Guide: Explore Tuscany

Nestled among endless vineyards and sun-drenched olive groves, discover the historic region of Tuscany, known for its powerful wines and charming medieval towns. With recommendations handpicked by our Italian colleagues, this guide leads you to the places they return to time after time, revealing local favourites beyond the well-known highlights. Read on to discover Italy’s best sandwich, beautiful hidden bathing spots and other local must-tries when visiting the region.

Where to stay
As one of the bigger regions in Italy, Tuscany has a lot to offer and it might seem daunting to decide where to stay. To help you on your way, we have selected a handful of charming towns and local areas that we love.

  • The Chianti area is for wine lovers, who would love to live side by side with endless rows of vines on their holiday. Visit the charming small towns of Gaiole, Radda and Castelnuovo Berardenga and stop in each of them for a nice stroll.

  • If you’re drawn to history, Siena is one of Tuscany’s most iconic cities – an UNESCO World Heritage Site celebrated for its remarkably preserved medieval center. Visit our beautiful holiday homes near Siena.

  • Lucca is another historic city that feels like a living museum, home to grand churches and beautifully preserved buildings. Wander through its winding old streets or take a walk along the iconic city wall that encircles the town.
    Explore our handpicked holiday homes in the area near Lucca.

  • Florence is a true haven for art lovers and food enthusiasts, with iconic art collections, bustling food markets and small, atmospheric restaurants throughout the city. Cross the Arno River and move away from the busiest streets, and you’ll reach the area where locals prefer to eat. Sounds tempting? Discover our holiday homes near Florence.

  • Volterra is a small hidden medieval town that is located on the top of a hillside. If you care to wander through narrow streets that weave between old stone houses, this is definitely worth a visit.

Where to eat
It’s no secret that Tuscany is considered one of Italy’s culinary heartlands, and the region offers far more extraordinary food experiences than any guide could hope to cover. We have selected some local favourites, and the rumour from our Italian hosts and colleagues is that these are the places Italians themselves return to again and again.

  • In Lucca, De Giulio is the perfect spot to sample authentic Tuscan dishes. Try beloved classics such as Tortelli al ragù, Tagliatelle al pesto or Patate alla salvia.
  • If you’re in need of a quick lunch in Lucca, De Felice is a must, especially for a taste of the local speciality Cecina.
  • Near Livorno, Il Romito is said to serve some of the very best Pasta alla vongole in all of Italy.
  • Close to Montaione, Casa Masi offers a warm and cozy dining atmosphere, where spaghetti is famously served in a wheel of parmesan.
  • For one of the best sandwiches made with local, seasonal ingredients, head to I Fratellini in Florence.
  • If you’re looking to cool down, try the fruit sorbet from Gelateria La Veneta in Lucca.
  • A visit to the historic butcher Macelleria Falorni, run by the same family for generations, is a true taste of Tuscan heritage. It’s especially known for its high-quality cured meats and regional specialities.
  • In Florence at Trattoria Cammillo, an intimate restaurant where you can savour fried zucchini blossoms - a local delicacy.
  • Vini e Vecchi Sapori is also a must-try when visiting Florence! They make the most delicious pasta.
  • Osteria di Fonterutoli is located in the historic Mazzei estate, known for their wine. You should try the Bistecca alla Fiorentina.
  • Ristoro di Lamole in Greve has one of the best panoramic views in the chianti area, and is perfect for sunset dining.
  • If you are looking for homemade pasta, you should visit the authentic Osteria Le Panzanelle in Radda.

What to do
Whether you love the outdoors, cultural sightseeing, or world-class wine tasting, here are our best recommendations for what to do in the region.

  • Although the region isn’t known as a typical bathing destination, we recommend three beautiful places to bathe in nature. The hidden beach near Cala Leone, the thermal baths at Saturnia Therme and the turquoise Elsa River near the city of Castelfiorentino.
  • Take a break from the buzz of the cities and spend a day on the trails. We recommend hiking routes near Castelnuovo di Garfagnana or exploring the protected regional park, Parco Naturale della Maremma, near Grosseto.
  • The Uffizi Gallery in Florence showcases works by masters such as Botticelli, Leonardo da Vinci and Michelangelo, while the Galleria dell’Accademia houses Michelangelo’s iconic David sculpture.
  • What is a holiday in Tuscany without wine tasting? Visit Lamole di Lamole Winery and enjoy a glass of Chianti Classico.
  • Go Vintage shopping in the small boutiques of Florence. We recommend Giratempo Vintage, ub_firenze, and Desii Vintage.

Where to wander
Sometimes the best thing on a holiday is to have no plans, and just see where the road takes you. Here are our best tips for where to wander and let the adventure unfold on its own.

  • Tuscany’s landscape is dotted with remarkable churches, and while these may not be hidden gems, they remain unmissable. We especially recommend the Cathedral in Florence, Siena’s striped Duomo with its 180-square-metre crypt, and the elegant San Martino Cathedral in Lucca.

  • Take a trip to Pietrasanta, a town renowned for its vibrant artist community. Explore its many galleries or wander the streets to discover the sculptures displayed throughout the city.

  • Gaiole in Chianti is an area rich with ancient castles. In particular we suggest visiting Castello di Brolio and Badia a Coltibuono. Both historic castles where you can visit the property and taste the wines produced in their wineries.

Isabella Maimburg
Written by Isabella MaimburgDecember 2025

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