Where to Go Tuscany: Insider’s Guide to Must-Visit Destinations!

Tuscany is worldwide famous for its fine wines, the medieval villages surrounded by cypress trees and olives groves, looking like coming out of a painting and of course some famous Tuscany cities to visit, like the capital, Florence, Siena, Volterra and San Gimignano.

However, there are many more places to visit in Tuscany. Off the beaten path villages and beachfront spots that offer you top experiences. The Tuscan countryside is ideal to relax, connect with nature, hike or bike along scenic routes and explore the wine-tasting options it offers you.

Tuscany Villas for Rent Villa Borghese
Villa Borghese Montevettolini Tuscany

Let’s see where to go in Tuscany if you want to explore its hidden gems away from the crowds. If you have already seen the best-known locations and you want to discover something different you have never seen before, these are the most beautiful places in Tuscany for demanding travelers.

Val d’ Orcia: The UNESCO World Heritage Site

Tuscany Villas for Rent Villa Palazzetta
Villa Palazzetta Montalcino Val d’Orcia Tuscany

If you wonder what is the most beautiful part of Tuscany, then definitely is Val d’ Orcia, although the choice is quite difficult. Val d’ Orcia is a wide region, which is included among the best places to go in Tuscany because of its unparalleled natural beauty and the numerous small or bigger villages with Italian-style architecture, colorful houses and medieval churches at stunning squares, where the old meets the new.

The road trip in Val d’ Orcia is something unique. As you drive from one village to the other, you will admire the elegance that characterizes the whole area. Cypress trees surround the well-preserved dreamy properties and villas that mirror the magnificence of this blessed land, while the olive groves and the vineyards give the place a full Mediterranean atmosphere.

The top villages you should visit in Val d’ Orcia are:

  • Pienza: Pienza is renowned for its Renaissance architecture and delicious pecorino cheese. The ideal walk is to stroll around its charming streets, visit the stunning Piazza Pio II and then take amazing photos with the breathtaking view of the valley from the town walls.
  • Monticchiello: A tiny village on a hilltop, Monticchiello gives you the opportunity to understand what traditional Tuscan life is. It has not so many shops and tourists and it is more authentic than other villages. There, you will admire the medieval houses with flowers on their balconies and taste authentic Tuscan cuisine in one of the local trattorias.
  • Bagno Vignoni: Bagno Vignoni is famous for its thermal baths that are located in the middle of the village, creating an impressive square. The healing waters of the Roman pool are surrounded by centuries-old buildings and serene countryside.
  • San Quirico: A village that only a few know, San Quirico is situated near Bagno Vignoni and is the ideal place to get rest during your road trip in Val d’ Orcia. It has a main pedestrian road that leads to an impressive Renaissance church, which you can admire while drinking your espresso in one of the lovely cafes.
  • Montalcino: A medieval village that is definitely worth visiting not only for its mystical atmosphere but also because it is famous for its DPO wine, Brunello di Montalcino. There are numerous wineries in a close distance, where you can learn about the wine-making process and taste the finest wines.


Val d’ Elsa: A less known but equally beautiful valley

Tuscany Villas for Rent Casale San Giovanni
Casale San Giovanni Casole d’Elsa Siena Tuscany

Val d’ Orcia is not the only place that reflects the best of Toscany. Val d’ Elsa near Siena is also one of the best places to visit in Tuscany, especially if you want to explore its authentic side. There are two settlements that we recommend you if you want to go off the beaten track:

  • Colle di Val d’Elsa: Often overshadowed by its more famous neighbors, Colle di Val d’ Elsa is a hidden gem waiting to be discovered. Explore its well-preserved medieval center, marvel at the craftsmanship of its crystal production and relax in the peaceful atmosphere of this lesser-known town.
  • Monteriggioni: Step back in time as you wander through the walls of Monteriggioni, a perfectly preserved medieval fortress at the top of the hill, overlooking the whole Val d’ Elsa. The village is very small, but it has many lovely shops and cafes, where you can sit and forget about the outside world.


Chianti: The homeland of famous wines

Tuscany Villas for Rent Villa Il Cellese
Villa Il Cellese Castellina In Chianti Tuscany

Chianti is a whole area, full of vineyards and wineries that produce some of the finest wines in the world. Castellina in Chianti is the best-known village, which takes its name from its castle-like setting.

However, you should also not miss Greve in Chianti and Radda in Chianti.

  • Greve in Chianti: Known as the gateway to the Chianti wine region, Greve is a charming village surrounded by vineyards and olive groves. It offers you the perfect opportunity to enjoy tasteful wine in a local trattoria and discover the charming atmosphere of this unique place.
  • Radda in Chianti: Located in the heart of the Chianti Classico region, Radda is full of medieval charm and rural tranquility. Its labyrinth-like streets, the hidden wine cellars and the panoramic views of the vineyard-covered hills make this small villages one of the best places in Tuscany.


The coastal beauty of Livorno

Tuscany Villas for Rent Villa Campolecciano
Villa Campolecciano Castiglioncello Maremma Tuscany

Are you wondering what to visit in Tuscany if you want to discover its coasts? Livorno is the port at the west side of Tuscany, combining the rural tranquility of Tuscan countryside with the enchanting essence of the sea.

In Livorno, we recommend you taking a stroll along the Terrazza Mascagni, a scenic promenade overlooking the sea and then explore the historic district of Venezia Nuova, known for its charming canals and colorful buildings. Worth visiting is also the Fortezza Vecchia, an ancient fortress with stunning views of the coastline. 

Castiglioncello is Tuscany’s best-kept secret, a coastal town with stunning beaches where you can live the sea life at its fullest. 

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Kinglike, the driving force behind this boutique luxury travel agency, brings a deep-rooted real estate expertise to curate exceptional villa rentals in Greece and Italy, with personal concierge services in Mykonos, Paros, Antiparos, and Tuscany. Each villa property reflects their personal admiration, ensuring guests a one-stop-shop experience that meticulously tends to every detail of their villa vacation. Read more about Kinglike

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