When thinking about romantic destinations around the world, Tuscany in Italy is typically one of the top that comes to mind.

From preserved medieval architecture to spa-focused towns to valleys lush with olive trees and Sangiovese grapevines, there is much for couples in love to enjoy.

To help you experience the best of this Italian region with your someone special, here are the top romantic things to do in Tuscany.

1. Stay in a 12th-Century Castle

When you picture Tuscany, it’s likely a few things come to mind:

Delicious olive trees, vineyards of Sangiovese, colorful citrus groves and rolling hills dotted with historic castles.

Instead of hopping in your car and driving through this beautiful setting, immerse yourself in it by staying at a castle in the countryside.

Castello di Gabbiano is a 12th-century castle once home to important Florentine families like the Bardi and the Soderini. The romance of the structure is undeniable, with its impressive tower, fortified stone walls, red-carpeted stairways, and relaxing pergola and gardens.

In the restaurant—an 18th-century brick farmhouse—couples can savor a traditional Tuscan meal paired with estate wines while taking in the stunning view. Be sure to take a tour of Castello di Gabbiano’s vineyards—it’s one of the original estates to produce Chianti Classico and has made the Tuscan staple since the 14th century.

Other romantic experiences at Gabbiano include cooking classes; olive oil harvesting and pressing; truffle hunting; learning about wine grapes in their educational garden; blind, barrel, vertical and structured wine tastings; and ceramic enameling courses.

Tuscan bean salad. Photo courtesy of travellight via Shutterstock.

2. Enjoy Thousands Of Italian Wines At Piazza del Vino

In Florence, you’ll find a restaurant unique in Tuscany:

Piazza del Vino, one of the best restaurants in Tuscany.

While most restaurants in the region pair wines with food, here they match the food to the wine.

As soon as you and your special someone walk into the space—with its thick brick walls, high ceilings and rustic wooden accents—you’ll notice the thousands of wine bottles showcased on the walls.

Servers are passionate and knowledgeable about wine and can help you pair these with traditional dishes from various regions in Italy. That being said, the menu is laid out in a way that makes it easy for you to pair wines and meals from the same area on your own (so you can really impress your partner).

Regulars have the option of keeping their own small wine cellar on-site, and those who would rather have a glass than a bottle can make use of their self-serve wine dispenser. We recommend opting for their wine and food degustation menu, so you can try a little bit of everything.

3. Take A Cooking Class

Nothing bonds two people like trying something new together, and taking a traditional Tuscan cooking class is a great way to do this and immerse yourself in local culture.

There’s no shortage of cooking classes in Tuscany, especially at the many agriturismos offering sustainable farm-to-table experiences.

Castello di Gabbiano features an array of cooking courses at their restaurant, Il Cavaliere, including Tuscan Peasant Cuisine, Food and Wine in Harmony, Oil in Cooking and Renaissance Cuisine.

Another excellent venue for taking traditional Tuscan cooking classes is Castelfalfi, which hosts culinary classes through Il Rosmarino, their signature eatery.

Learn to make homemade pasta, flavorful sauces, pizza, focaccia and typical dishes like Pappa al Pomodoro and Peposo di Manzo.

Chianti. Photo courtesy of Samot via Shutterstock

4. Drive The Chianti Classico Road

The Chianti Classico Road, or Road 222, takes you through the beautiful, Sangiovese-soaked Chianti Classico Wine Region.

It extends roughly north and south between Florence and Siena, although there are additional road options going east and west. While it’s possible to drive straight through in less than two hours, a more romantic experience is taking a few days, stopping off at the different farms and wineries.

The above-mentioned Castello di Gabbiano is in the Chianti Classico Region, while on the road you’ll find a number of other worthwhile stops, some of which include Val delle Corti, Villa Pomona, Podere Terreno and Fattoria Viticcio.

If you’re an active couple, opt for a cycling and wine tasting tour through the region from I Bike Tuscany.

5. Learn The Art Of Olive Oil

There are many myths about olive oil. Did you know that extra virgin olive oil, the ubiquitous EVOO, isn’t the highest quality?

Premium extra virgin is the best—the olives have been pressed within 12 hours of being picked. Moreover, did you know olives have a vintage?

But unlike with wine, olive oil does not get better with age—it oxidizes. Seeing how olives are harvested and pressed can help you debunk these myths while sampling some of the world’s highest quality olive oil.

Some agriturismos offering this experience include Castello di Gabbiano, Castelfalfi, Frantoio Landi Olive Mill, Casaloste and Castello di Volpaia.

San Gimignano
San Gimignano. Photo courtesy of leoks via Shutterstock

6. Stroll Through San Gimignano

The Town of Fine Towers is a UNESCO World Heritage site and strolling through this medieval hill town lined with 13th-century walls is a truly romantic experience. Take in the 14 well-preserved towers—the only ones remaining from the original 72—as well as the many piazzas and churches that litter San Gimignano.

Visit San Gimignano 1300, a museum that can give you background into Tuscany’s architecture and heritage for a better idea of what you’re seeing.

Tour the Church of Sant’Agostino, see the beautiful artwork inside the Pinacoteca Civica, visit San Gimignano’s tallest tower (Torre Grossa), sample world-renowned gelato from Dondoli’s shop in Piazza della Cisterna, and take a countryside hike around the town.

7. Art, Gardens And Chocolate In Florence

There are many romantic experiences to be had in Florence. After viewing masterpieces such as Botticelli’s Birth of Venus at the Uffizi Gallery, take a stroll through the colorful Boboli Gardens, littered with fountains, statues and flowers.

Next, make your way over the famous Ponte Vecchio Bridge and add your own love lock to the collection sealed by passionate lovers.

Having a picnic at Pitti Palace, taking in a sunset at San Miniato al Monte Basilica to the sound of the monks chanting, viewing the city from the Piazzale Michelangelo, walking along the Arno River, and wine tasting at an ambient venue like Pitti Gola e Cantina are just a few of the many other romantic experiences to have in Florence.

Montecatini Terme
Montecatini Terme. Photo courtesy of Flegere via Shutterstock.

8. Relax In Montecatini Terme

Known for its rich spa and wellness offerings, Montecatini Terme is a great place to indulge with your sweetheart.

Home to curative thermal waters, the town features both historical and modern spas. The most popular spa is the 18th-century Tettuccio Terme, a grand spa offering new-age treatments like hydroponic therapy, inhalation therapy, and balneotherapy.

For a spa experience, you can share with your sweetie, the Grand Hotel & La Pace SPA features a Romantic & Relaxing Escape for two, including a hydro massage and Turkish bath in a spa suite, aromatherapy body massage and scalp massage.

Don’t leave Montecatini Terme without taking a cable-car ride up to Montecatini Alto for aerial views of the Tuscan countryside and towns.

What experiences make you fall in love with Tuscany?

Further Italy Exploration:

Vineyard Work In Italy: A Fun & Unique Volunteer Experience

Learning The Art Of Fresco In Florence

10 Awesome Places To Visit In Italy

Jessica Festa

Jessica Festa is the editor of Epicure & Culture as well as Jessie on a Journey. She enjoys getting lost in new cities and having experiences you don’t read about in guidebooks. Some of her favorite travel experiences have been teaching English in Thailand, trekking her way through South America, backpacking Europe solo, road tripping through Australia, agritouring through Tuscany, and volunteering in Ghana.

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  1. Good post with amazing pictures! Makes me want to got Tuscany!

    1. @Curious Desi: Such an amazing place!

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