Romantic things to do in Tuscany

The most romantic things to do in Tuscany

by | Luxury travel guides

Italy is top of the list when it comes to romantic destinations. More specifically, Tuscany – with its rolling hills, medieval cobbled streets and Michelin-star restaurants – is the ultimate setting for a loved-up escape.

Having got married here recently, my partner and I had chance to explore the most stunning towns and cities, as well as hidden wineries and Insta-worthy spots in the countryside. All in the name of wedding research, of course. Here’s our pick of the most romantic things to do in Tuscany.

From Chianti’s sun-drenched vineyards to San Gimignano’s iconic towers – Tuscany is a romantic’s dream and the perfect place for living the simple Italian life. Even better, it’s easy to rent a car and take probably one of the most beautiful road trips of your life. The dusty, cypress-lined roads are part of the charm here.

There are 10 key provinces of Tuscany – Florence, Pisa, Lucca, Siena, Arezzo, Grossetto, Livorno, Massa Carrara, Pistoia and Prato. It stretches from Arezzo’s idyllic countryside to the coast where you’ll find scenic beaches and hiking trails aplenty, meaning there’s such a wide variety of things to do in Tuscany.

Wine lovers should head just south of Florence to the Chianti region, while the cities of Lucca and Siena are home to some of the best restaurants in Italy. Smaller towns like Montepulciano, Pienza and Certaldo are worth a visit on the way for the best gelaterias and local products – from red wine to cured meats.

The Val D’Orcia area is about as Tuscan as it gets, with the most picturesque valley setting and Tuscany’s most-photographed church, chapel Madonna di Vitaleta. And not forgetting, the beaches along the coast, including high-end Forte dei Marmi, iconic Porto Ercole and stunning Elba island. This is the place to live the dolce vita and from this romantic to you, here are our recommendations for the most unforgettable things to do.

Have you been to Tuscany? Where did you stay and where did you visit? If you had the trip of a lifetime let us know so we can add your favourite highlights to the list of the most romantic things to do in Tuscany below. Tell us about your experiences and let’s raise the profile of the places that are truly unforgettable. Contact us and let us know.

For more warm Tuscan hues and Italian elegance take a look at the stunning Rosewood Castiglion del Bosco. And for more romantic getaway ideas you might like our feature on these stylish overwater bungalows and our ultimate South of France road trip 7 day itinerary

Wild Bay Co is as much a celebration of the people who make these incredible experiences possible, as it is a celebration of the luxury resorts and hotels themselves. If you’ve stayed somewhere outstanding that deserves recognition for its exceptional attention to detail as well as its stunning setting then contact us and let us know.

This historic centre of San Gimignano is a UNESCO World Heritage Site – and easily one of the most stunning Tuscan towns to explore.

Catch golden hour at the towers

San Gimignano

Atmospheric streets

With atmospheric streets and towers that date back to the 11th century, just walking around San Gimignano is one of my favourite things to do in Tuscany. The town’s beauty is what drew us in part to our farmhouse wedding venue Fattoria di Larniano, just a 5-minute drive away.

Known as ‘the town of fine towers,’ standing in the square watching the sun dip as birds swoop overhead is truly incredible. Shops selling olive oil, wild boar salami and local wines stay open until late, so early evening is the best time to explore. Then be sure to book dinner at one of the family-owned Michelin-star restaurants – the refined Linfa or the more down to earth Cum Quibus, both with incredible tasting menus.

San Gimignano Tuscany

10 courses of pure heaven – and more than worth the hype.

Try the tasting menu at Gucci Osteria


Unforgettable dining

Top of the list of foodie things to do in Tuscany is the Gucci Osteria de Massimo Bottura in Florene. We headed to Florence straight after our wedding for a post-nuptial dinner and the menu completely blew us away. Though chef Karime Lopez heroes Italian food, the menu will take you all around the world – from Mexican-inspired purple corn tostadas to pillowy pork steamed buns, all the way back to the best tortellini with parmiganio reggiano cream.

The impeccable service also made the experience unforgettable, not to mention the decadent Gucci gift shop that stays open for post-dinner browsing. It was only a short walk back to our hotel, the Helvetia & Bristol, also located in the fashion district and a place famed for its old-world grandeur. Even if you don’t stay here, I’d recommend a Negroni nightcap on their street-side terrace.

Gucci Osteria food

Nothing short of an icon on the Tuscan coast, that comes with its own private beach.

Stay at the iconic Il Pellicano

Porto Ecole.

