The Most Romantic Places to Stay in Tuscany for Honeymoons or Romantic Getaways

Enjoy our inside guide to planning romantic getaways in Tuscany.

The Most Romantic Places to Stay in Tuscany

Italy already sizzles with the charisma of romance and the dreamy landscape and inspiring history of Tuscany make it an incredibly romantic place to visit. Throw in rose gardens, Michelin starred dining, olive oil and wine and it’s enough to make you fall in love with life, never mind your partner.

The most romantic places in Tuscany are shaped by quiet pleasures: walking back through a medieval street after dinner, opening shutters onto vineyards, or sharing a bottle of Brunello as the light fades over the hills.

Here’s our guide to how to plan a romantic getaway or honeymoon here, complete with finding the most romantic accommodation in Tuscany that suits you.

Sunset over the Duomo in Florence skyline

Florence: Romance in the Heart of Art and History

Florence is the big hitting city in the area, although it bears no resemblance whatsoever to the glassy skyscrapers and concrete jungles of the 20th century.

This is the birthplace of the Renaissance and a terracotta dream. As long as you avoid the summer crowds, the heart of Florence remains one of the most romantic places in Tuscany, not because it tries to be, but because of how effortlessly history and daily life coexist. Wandering across the Arno at dusk on the Ponte Vecchio and watching the light soften around the Duomo is almost enough to make anyone propose.

Areas located in the Oltrarno offer a more local rhythm, with wine bars, workshops, and neighbourhood restaurants tucked behind unassuming façades.

Florence also works beautifully for a weekend in Tuscany. Its compact scale means you can experience art, food and wine, and views of the city without rushing, making it one of the most romantic urban destinations in Italy.

See how to spend one day in Florence.

Val d’Orcia: Tuscany at Its Most Poetic

If Tuscany has a landscape that feels purpose-built for romance, it is the Val d’Orcia. This UNESCO-listed region is defined by rolling hills, isolated farmhouses, and roads that seem designed for unhurried drives. The beauty here is not dramatic but cumulative, revealed through changing light and wide, open views of the Tuscan countryside.

Towns such as Pienza and San Quirico d’Orcia are small enough to feel personal. And after hiking or driving through the Tuscan countryside, you can spend your evenings lingering over dinner, and watching locals gather in the square.

The nearby thermal springs at Saturnia allow you to snuggle in together, surrounded by countryside views with steam rising into the evening air.

City skyline of Siena with terracotta rooftops

Siena: Medieval Grandeur and Shared Silence

Siena is one of the most romantic destinations in Tuscany for couples drawn to history and atmosphere. Its medieval centre, built around the famous piazza del Campo, rewards those who stay overnight.

Walking through Siena’s narrow streets at night, passing candlelit windows and softly lit churches, provides another perfection location for a proposal. The city’s compact scale encourages walking rather than planning, and shared evenings become the focus rather than sightseeing. Siena is especially appealing for a romantic weekend or as part of a slower Tuscany travel route.

See how to plan the perfect Tuscany itinerary here.

Volterra: A Hilltop Town with Depth

Perched on a hill above the surrounding countryside, Volterra offers one of the most understated romantic experiences in Tuscany. Less visited than some of its neighbours, it retains a sense of authenticity that makes it feel, well, rather lovely.

Volterra’s Etruscan history, weathered stone buildings, and long views across the Tuscan hills make it perfect for a romantic picnic by day and sunset spotting spot by night.

Chianti: Vineyards and Wine Tastings

Push images of Hannibal Lecter out of your mind for a moment, and instead focus on the centuries of winemaking traditions instead. Vineyards stretch across the Tuscan hills, dotted with wineries where you can really get to grips with great wine and olive oil.

Recommended wineries to visit include Castello di Ama, near Gaiole, where contemporary art installations sit quietly among the vines, and Badia a Coltibuono, a former abbey, which now serves excellent wine and olive oil.

Lucca

Encircled by Renaissance walls, Lucca sits somewhere between Florence and Montepulciano and other Tuscan villages in terms of size. You’ll find the fingerprints of the Renaissance here, of course, as well some great gelato and the chance to cycle along the ramparts at sunset.

Find unusual things to do in Tuscany here.

The Tuscan Coast and Argentario

Yes, Tuscany has a coast – and it’s a gorgeous one at that. Around Monte Argentario, the landscape shifts from vineyards and dreamy, undulating hills to rocky headlands and harbours. Think salt air, seafood dinners, and sunset views over the water.

The coast works well as part of a longer Italy trip, when you can venture further afield to either the Cinque Terre or Amalfi Coast.

Staying in a Romantic Villa with a Pool

Let’s face it, you can’t get much more romantic than having your own private villa and pool.

Surrounded by vineyards or olive groves, villas with private pools in Tuscany offer space, silence, and privacy. For honeymoons or longer stays, a villa can be the most romantic place to stay in Tuscany, or on Valentine’s Day for a particularly memorable milestone or anniversary.

Practical Travel Tips for Visiting Tuscany

Shoulder seasons in spring and autumn balance weather and atmosphere, while winter offers quieter towns and shorter queues at the top sights, making it easier to take a day trip to Pisa or Florence. The exquisite tuscan cuisine is great all year round, and while the vineyards can appear a little bleak and blackened in winter, wine tasting itself doesn’t depend upon the weather.

For countryside stays, vineyards, and villas, you’ll need a car.

Have an unforgettable stay.