For my upcoming 40th birthday I wanted to celebrate another year around the sun by gifting my family a vacation. I knew I wanted to go to the Amalfi Coast and Greek Islands because they have always been at the top of my travel bucket list. My daughters are 14 and 12, a great age to experience (and hopefully remember) Europe for the first time. The best part about the entire experience was how appreciative they were and how close we became as family following this trip. It was truly magical, a dream come true, trip of a lifetime! All the things. Since returning I have received numerous requests wanting to know our day-by-day itinerary, so here we go!
SORRENTO – I chose for us to stay in Sorrento while visiting the Amalfi coast because it’s an easy town to take day trips out of, there’s a good mix of budget-friendly and luxury accommodations, and walking distance to restaurants, cafes, and shops.
Departure Day: We flew from Omaha to Chicago, Chicago to Munich, Munich to Naples. We left Omaha around 3:30pm CST and landed in Naples at 12:30pm GMT their time. * Pro tip – try to sleep on overnight flights to Europe so you’re not exhausted trying to get through your first day. I bought us all neck pillows, travel blankets, and I took a natural sleeping aide to help me fall asleep. Complimentary wine and beer on international flights are enticing, but not always the best way to start a long journey.
Day 1 (after landing in Naples): Our private transfer picked us up from the Naples airport and we made a stop in Pompeii before he took us to our hotel in Sorrento. It took us about two hours to walk through the ancient city and was a great first stop to discuss history with the girls. In hindsight, I wish we would’ve hired a tour guide to explain the city in more detail. After visiting Pompeii we checked in to the Hilton Sorrento Palace. The girls went swimming before we headed to the hotel restaurant, La Terrazza, where we took in the sunset, views of downtown, a few glasses of wine, and our first Italian meal.
Day 2: We booked a pizza making class and transfers were included. The class was held at the Tirabusciò cooking school about a 5-10 minute drive from downtown Sorrento. My oldest has celiac disease and they even provided gluten free flour so she could make her own pizza. We sat with people from Australia and the Netherlands, which made it fun connecting with people from other countries. This was such a great experience and highly recommend it to anyone visiting the area. The rest of our day we spent in downtown Sorrento exploring and shopping the quaint shops.
Day 3: We took a day trip to Positano. It’s about a 45 minute drive or ferry ride over to the cliffside village from Sorrento. It’s not often we get to take a ferry ride so we chose that mode of transportation. The walk to the ferry is an adventure in itself! We booked a smaller ferryboat where we sat in the front and got the best views of the Amalfi Coast. I booked beach chairs and umbrellas for our family ahead of time from Lido L ‘Incanto. Restaurants and shops are all close by, but this beach club offered wait service so we never left! I would recommend bringing water shoes if you visit Positano Spiaggia with it being a rocky beach. To end the day we took the scenic drive back to Sorrento. If you get car sick I highly recommend bringing Dramamine! Lots of turns along the windy, cliff-side roads.
Day 4: We booked another ferry to explore the island of Capri for the day. It’s a short 25 minute boat ride and approx $40/person round-trip. We had a private boat tour scheduled to take us around the island. We were planning to see the Blue Grotto, but the tide was too high and our guide informed us it is usually long lines, costly, and lasts about a minute. We decided to skip it and still had the most wonderful time. Our guide showed us other caves, took us through Lover’s Arch, and brought equipment for us to snorkel. The boat tour was by far our favorite experience while in Italy. Following the tour we ate lunch at Bar Il Gabbiano; the best lasagna and they even made my oldest fresh gluten free pasta! Following lunch we hopped in a convertible taxi to Anacapri (higher up on the island). From there we took a gondola up to the very top of the island and saw the most stunning, breathtaking panoramic views.
Day 5: Our last day in Sorrento…we decided to stay close and visit St. Peter’s Beach in Sorrento. It’s a smaller pebble beach where locals and tourists sunbathe. They have beach chair and umbrella rentals and a restaurant/bar if you want food and drinks. We had the most relaxing day and ending the evening by going to O’Parrucchiano La Favorita Restaurant. Gorgeous setting for dinner under lemon trees. There’s even a secret garden you can explore!
SANTORINI – I chose for us to stay in the town of Oia because I wanted to end our European journey in a peaceful, relaxing spot with breathtaking views. I knew we would find that there.
Day 6: Off to Santorini! After landing it was a quick 20 minute drive up to Oia, famous for it’s white washed buildings with blues domes. But first, we needed food! Immediately after getting dropped off we made a “quick stop” (nothing in Europe is quick – as Americans it’s something you have to get used to and when you do you fall in love with the slower pace) at Tramonto All Day Lounge next to our drop off area. They made one amazing club sandwich. In Greece they serve club sandwiches? I wasn’t expecting that either. In Europe they also eat their fries with mayo. Learned to love it, but still needed a side of ketchup! Next up….time to check into our villa.
