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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Where to stay
J.K. Place Roma
Housed in Rome’s former school of architecture, J.K. Place Roma is a boutique hotel with an abundance of chic style and warm hospitality.
Fora Perks
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$100 food / beverage credit.
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Breakfast daily.
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Upgrade & extended check-in/out whenever possible.
Hotel Il Pellicano
Cliff-top property with posh rooms and suites offering views of the Tyrrhenian Sea.
Fora Perks
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$100 hotel / resort credit.
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Breakfast daily.
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Upgrade & extended check-in/out whenever possible.
Rosewood Castiglion del Bosco
Seasonal hotel set on a 2,000-hectare estate with refined suites in the heart of Tuscany.
Fora Perks
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$100 food / beverage credit.
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Breakfast daily.
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Upgrade & extended check-in/out whenever possible.
The Place Firenze
In the heart of Florence, deeply connected to its daily life, artistic heritage and lively cultural scene, The Place is a unique accommodation that makes you feel at home.
Fora Perks
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$100 food / beverage credit.
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Breakfast daily.
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Upgrade & extended check-in/out whenever possible.
Four Seasons Hotel Firenze
An oasis in the city center, home to an Old World style, a Michelin-starred restaurant and Florence’s largest private garden.
Fora Perks
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$100 hotel / resort credit.
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Breakfast daily.
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Upgrade & extended check-in/out whenever possible.
Unlock perks by contacting Bianca to book your trip.
Day 1: Arrive in Rome
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
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
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
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
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
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
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
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
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!
Travel Advisor
Bianca Ragusa
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This guide is part of our ongoing series on travel to Tuscany.