoria Regia is located in the heart of “La Zona Rosa,” about 40 minutes from the airport. We had a wonderful three nights at this hotel and highly recommend it. The WiFi was complimentary, the breakfast was included with the room rate, the bed was heavenly, and the location is superb. Jonathan and I like being steps away from the action. City life in San Francisco has definitely rubbed off on us! The Zona Rosa has something for everyone and Sofitel Bogota boasts a beautiful property in the middle of it all.

Where to Eat:
La Puerta Falsa in “La Candelaria” serves up authentic Colombian Cuisine and has been since 1816! This hole in the wall joint lives up to the hype and is worth the wait. Get the chicken soup and chocolate plate to start. Don’t ask…just do it! You won’t regret it.

Casa, just two doors down from Sofitel Bogota, is an open-air restaurant offering international food with a Colombian flair. We sat on the heated back patio and for a minute it felt like we were back home in San Francisco!

Dinner at Casa San Isidro on top of Monserrate is an absolute must. We were afraid it would be an over-rated tourist trap, but were pleasantly surprised by the good eats. Ask for a table by the window and prepare to be amazed.

What to do:
“La Candelaria” offers more than just fine food. Rich in history, the Museo de Oro (Gold Museum), the Museo Botero (a famous Colombian Sculptor), and plentiful street art can be found here. Word of advice, arrange a guided tour.

If you’re in the Candelaria neighborhood, you MUST take the cable car to Monserrate for a panoramic view from (10,000 feet up) of the eight million person city. Twin Peaks has got nothin’ on this. WHOA! And while you’re at it, stop for a bite at Casa San Isidro. Dress warm because it’s cold and windy up there. I’m talkin’ 45-50 degrees chilly.

Tip: Avoid the hassle of exchange rates and use Uber to get around Bogota. WiFi is available throughout the city. Please note you will be more comfortable in an Uber Black versus an Uber X, and the difference in cost is negligible.

What to Wear:
Our summer months are Bogota’s winter months. To me, the temperature is perfect because it is very similar to San Francisco. 50s at night (although it felt warmer than that) and 60’s during the day. I dressed in layers with jeans, wedge sandals, and lightweight denim jackets.

Top | Jeans | Wedges | Purse | Earrings

Jeans (similar) | Sweater | Wedges | Purse

The Spanish in Bogota is very textbook – it is very pure and easy to understand. In fact, I used my Spanish all day everyday while we were there. Jonathan, on the other hand, will vouch for me when I say that it would be challenging to visit Bogota without knowing the language…and four years of high school Spanish is not gonna cut it. That is not to say you cannot go there unless you speak Spanish, rather do some research ahead of time, and hire a bilingual guide.

Medellín

Medellín is an incredibly beautiful city. Here you’ll find desolate country-side as well as bustling nightlife. The city sits in a valley made up of mostly high rise buildings. There is no such thing as a bad view in downtown Medellín!

Where to Stay:
The Charlee Lifestyle Hotel is where it’s at. Located downtown on Calle 9A, this property is simply chic! Featuring a pool/sushi bar on the roof deck, this place is regarded as a Medellín hotspot by locals and tourists alike. Also included in the room rate at Charlee Hotel is WiFi and breakfast – much appreciated. Again, location, location, location. EVERYTHING is steps from the hotel lobby. Boutiques, beer gardens, coffee shops, flower shops, you name it. It felt very much like the Marina District in San Francisco.

What to Eat:
Envy Rooftop on the 17th floor at The Charlee Hotel serves up sushi and Asian Fusion from 5 pm – midnight. And if you’re lucky, it might even be salsa night with live music and entertainment. Regardless, the sushi rolls are works of art and very sizable. Start with the chicken wings and make your way to the salmon and avocado crunchy roll. A “dress to impress” dress code is enforced.

La Guachafita Del LLeras is great for a pre-dinner cocktail or post-dinner dancing. The drinks are all made-to-order and are a good bang for your buck. We enjoyed fresh sangria and pina coloda out of a hollowed out pineapple. You cannot visit an exotic location as a blogger without taking that obligatory fruit beverage photo!

