Curator’s statement
The Italian way of life is all about slowing down and enjoying the sweetness of doing nothing. To me, nothing sounds sweeter than a honeymoon (or anniversary!) with the one you love savoring the moment and embracing the Italian way of life. And while you won't exactly "do nothing" - sipping Chianti, looking over the Tuscan countryside or getting lost in the streets of Firenze can have that effect. Here's how to savor the sweet Tuscany region on the perfect romantic trip.
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Where to stay
COMO Castello Del Nero
Spacious rooms with original 18th century frescoes overlooking the surrounding hills, woods, lawns and lines of Tuscan cypress trees of the Chianti wine region.
Castello di Casole
La dolce vita brought to life on 4,200 acres of fairytale Tuscan countryside.
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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.
Castello Banfi Il Borgo, Relais & Chateaux
Castle accommodations on a hillside in Tuscany.
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VIP welcome & amenity.
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Breakfast daily.
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Upgrade & extended check-in/out whenever possible.
Relais Sant'Elena | Relais di Charme, Vacanze Bibbona Toscana
An earthy Tuscan escape on 580 rolling acres, with 16 richly decorated rooms, prized gardens and homemade meals.
Splendido Mare, A Belmond Hotel, Portofino
Beloved by Elizabeth Taylor, this storied Portofino stay is a beacon of bygone-age glamour and service, with unforgettable views across the Mediterranean Sea.
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.
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Day 1: Getting to Know Tuscany
Your first day in Tuscany should be spent relaxing at your gorgeous hotel — my preference is a luxury castle stay. Most offer beautiful views of the countryside, pools and spa amenities and unique experiences specific to the region. My favorite is truffle hunting. You will tag along with the famous truffle hunter dogs and watch them find magic! Many experiences offer a special truffle themed lunch as well. For the afternoon, enjoy a wine tasting before a delicious Italian dinner.
Day 2: Florence
Spend the day exploring the city and all of its masterpieces: The David, the Duomo, Uffizi Gallery and Ponte Vecchio. Depending on the time of year, some of these experiences are best with a guide and a skip the line option. Florence Food Tours is another great way to see a variety of things and try many local flavors. Don't forget to visit a famous wine window (used for hundreds of years in Florence - owners can avoid opening a shop and taxes but also was popular during plaque (and COVID!). Head to Piazzale Michelangelo for sunset.
Day 3: Cinque Terre
The infamous five villages built into the coastal cliffs. The hike between the five villages will take a full day so plan an extra early start. Also, you now need to reserve a pass in advance so be sure to plan ahead with advisor who know the region and can help! If hiking the five isn't right for you, spend the day exploring one or two villages and take the train between. Have your camera ready!
Day 4: Wine
You can't miss the delicious wine of the region. Hire a driver for the day and bop between several wineries for tours and tastings. Don't skip lunch! Many of the wineries offer incredible lunch menus complete with wine pairings.
Day 5: Small Towns
The Tuscan region is scattered with some really beautiful, medieval villages. Depending on where you are staying, you can easily visit several in a day! My favorites are Lucca, Siena, Volterra, San Gimignano, Castellina in Chianti and Montepulciano.
Need to Know
For more travel tips, check out Travel Advisor Jennifer Schwartz’s guide, Guide to Picturesque Picnics In and Around Rome.
![Advisor - Caroline Bernthal](https://media.foratravel.com/image/upload/v1711119338/contentful-migration/advisors/image/05a2c8ff4a0c-89F5C215_F6FB_4039_BF60_66C79F0C19D9.jpg)
Travel Advisor
Caroline Bernthal
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This guide is part of our ongoing series on travel to Italy.