Tuscan icon

The Italian countryside never gets old, but if you want a taste of the coast, this is one of the best places to stay. Originally founded by two socialite lovers, Hotel Il Pellicano is a home-from-home for wealthy Italians and tourists. Think balconies draped with bougainvillea, calming lounge areas and a cocktail bar that’s open 24/7. There’s also a Michelin-star restaurant where you can tuck into refined Tuscan dishes under the stars.

By day, you can switch between the Slim Aarons-inspired pool and the beach club, set in one of Monte Argentario’s most stunning coves. We celebrated our first wedding anniversary here and will never forget the time we spent lazily wandering the rosemary-scented gardens and jumping from the rocks into the sea.

Il Pellicano luxury hotel

Sip Italy’s most awarded wine in an architecturally stunning winery.

Try wine tasting and lunch at Antinori winery


Lush vineyards

Antinori nel Chianto Classico is about 30km south of Florence, so it makes for the ideal day trip from there, or a stop on your Tuscan road trip. Last year, the winery was awarded first place in the World’s Best Vineyards and is home to Chianti’s most typical grape, Sangiovese. Not only does the wine taste amazing but the setting is out of this world. Rising from the rows of lush vineyards is a vast rust-coloured building, with huge spiral staircases leading to the rooftop gardens.

The building is made of entirely natural materials, inspired by the Antinori family’s long-standing connection to the land. It’s also one of the most breathtaking lunch spots. Located on the rooftop, Rinuccio 1180 (named after the forefather of the Antinori family), offers views of the Tuscan hillsides and the menu is typically Tuscan with silky duck ragout pasta and tender wild lamb. Add a wine flight, and you have one of the most romantic dining experiences in Tuscany.

Antinori Winery Tuscany

A hidden, creative haven between Florence and Pisa.

Go see classical Italian art in the Tuscan hills

Certaldo Alto

Pretty hilltop town

We discovered this pretty hilltop town by chance when trying to find somewhere to stop for lunch in the Val D’Elsa area. We were drawn in by the tiny gelateria, just as you walk up to the town’s medival walls, and then stayed longer to explore the beautiful art.

The Priori Palace facade is a must-see with its stone and glazed terracotta coats of arms, including some by the della Robbia workshop – a family of Florentine sculptors dating back to the 1500s. Nearby is the Museum of Sacred Art displaying works belonging to the churches of the surrounding area. Go in the middle of July for the infamous Mercantia Street Theatre Festival – it’s one of the most unique things to do in Tuscany.

Certaldo Alto

There’s nothing more romantic than truffle pasta and the rolling Tuscan vistas.

Tuck into pasta with the best Tuscan views at Le Vecchie Mura

San Gimignano

Stunning views

Tucked away in San Gimignano, Le Vecchie Mura restaurant has the best views in Tuscany. The iconic panoramic terrace is close by, where plenty of people pull up for a selfie with the softly rolling hills and olive groves as their backdrop. But, if you book a table on the terrace here, you’ll get these views all to yourself.

There’s nowhere better to tuck into a classic pasta dish – the truffle Carbonara is my favourite – and a glass of local red. Stop by for lunch if you’re exploring the town, or book in for dinner and take a seat as the sun sets, you won’t regret it.

View from Le Vecchie Mura Tuscany

A peaceful, romantic lookout across one of Tuscany’s most fascinating cities.

Climb Siena’s stunning Duomo


Romantic lookout

Siena is another beautiful city to get lost in. Quieter than Florence but no less charming, the winding streets and narrow cobble-stoned alleys are like a real-life maze. There are also some romantic lookout points to check out. Our favourite was the Facciatone – the high tower that’s part of the Duomo. It’s a stunning building in itself, but the tower offers the best views of the city including the Piazza Del Campo.

Go in July and August for the Palio di Siena Horseback Race – the square fills with thousands of spectators and the horses run around the edges of the grand Piazza del Campo.


Delicious, down-to-earth dishes – all under one stylish roof.

Eat like a Florentine at the Mercato Centrale


Amazing local food

Okay, so a bustling local food market might not sound like the most romantic spot but you’re guaranteed to fall in love with the dishes on offer here. From fresh pasta at Pasta Fresca to Luciano Savini’s fresh truffles, at first I was a bit overwhelmed by all this amazing local food, but it fast became our favourite spot in Florence.

We went here for lunch twice, as we wanted to try as much as possible, and with the Duomo so close by, it’s great for fuelling your climb to the infamous landmark. Or you can stop by for longer and try one of the cookery school courses together, it’s guaranteed to be one of the best foodie things to do in Tuscany.

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