We started our Italian adventure on the beautiful island of Capri checking into the stunning JK Place Capri. We spent the day checking out the hotel and grounds. The boutique style hotel is set on the cliffs with only 22 luxurious rooms, featuring a stunning pool with panoramic views of the Mediterranean Sea.
The first night we walked into the town center and dined at Villa Verde. We sat in the elegant indoor/outdoor dining room and ordered a few of their staples, ravioli, fish, and pizza. The fun part of this restaurante located in the heart of Capri, is that it turns into a late-night club...we were too tired the first night but ventured over later in the week.
The next day we hiked down to the iconic La Fontelina for lunch. We had day bed reservations, but the weather wasn’t really good enough for a day of lounging. Of course, we were still able to enjoy the fresh seafood and Aperol Spritz’s on the seaside balcony.
Terrazza Brunella was our choice for dinner that night. When we walked into the restaurant, located on a terrace right on the cliffs edge overlooking the sea, we were immediately mesmerized by the enchanting pink and oranges of the sunset, offering the setting the perfect mood for the evening. We naturally had to close the night at this restaurant with out of this world espresso martinis.
The next day we thought we had died and gone to heaven. We ventured off the island and went to Conca del Sogno for lunch on the Amalfi Coast. This is a must if you are planning a full day boat excursion. A small dingy picked us up from our boat. Crystal clear waters welcomed us to a dreamy setting and dreamy lunch. After a long leisurely lunch of lobster pasta, wine, and limoncello we made our way back to our boat where we enjoyed the rest of the afternoon swimming and relaxing in the beautiful coves.
For dinner we trekked up to Da Gelsomina in Anacapri where we discovered the beautiful wonder of the other side of the island. The special restaurant, which has been family owned and operated for decades, grows their own fruits and vegetables and cooks with them the day of picking which gives every dish the most exquisite fresh taste. They also produce their own wine and bottle it on the day of use. The mixture of their home-grown produce, fresh fish, homemade pastas did not disappoint.
The next morning, we woke up and hiked the “1000 steps” known as the Phoenician Steps. We started at our hotel and made our way back up to the quaint town of Anacapri. We were able to take in the beauty of Capri from many different angles and perspectives. After a beautiful morning checking out all the darling shops we jumped into a fun blue convertible taxi and headed down to Il Riccio. We felt like we were in a movie with the salt air in our hair and Italian music blasting from the radio. We were blown away by this amazing restaurant. Being early for our reservation we took a detour to their bar to treated ourselves to their Spritzs…. but we were blown away to discover their bar was a glamorous Christian Dior popup on a beautiful seaside terrace. We then headed down to the most unbelievable restaurant. Il Riccio is simple but sophisticated and decorated with beautiful blue hues to compliment nature's scenery. With incredible service from super fun staff, we dined on the catch of the day cooked in a salt crust and served with the most delicious potatoes, tomatoes and zucchini. There was a little surprise at the end when we were escorted to the temptation room which was overflowing with a rich selection of sweets from the Neapolitan pastry tradition.
For our last night in Capri, we headed to the center of town where we dined at Aurora, which is the oldest restaurant on the island. The setting was so beautiful, and we were surrounded with the best people watching and scenery. The restaurant was so fun and upbeat, and we dined on their famous pizza and local seafood.
Our family continued our journey checking in to the iconic Il San Pietro di Positano. We were obsessed with its old-world vibe and understated luxury. Trust me when I say, you will not want to leave. We tried to spend as much time as possible at the hotel. We dined at the pool restaurant for lunch and enjoyed their Michelin restaurant, Zass, for dinner. Don’t even get me started on the cocktails and wine.... they were over the top amazing and we enjoyed them while listening to live music. We played tennis on their world-famous tennis court where we discovered that the view is even better in person. Following this We sat at the beach club and had a few workouts in their beautiful gym which is surrounded by lemon trees. I am so in love with everything about this hotel. The beauty is remarkable.... elevators carved into the cliff, lavishly decorated guest rooms, no details were spared.
One of our nights in Positano we opted for a casual restaurant with a local flare. We got really lucky when we were able to score a table at Mele Pizza and Grill. The owner picked out our entire meal for us including our wine. It was truly one of the best meals I have ever had. The food was over the top delicious...pizza, meatballs, gnocchi, local wine, etc. We were so lucky to enjoy this authentic night on the beautiful side streets of Positano.
After a beautiful little road trip from the south, we arrived at our last stop in Rome. We checked into the very beautiful Hotel de la Ville which has an amazing location right by the Spanish Steps. We even had some fun celeb sightings while we were there. We have done a lot of touristy activities in Rome over the years, so on this visit we were on a mission to check out some vintage shops. My favorite lunch spot in Rome is Buvette. We have eaten here several times and it’s the perfect place for a pit stop when you need a break from shopping and exploring.
For dinner we tried Alfredos. I had to visit even though it has become a bit touristy because my dad was an alfredo connoisseur, he never made it here, so we went for him. The alfredo was made fresh right at our table and definitely gave our taste buds a party.
The last night we ate at the most incredible place, Taverna Trilussa Trastevere. Our taxi dropped us off at the ivy-covered entrance in the very charming Trastevere neighborhood. I immediately knew we had made the right choice. It’s a local landmark serving up Roman staples. Their special ravioli is one of the best things I have ever eaten. The ambiance and vibe were so incredible we did not want to leave so we remained for hours soaking up the ambiance and wine. Our love for this restaurant did not stop there. Little did we know the restaurant had a tennis theme. The owner is friends with Roger Federer, and it’s become a hot spot for players when they are in town for the Italian open. It just so happens we were there the day after the Rome finals and had an iconic tennis sighting while we were there.
This was an incredible family vacation for us, providing us with unforgettable memories. Having two girls in college I’m not sure how many more big vacations with our family of four we will have in our future so we will hold onto this experience forever. I’m going to link a few of our favorite spots below as well as my beautiful friend Lou Delisser who helped plan our trip.
And of course we needed to pack our Italy must-have styles! For tennis, pack our Hadley Dress in bright baby pink for a touch of elegance on the court. When exploring, opt for the Jean Dress, ensuring comfort without compromising style. Indulge in a shopping spree with our original Hadley Dress for the perfect blend of sophistication and flair. Set sail in style with the Kristin Dress, our (currently) unreleased, perfect length lounging dress, ideal for relaxation. Lastly, top off any style with our Bespoke Court Hoodie offering both comfort and charm everywhere. With these Italy style essentials, you'll be ready to embrace any occasion with these timeless pieces that embody elegance and functionality.
Hotels: JK Place Capri, Il San Pietro Positano, and Hotel de la Ville.
Italy Packing List Essentials: Hadley Dress (baby pink), Jean Dress, Hadley Dress (kelly green trim), Bespoke Court Hoodie, and the unreleased Kristin Dress.
Restaurants: Villa Verde, La Fontelina, Terrazza Brunella, Conca del Sogno, Il Riccio, Da Gelsomina, Aurora Capri, Mele Pizza and Grill, Zass Il San Pietro, Carlino Il San Pietro, Alfredo alla Scrofa, Traverna Trilussa, and Buvette.
Shops: Da Costanzo Capri, Delfina, Laboratorio Capri, Eres, Carthusia, Theodora, Luisa Positano, Positano Courture by Blitz, Macrame Temptation Positano, Mercantile, Delfina Delettrez, Suite Benedict, and Gucci (obviously).