What to Do:
Riding the cable car in Medellín should be at the top of your to-do list. From here you’ll witness sweeping views of the valley and have a better understanding of the typography and challenges it presents. In 2004 the “teleferico” or cable car was constructed as a means of public transportation. This project made it possible for people in the mountainous regions to hold jobs in the big city.

Consider a four hour guided tour. Short and sweet but just enough time to broaden your horizons. Start at Botero Park and finish up over a late lunch at Pueblito Paisa.

What to Wear:
The climate in Medellín is heavenly. There was little to no humidity in the air and the temperature was a consistent 75 degrees. This is very easy dressing weather in my book – anything goes. I rocked two-piece pants sets, a maxi dress, and shorts during the tour.

Top | Shorts | Wedges | Purse

More about the look here, or shop it here:

Dress | Earrings | Wedges | Purse

Medellín is magical. It is very American-friendly as there is city-wide free public WiFi. Uber again works seamlessly from here. The Spanish is slightly faster than Bogota, but more people speak English. Jonathan would be comfortable returning without his personal translator…ME! We stayed for two nights but will make it three on our next Colombian excursion.

Cartagena

Often described as the “Miami of Colombia” this coastal city takes you back to the future – in a good way. The old city sits behind a concrete wall that was constructed back in 1585! It’s a photographer or bloggers’ paradise. The colorful architecture and picturesque backdrops are plentiful. Jonathan’s job as official #InstagramHusband has never been easier.

Where to Stay:
Cartagena is like its own separate country. I didn’t really feel like I was still in Colombia! I highly recommend staying within the old walled city for a one-of-a-kind experience. We stayed at Tcherassi Hotel and Spa. It was very comfortable, and quiet. A totally different experience from Charlee Hotel in Medellin! The beds were lush, and WiFi and breakfast were included with the room rate. Once again we were walking distance to the heart of the city.

What to Eat:
Patacones, patacones, and more patacones! No really though, fried plantains are a menu staple in Cartagena and I was not complaining. Just make sure they’re the green plantains and not the sweet ones.

El Balcon is a flavorful eatery with an abundant menu of Colombian cuisine. Grab a seat along the balcony and people watch as you enjoy 2-for-1 margaritas and a mouthwatering burger. I’ve never appreciated a breeze as much as I did on our first night in the hottest place on earth Cartagena.

Andante Allegro Vivace is a charming Italian bistro in the middle of the walled city. Here you’ll find Italian favorites such as: cacio e pepe and lasagne, alongside Colombian inspired stuffed pastas. What a treat indulging in Italian comfort food after a week straight of meat and vegetables.

What to Do:
It sounds cheesy, but get lost in the walled city! Start early and end late wandering the magical streets of Cartagena.

Visit Castillo San Felipe de Barajas an old fortress for a lesson in history.

Take a group tour or charter a boat and spend the day exploring Las Islas Rosarios. Here you can scuba dive, snorkel, kayak, etc., in one of Colombia’s most impressive national parks. But don’t be surprised by the rustic nature of the Rosario Islands – you will not find luxurious resorts here! Rather this sanctuary is where you’ll find beautiful white sand beaches and some of the freshest seafood on the planet!

What to Wear:
Is nothing acceptable?! Ha! Cartagena is hot and HUMID. If you visit during June or July I can assure you that you will be sweating the entire time. I saved all my rompers and crop tops for Cartagena and it was the best decision I have ever made.

Top | Shorts | Wedges | Earrings

Romper | Wedges | Purse | Earrings

Thank you for reading my Colombia Travel Guide. Feel free to email me with specific questions should you have any!

The post Colombia Travel Guide: Bogota, Medellín, and Cartagena appeared first on Kelsey Kaplan Fashion.

Where to Eat

It is no secret: I LOVE food! I’m not a “foodie,” rather just a girl who enjoys to eat and appreciates good grub. I use Yelp to map out the restaurants around me and highlight the dog-friendly options. I’m that person who doesn’t know what the inside of the restaurant looks like #dogmomlife. But patios…I got you covered!

If you’re into hummus, kabobs, and baklava, Zoolz Mediterranean eatery is for you. We were impressed with the libations and pleasantly surprised to find halloumi cheese on the menu. Aside from the cheese and beverages, the kabobs and moroccan chicken were both incredible. I’d pay for the yogurt dip recipe!

