The Most Romantic Things to do in Tuscany

From the rolling hills of Chianti to medieval villages frozen in time, every corner of this region offers the chance to experience pure magic.

By staying at Hotel Ilaria in Lucca, nestled within the city’s historic 16th-century walls, you’ll be perfectly positioned to discover Tuscany’s most romantic destinations. Its prime location, in the heart of the old town and just minutes from major attractions, makes it easy to explore both the city and its surroundings. After a day filled with art and nature, return to the hotel’s warm, relaxing atmosphere, ideal for a romantic stay. In fact, Lucca is the perfect destination for an unforgettable Valentine’s Day escape.
 
Discover the most romantic experiences Tuscany has to offer, starting from Hotel Ilaria.

Your romantic journey begins right here in Lucca, just steps from our hotel in the historic center. Wander down Via Fillungo, the city’s elegant main thoroughfare, where a charming array of boutiques, cafés, and artisan shops create an enchanting atmosphere.
For a truly memorable moment, climb the Guinigi Tower, famous for its rooftop garden adorned with centuries-old holm oaks. From the top, you’ll enjoy breathtaking views of Lucca and the surrounding hills. Capture your love with a sunset photo—an unforgettable keepsake to cherish forever.

Florence, the cradle of the Renaissance, is the perfect destination for a romantic getaway in Tuscany. Stroll along the Ponte Vecchio, its evening lights softly glowing, and gaze at the moonlit reflections on the Arno River—a truly magical experience.
For a private, romantic moment, visit Piazzale Michelangelo at sunset. The panoramic view of the city, with Brunelleschi’s dome and Giotto’s bell tower, is simply spectacular. End your evening with a candlelit dinner at a traditional trattoria or a gourmet restaurant, pairing Tuscan flavors with a fine local wine.

Chianti is synonymous with dreamy landscapes and exquisite wines. If you want to impress your partner, plan a wine experience amidst the rolling hills of Chianti. Arrange a picnic at one of the many vineyards in the area, where you can savor top-tier wines alongside local cheeses, cured meats, and freshly baked bread.
For an extra touch of romance, choose a spot with views of the vineyards and cypress-lined hills. It’s the perfect setting to toast to your love, surrounded by aromas and colors that could easily belong to a painting.

San Gimignano, with its towering medieval skyline, feels like a setting straight out of a fairytale. Stroll through the cobblestone streets adorned with flower-draped balconies, making your way to Piazza della Cisterna, where time seems to stand still.
If you’re visiting as a couple, don’t miss the climb up the Torre Grossa. The view from the top is a breathtaking reward and fills the heart with joy. Before heading back, indulge in artisanal gelato from one of San Gimignano’s historic gelaterias—a sweet memory to end your day.

The Val d’Orcia is one of Tuscany’s most iconic areas, celebrated for its stunning landscapes and picturesque villages. For a moment of pure romance, visit Pienza, known as the “ideal city” of the Renaissance.
From here, watch the sunset over the rolling hills dotted with farmhouses and towering cypresses. The view is so idyllic it feels like a painting, making it the perfect backdrop for a romantic escape to remember.

Pisa is world-famous for its Leaning Tower, but the city offers so much more for couples to enjoy. Stroll through the splendid Piazza dei Miracoli, where the harmonious blend of the Cathedral, Baptistery, and Tower creates an atmosphere that feels like an embrace between art and architecture.
Take a leisurely walk hand-in-hand along the Arno River, where the historic palaces are reflected in the water. It’s the ideal spot to exchange promises of love, don’t you think?

The Medici villas, UNESCO World Heritage sites, embody the luxury and elegance of the Florentine Renaissance. Among the most romantic are Villa di Poggio a Caiano and Villa La Petraia, both surrounded by stunning gardens. Get lost in the symmetrical designs of the Italian-style gardens, where nature and architecture blend harmoniously. These villas provide the perfect backdrop for moments of intimacy and romance in the open air.

After exploring Tuscany’s wonders, come back to Lucca and let the welcoming staff and top-tier services at Hotel Ilaria pamper you. Book your stay and experience an unforgettable journey in one of Italy’s most enchanting regions.