Ever since my husband and I got engaged, we’ve been dreaming about an extended honeymoon somewhere in Europe. We’ve both traveled to Europe separately, but couldn’t wait to experience its magic together. I spent four years in Paris growing up and planned a trip to Barcelona after graduating from college, while he had studied abroad in Madrid. With our hectic schedules, we couldn’t make a honeymoon work right after the wedding, but boy was it worth the two-year wait.
We explored a couple different countries while researching for our trip, and almost decided against Italy. We were worried it would be too touristy, and it just felt so cliched to travel to Italy for our honeymoon after seeing so many of our friends doing the same. We’ve both also been to Italy during our younger years, and considered traveling somewhere more off the beaten path. Alas, our love for fresh pasta, vino and Italian culture was too strong, and I’m SO glad we decided to spend the majority of our trip in Italy. It’s simply exquisite. Santorini has always been at the top of my bucket list, so I convinced my husband to spend the last few days of our vacation there since we were going to be so close. I definitely need to plan a separate trip to Greece to experience its culture in its entirety, but we’re incredibly grateful that we got to spend a few days in Santorini during our honeymoon. It is beyond words.
Here’s how we laid out our two weeks in Italy & Santorini. September is the perfect time to visit Italy, because it’s at the end of tourist season and the weather starts to cool down ever so slightly (but still warm enough for beaches). We wanted to get a good feel for the country by visiting a variety of different cities, but we also didn’t want to be overwhelmed by packing our bags every 1-2 days. We wanted a good mix of beach towns, wine country, big cities, culture and adventure with things to constantly do. We like to be on the go when we’re on vacation rather than beach bumming for a week straight, so this itinerary worked really well for us and gave us a sense of places we want to visit again for a longer period of time. We also LOVED all the hotels/B&Bs that we stayed at, so I’ve linked details to our accommodations. Okay, enough rambling – here we go!
- DAY 1: Fly into Naples, rent a car (with a driver – you don’t want to be driving on your own here) and drive directly to the picturesque town of Positano for two days. We’re not huge beach people and wanted to spend more time in other places in Italy and in Santorini, so we decided to spend all our time in Positano rather than town-hopping around the Amalfi Coast.
- Positano accommodation: Villa La Tartana (cute little no-frills B&B steps away from the Spiagga Grande)
- Tip: Visit Le Sirenuse for a gorgeous view of Positano’s colorful homes. Rent a private speed boat at Spiagga Grande (super affordable for just an hour or two) for the most breathtaking and luxurious views of the Amalfi Coast. You can drive around the coast with a bottle of Prosecco, visit private beaches, and go swimming. The views of Positano from the boat just can’t be beat.
- Foodie highlights: We weren’t super adventurous with food in Positano because we were there for such a short period of time but we liked Chez Black for fresh seafood and a stellar waterfront view. Yes, it’s super touristy and on the pricey side, but worth it for one meal.
- DAY 2: Positano – sight seeing, beach bumming
- DAY 3: Positano in the morning, then take a car back to Naples and a train to Florence
- Florence accommodation: Le Stanze di Caterina (steps away from the Duomo with beautiful, art-inspired rooms)
- DAY 4: Florence – sight seeing (Uffizi Gallery, Scuola del Cuoio – Florence’s leather school with amazing leather products, and sunset at Piazzale Michelangelo)
- Foodie highlights: Osteria Santo Spirito for a more local feel and Trattoria ZaZa for unbelievable truffle pastas.
- DAY 5: Florence – sight seeing till the late afternoon (Mercato Centrale for fabulous lunch options and Accademia for the gorgeous David), then rent a car to drive to Tuscany
- Tuscany accommodation: Fonte de Medici (We got an incredible deal through Jetsetter– the most gorgeous Tuscan villas EVER! A little remote, but totally worth it for the property)
- Foodie highlights: Lamole di Lamole. Must visit for the most mouthwatering Florentine steak ever. Amazing spot.
- DAY 6: Tuscany – wine tasting and visiting little Medieval towns
- DAY 7: Tuscany/day trip to Siena
- DAY 8: Tuscany, then drive to Rome
- Rome accommodation: Augustana House (Super clean, no-frills B&B located on a quieter, less touristy part of the city. Nicest staff, but I do wish we had stayed in the Trastavere neighborhood instead for its charming alleyways and boho feel!)