While booking our villa I knew we were going to be in the center of town, but didn’t realize we were literally smack dab in the middle of everything! Restaurants, cafes, shops, and markets all within a 5-10 min walk from where we were staying. More importantly we had the most breathtaking panoramic views of the caldera and blue domes from our private terrace. Our villa was absolutely perfect for our family. It came with two bedrooms, two bathrooms, an extra room in the loft area, and a small kitchenette.
Day 7: We explored the village, went to the market for groceries, played card games, sunbathed on the terrace and were the most relaxed we’ve ever been as a family. This is all we wanted out of our Santorini vacation and we got it. I made dinner reservations for us at Karma Restaurant. We ordered their three dip combo with pitas, mastelo lamb, marinated chicken fillet, and gemista (Greek stuffed tomatoes). Greek food is fresh, light, and oh so delicious.
Day 8: We wanted another relaxing day in the villa so we did just that. Slept in, sunbathed, had wine on the terrace, then finally got ready for the day before heading out to dinner. I made reservations for us at Kyprida Restaurant. We ordered the pork souvlak, chicken souvlak, cheese ravioli, and houmous dip. Traditional Greek food at its finest. Yum! Finished the evening visiting more shops and getting ice cream and gelato at the village favorite, Lolita’s.
Day 9: Today we had a tour scheduled to take us around Santorini island through a preferred tour company I work with, Eclectic Greece. We were picked up in a Mercedes Maybach Sprinter – the nicest van I’ve ever been in! Our first stop we took in the views from the Firostefani village, which is an extension of Fira, the capital of Santorini. Then headed to the top of the island to visit the Prophet Elias Monastery. It is the only male monastery on the island and is one of the oldest, built in 1712. Then walked through the Megalochori Village one of the most picturesque villages on the island. I could walk the streets for days looking at all the different blue doors and beautiful pink flowers (called bougainvillea trees). Next stop we went to the Red Beach on the island, Kokkini Paralia. It’s extremely dangerous to swim there as they often have falling rock, but visitors either don’t read the signs or they don’t care and do it anyways. We opted to just take in the views from afar. Our last stop of the day was the Black Beach, Perívolos beach. Before reserving our beach chairs we had lunch at a beachside fine dining restaurant called Forty One. We could’ve stayed an entire day here. They had jetskis, parasailing, boat tours available nearby, but we didn’t have enough time to explore those options. After arriving back to the town of Oia, we ate at the thai restaurant, Paradox. They had some of the best thai food we’ve ever had – tom yum soup, fried won tons (crab rangoon), pork dumplings, pad thai, and shrimp fried rice were to die for. Final stop of the day was for frozen yogurt at Solo Gelato (our girls favorite). They ended up going here every day we were there.
Day 9: For brunch we were all hungry for more gyros so we headed to Niko’s Place, a short stroll from our villa. We then decided to walk off our full bellies so we went shopping (again), went to the Castle of Oia, then walked down to Amoudi Bay. It’s a couple hundred steps down below the castle ruins area. We weren’t prepared for this little hike and wish we would’ve all been wearing tennis shoes. Once we made it down to the bottom it was worth it. There are restaurants and bars you could sit and take in the views. The sunset from this location would be a perfect spot! We decided to keep exploring and walked another 5-10 minutes through a rocky path were we found people cliff diving. It was pretty chilly by this point and the water was rough so we decided to just sit back and watch others do it. The tough part was walking back up the two hundred steps! You could take donkey rides back up, but we decided not to. We ended the day by going to Melitini Tapas Restaurant for traditional Greek dinner and sunset views. We had dips with pita, fried potatoes, smoked chicken filet, pork filet, homemade pasta, fish, and chocolate mousse.
Day 10: Our last day on the island. We first went to the café we would visit each morning for coffee, Terpsi in Oia. Instead of getting coffee we got ouzo to sip on while taking one final leisurely stroll through the town. We then picked up an art piece to take home for the house, got more frozen yogurt, purchased souvenirs, went back to Tramonto restaurant where we had lunch on our first day in Santorini to reminisce on the trip and to take in sunset views. We had our last dinner at Pelekanos (a restaurant directly above our villa) and met our favorite waitress of the trip, Zoe.
If you or someone you know is looking to visit these destinations, feel free to reach out! I would love to help build a custom itinerary to (what now are) two of my favorite places. Moani
Nova Vacations 