La Magie is a rich way to start the day. By that I mean that you’re in trouble if you have a sweet tooth! This cafe and bakery offers an array of both sweet and savory breakfast items. I ordered the quinoa scramble and could have licked the bowl clean. It was the perfect protein-packed meal for a long day ahead.

Other notable restaurants include: Barrio (try the sangria), McKay Cottage (get the lemon ricotta pancakes), Pine Tavern (river front patio great for an afternoon drink).

What to Do

I used to think a beach vacation was the only way to relax. WRONG! Bend is laid back, peaceful, and very scenic. I’ll always be a city girl but temporarily stepping away from the hustle and bustle is very refreshing. So what is there to do in a “chill” place in the middle of Oregon? Allow me to explain.

If water sports tickle your fancy, you have options. Float, swim, kayak, or paddle board down the Deschutes River. If you prefer land-based sports, you can: bike, walk, jog, or hike. Pilot Butte in an easy two mile hike with panoramic views of Central Oregon. Leashed dogs are welcome.

Other activities include: shopping, beer tasting (Crux marks the spot), and “parking.” I never knew how amusing laying on the grass could be until I found myself at Drake Park two afternoons in a row. The days are long in Bend – it doesn’t get dark until 9:00 pm. Grab a blanket and take in the scenery. Jonathan refers to the park as “ethereal.” It is like the real-life version of an artist rendering!

Where to Stay

Finding a place to stay in downtown Bend was relatively simple. It needed to be dog-friendly and walking distance to the restaurants. I am happy to report that The Wall Street Suites was only a six minute walk to the heart of downtown, and they offered GG a warm welcoming upon our arrival. Other noteworthy amenities include: tempurpedic beds, fire pits, and complimentary bicycle rentals.

Did I miss anything?! Comment below and I’ll be sure to fill you in on everything I experienced in downtown Bend. Overall I give Bend, OR two thumbs up for food, fun, and Fido. Thanks for reading!

The post Where to eat, What to do, and Where to Stay in Downtown Bend, OR appeared first on Kelsey Kaplan Fashion.

Comfort Food

If you’re on a proper Italian holiday, you’ve probably visited more than one Italian city and eaten your fair share of pasta and bread. For a delicious break from the carb overload, head to Harry’s Bar for All-American comfort food. Positioned right across from the river and minutes from Ponte Vecchio, the burger will not disappointment you after a busy day of sightseeing. Bonus: The assortment of wine and spirits is very impressive and the bartender discusses your options table-side. He makes a mean martini.

Gelato

Oh Em Gee! Never have I ever eaten a more delectable frozen dessert than the gelato at La Carraia! The hazelnut flavor literally tasted like spoonfuls of Nutella straight out of the jar – my ULTIMATE guilty pleasure. Whoa! It wasn’t until after I devoured my sugar cone that I noticed they also serve chocolate hazelnut and yogurt and Nutella flavors. Jonathan thoroughly enjoyed pistachio cream while we admired the very spoiled privileged Italian pups scarf down some vanilla. No joke! Other notable flavors include: Salted Peanut Butter, Mango, Chocolate Chip, and Cottage Cheese and Pear. Take me back!

Cafe

Minutes from the St. Regis sits the very charming Caffe 900 Firenze. This little spot is as sweet as it gets for a mid day snack or treat. Enjoy fresh paninis, pasta salads, or tasty pastries over a hot beverage. I enjoyed a hot caprese sandwich while Jonathan munched on some salmon pasta. Catch up on emails while you dine in style thanks to the free wifi. Now how can I get these tables and chairs to my house in San Francisco?!

Steak

Firenze is known for its “Bistecca alla Fiorentina,” aka a T-bone steak, served off the bone. L’Osteria di Giovanni is where it’s at for a mouthwatering piece of meat. Aside from getting your protein fix here, other popular items include pear stuffed pasta and coccolis – a personal favorite. If you’ve ever tried a beignet from Cafe Du Monde, this is the Italian version. Instead of a fried dough pocket topped with powdered sugar, they’re sprinkled in garlic salt. Tip: Medium rare is the Italian standard – if you do not care for undercooked meat, request medium even though they will try to convince you otherwise.