- Foodie highlights: We arrived in Rome with pretty low expectations (“It’s too hot! Too touristy!”) but we absolutely LOVED the city. The food in particular was absolutely stellar; the best we had in the country. Highly recommend following Romewise.com for restaurant suggestions and making reservations EARLY – I’m still dreaming about my pasta dishes from Osteria del Sostegno and Roberto e Loretta. Rome is heaven for pasta, bacon and tiramisu lovers. Mmm!
- DAY 9: Rome – sight seeing (Trevi Fountain and the Caesar Shuffle – Colosseum, Roman Forum, and Pantheon)
- DAY 10: Rome – sight seeing (the Vatican – absolutely incredible)
- DAY 11: Rome in the morning, then flight to Santorini
- Santorini accommodation: The Majestic Hotel (just outside Fira – BEAUTIFUL hotel, but we would have preferred to stay in Oia or Imerovigli instead)
- Tip: Best way to explore the entire island is by renting an ATV! So much fun, and you come across so many lovely little private beaches with family-owned seafood restaurants. Some of the spots we stumbled upon were just magnificent. Santorini is too beautiful for words.
- DAY 12: Santorini – sight seeing (Sunset Cruise – highly recommend splurging for one with fewer people on the boat)
- DAY 13: Santorini – sight seeing (exploring the towns of Fira, Imerovigli, and Oia)
- DAY 14: Santorini, then flight back to the U.S. via Rome
Sigh, can I please go back already? Hope this itinerary was helpful for your planning – leave me a comment if you have any questions! And just so this post isn’t ALL words, here are some of my favorite pictures from our trip:
The adorable town of Positano in the Amalfi Coast
Sunset in Florence from the Piazza Michelangelo
View of Firenze from the Uffizi Gallery
Rolling hills of Tuscany. View from Fonte de Medici. No words.
Trevi Fountain, Rome
Santorini views from Imerovigli
Sunset at Oia, Santorini
12 thoughts on “Two-Week Itinerary for Italy & Santorini”
Thanks so much for recommending my website! I’m so pleased you found it helpful and enjoyed my restaurant suggestions!
LOVED your website! Been raving about it to everyone visiting Rome!
Thanks! Any recommendations for the car/driver rental to Positano, or through Tuscany? Also, did you utilize a travel agent at all?
Hi Chad – thanks for checking out my post! Ah, I can’t remember the name of the rental company we used for Positano but found them through some quick research on TripAdvisor. For the drive from Rome to Tuscany, we rented a car through National Car Rental. We didn’t use a travel agent – we love creating our own itinerary!
Was three days enough visiting the Amalfi? Which did you enjoy more, Santorini or Amalfi? Thanks.
Hi there – so sorry for the late response! Three days was plenty for Positano, but if you’re planning on visiting more towns around the Amalfi then I would recommend more days. We wanted to squeeze in more cities around Italy so got our fill of the Amalfi in three days. Both Santorini and Amalfi are beautiful and unique in different ways, it’s hard to pick one. Santorini really is just epic and even more beautiful than photographs can convey.
Great post, super helpful! I’m taking a trip with my girlfriend in July we are going to have 10 days between London, Paris, and Switzerland and then 10-11 days between Italy and Santorini- any recommendations on how we should compress your itinerary? Thanks so much!
I’m so glad it was helpful! Thank you for reading. If you only have 10-11 days, I would suggest picking between Amalfi Coast and Santorini since they’ll both have similar vibes. I would probably stick to Florence/Tuscany, Rome, and Santorini and save Amalfi Coast for a separate trip!
This was so helpful! We are planning our delayed honeymoon for this fall. Is there anything looking back now that you would change, add, do differently? We will only have 10 days and want to enjoy, but don’t want to feel rushed like you said. Any input you have is welcomed and appreciated! TIA 🙂
Thanks, Emily! So glad this post is helpful. This itinerary worked well for us since we wanted a taste of each place and wanted to explore as many areas as possible. That said, I’ve heard wonderful things about Ravello and other towns in the Amalfi Coast that I would have loved to visit in addition to Positano!
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