Two-Week Itinerary for Italy & Santorini

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!)
    • 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)
    • 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)
  • 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:

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The adorable town of Positano in the Amalfi Coast

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Sunset in Florence from the Piazza Michelangelo 

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View of Firenze from the Uffizi Gallery

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Rolling hills of Tuscany. View from Fonte de Medici. No words. 

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Trevi Fountain, Rome

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Santorini views from Imerovigli 

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Sunset at Oia, Santorini

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