Pasta

In yesterday’s post, I mentioned the charming trattoria, Pandemonio. GET THE TRUFFLE PASTA! We didn’t stop talking about it for days. The tagliatelle was cooked to perfection and the sauce was just the right amount of rich and creamy. We were very gracious for the shaved white truffle on top – we weren’t expecting that! Aside from the “primi” dish, the house wine was spectacular – we went through a bottle faster than we finished our meal. Note: Florence bakers omit salt when preparing their bread. If you’re wondering why it tastes like leavened matzoh, that’s why!

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Brunch at Bouchon

Does French food suit your fancy?! If so, reserve a table early at Bouchon and prepare to be wowed. Go for brunch and order from the brunch or dinner menu. If you’re in the mood for breakfast food, get the chicken and waffles. I guarantee it’ll be the most succulent chicken you’ll ever eat. Otherwise, the steak frites will not disappoint. Don’t be shy, keep asking for more baguettes and butter…you know you want to!

Cocktails at Bardessono

Lucy Restaurant and Bar at Bardessono is where it’s at! It is here where, patrons gather for happy hour before shuffling off to their dinner plans. The wine and cocktail list is extensive, and the “Nibbles and Bites” menu will tide you over before your reservation. If you dig fried food, order the beer battered onion rings and curl up next to a fire pit to enjoy.

Dinner at Redd

Reserve at Redd for a chic night on the town. This hip space is great for date night or groups alike. After you get your drink on, indulge in the crispy chicken thigh appetizer – your tastebuds will thank you later. The steak on top of potato purée and fried shallots is a great option for a hearty appetite. For a more laid back scene, cross the street for pizza at Redd Wood.

Sweet Treats from Bouchon Bakery

Satisfy your sweet tooth with freshly baked goods from Bouchon Bakery. Chocolate almond croissants, donuts, macarons, and caramel popcorn are just a handful of the many concoctions served up here. Wake up early or leave room for an afternoon pick-me-up to avoid the line. On a nice day, enjoy your pastries in the charming courtyard.

Which establishments do you consider your top Yountville restaurants?! I’d love to hear ’em.

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The beach at Wailea is sheer bliss. The golden sand is as soft as it comes, the water is crystal clear, and the temperature is just right. We rented stand-up paddle boards one morning and enjoyed riding the current along the coastline. On a calm day admire the coral and fish from above, and if you’re lucky, a sea turtle or two may even grace you with their presence. Although I am totally fascinated with underwater life, going down there is another story! I left the scuba diving to my hubby and Makena Coast Dive Charters took great care of him.

Coming from the mouth of a “city foodie,” you will not be disappointed with the cuisine in Maui. We thoroughly enjoyed dinner at Pita Paradise – getting our mediterranean fix in the first night we were there. If you have a sweet tooth, do not leave the premises without trying the baklava ice cream cake. For a casual dinner (see attire here) accompanied by live music and stiff drinks, MoneyPod Kitchen is where it’s at! The bartenders take the ever popular Hawaiian cocktail, Mai Tai, to a whole new level and my photo below does not do it justice. All I have to say is that I was in passion fruit heaven. Aside from the cocktails, notable items include the pumpkin ravioli and the chicken wings off of the appetizers menu. Both lip-smacking good. For a fancy steak dinner (see attire here), you cannot go wrong with Duo at the Four Seasons. After indulging in meat and potatoes, cleanse your pallet with complimentary cotton candy. How about them apples?!

Witness nature at its finest with a sunrise bike tour at Haleakala. Twist your way up to approximately 10,000 feet above sea level to admire the sunrise, then coast your way down the Hawaiian country side on bikes. Do not let your bike riding competence deter you. As long as you can balance on a bike, gravity does the work for you, and there is no better way to experience the unique Maui landscape. Although the 3:00 am wakeup may come as a shock, it is the only way you’ll reach the vista point to witness the sunrise. There is nothing more that I enjoy than a full eight hours of sleep, so believe me when I say, it is worth seeing at least once. Remember to dress in layers as the temperature ranges from 20-40 degrees at the top of Haleakala.

Mahalo for reading!

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