10-Day Dreamy Tuscan Honeymoon

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Advisor - Bianca Ragusa
Curated By

Bianca Ragusa

  • Tuscany

  • Couples Travel

  • Food & Wine

  • Honeymoons

  • Florence

  • Rome

  • History

  • Vineyard

  • Romantic

  • Foodie

hotel with a round pool in the Italian countryside
Curator’s statement

Tuscany is so special to me because it's where my husband and I went on one of our first trips together. Tuscany is known for its rich history, rolling vineyards, and amazing cuisine. It's the most dreamy place surrounded by romance (and wine!) We could not have picked a better location for our Honeymoon.

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Day 1: Arrive in Rome

The Spanish Steps is an iconic Roman landmark, a monumental staircase adorned with elegance and history, connecting Piazza di Spagna to the Trinità dei Monti church.

Most international travelers will arrive in the morning. Check into your hotel and get settled in. I recommend staying at J.K. Place Roma. Since we had limited time here, we decided to stay in the heart of the city, steps away from the Spanish Steps. Grab lunch at Emma. Make sure to order the pizza with their fresh special cheese!

Then head out to sightsee for the day. No trip to Rome is complete without a visit to the Colosseum.

After, head over to the nearby Roman Forum. I’d highly recommend purchasing skip the line tickets in advance. (Pro tip: to avoid heavy crowds during the day, go see the famous sights at night!)

We then explored a bit more before heading to the Trevi fountain to make a wish! After a day of exploring, we made our way back to the hotel to wind down before heading out to dinner at Cul de Sac. Did not disappoint and would highly recommend the wine pairing!

Day 2: Explore Rome

10-Day Dreamy Tuscan Honeymoon - Day 2: Explore Rome

If you haven’t been to Rome before, wake up early to visit the Vatican. Purchasing tickets in advance is a must! The Vatican will take up most of the morning.

After, we worked up an appetite and had lunch at Osteria da Fortunata. It's one of the best-known pasta places in Rome and they literally make the pasta right in front of you!

After our amazing lunch, we walked around and got lost exploring the city. Before going to dinner, Apertivos is a must in Italy. Head over and check out the brand new and stunning Six Senses Rome for an Aperol spritz on their rooftop bar, NOTOS, before heading to dinner at Taverna Trilussa!

Day 3: Hotel il Pellicano

harbor town

Head to the train station and take the train from Orbetello, where your driver will meet you and take you to Hotel il Pellicano. It’s situated on the coast of Tuscany with its own private beach.

Once you arrive, you will instantly be transported to the 1960’s retro glamour era. Every detail of this place is impeccable. Once you check in, head to the pool or beach, where you can grab lunch.

Spend the day relaxing in the Mediterranean sun! Apertivos are huge here, they have live music every night and everyone in the hotel gathers pre-dinner to grab drinks, it’s magical.

We went to the Pelligrill for our first night and had some of the best seafood we have ever had. My husband still raves about how fresh the oysters were!

Day 4: Relaxing day at Il Pellicano

wine cellar

At Il Pellicano everyone starts their day with breakfast, and for good reason. This is probably the best breakfast spread I have ever had. There are plenty of things to fill your day. You can opt to head to the gym, play some tennis, and enjoy the spa if you want to do something other than lay on the beach. We chose this hotel to completely disconnect and relax so we opted to take full advantage of the private beach and take a dip into the ocean after playing a game of tennis! We wanted a true gem that was off the beaten path and we couldn’t have picked a better place. There is a beautiful wine cellar as well, where we had a private tasting before dinner. You are in Tuscany, after all. You can never do too many wine tastings.

For our last night, we went to the more formal Il Pellicano for dinner which has one Michelin star. This was amazing as well, however we preferred the more casual Pelligrill which was outside and had an ocean view.

Day 5: Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco is situated within one of the oldest and best-preserved estates in Tuscany

The next morning, we made sure to grab breakfast before checking out and heading to Rosewood Castiglion del Bosco. Once we checked in, we immediately headed to our first wine tasting. The hotel is in Montalcino on 5000 acres of beauty. It has been converted from a 900-year-old estate and has its own private vineyard. It’s truly breathtaking! After the tasting, we relaxed in our room before grabbing Apertivos in the courtyard and then heading to dinner.

Day 6: Rosewood Castiglion del Bosco

church in the countryside of italy

Wake up and grab breakfast at the hotel and head out for truffle hunting followed by wine tasting and lunch in the city of Montalcino. This will take about half of the day; afterwards, we relaxed at the pool which looks over the Tuscan hills. Make sure to get the Limoncello cocktail at the pool bar. I still dream of it to this day! For dinner, we opted to go to the more casual restaurant of the two, Osteria La Canonica.

Day 7: Pasta cooking class

Osteria da Fortunata's handmade pasta.

On our last day, we took an amazing cooking class that taught us how to make fresh pasta! Classes started in the garden where we picked fresh herbs and vegetables that we used to make our meals, which turned out to be amazing. After that, we spent the remainder of the day at the pool and relaxed until dinner. It was the perfect day!

Day 8: Florence

Aerial view of the Duomo in Florence showcasing the cathedral's incredible size. (Photo by Fede Roveda)

The next morning we woke up and ate breakfast at the hotel and then was picked up by our driver and made our way to Florence. We checked into our hotel, The Place Firenze, which was steps away from the Duomo.

After checking in we immediately decided to explore the city. We started by going to grabbing lunch at Antica Noe. There is always a line, but worth the wait for one of the best paninis you will ever have.

After lunch, we walked around and shopped. Florence is just one of those places you can walk around and get lost in. This was my fourth time here and each time I discover something new!

For dinner, we went to one of our favorite restaurants, La Giostra. This is a definite must! Reservations in advance are necessary. Make sure to get the pear ravioli and burrata- thank me later!

Day 9 & 10: Museums and pizza

pizza coming out of an oven

On our final day, we decided to wake up early and go see the statue of Michael. Skip-the-line tickets are recommended! After that, we walked around and ate lunch at Gustapizza, which has the most delicious pizza! After lunch, we shopped around for a bit before heading back to the hotel to pack for our flight home. It's always happy hour in Italy, so we decided to grab some Apertivos before our last dinner at Il Latini.

On day 10, fly home!

Advisor - Bianca Ragusa

Travel Advisor

Bianca Ragusa

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This guide is part of our ongoing series on travel to Tuscany.