8 must-see places in Tuscany

Ineke • Oct 5, 2023
Gourmet cuisine, world-class art, and scenic vistas — la dolce vita is calling, and it’s calling from Tuscany. Known for fine wines and medieval architecture, the region is the perfect place for rest and relaxation. Travel back in time to a world of traditional art, culture, and cuisine as you enjoy a backdrop of romantic, rolling vineyards and sunsets sure to stun.

What are the best places to visit in Tuscany?

1. Siena

Stretching across a Tuscan hilltop, Siena is Italy’s most picturesque medieval city. Leave the chaos of cars behind — these streets were made for strolling. Get lost in tumbling brick lanes and wind up at the cathedral: an over-the-top marvel of Gothic architecture lavished with mosaics and busts of 172 popes. A place frozen in time, Siena is the perfect refuge for travelers looking to escape the modern world for a day. Explore the city by foot on a walking tour or sample fine local wines. Between its looks and its famous grapes, Siena is an experience to savor.

2. Porto Ercole

Resting beyond ancient city gates, Porto Ercole is a place where pedestrians can stretch their legs and slather on some sunscreen. Head here to trade in the clamor of city life for the soothing serenade of seaside waves. Perfect for sunset strolls, this charming stone village fuses luxury with the old way of life. You’ll find artisans crafting traditional goods in converted fisherman's huts while extravagant yachts line the harbor and boat rentals give visitors the opportunity to explore the scenic coastline. Spend the day exploring one of the many “forte” or soaking up the sun at Feniglia Beach, while paying tribute to the passing of Baroque painter Caravaggio who died here in 1610 — a piece of history woven into the idyllic beach life.

3. Volterra

Famous for its peculiar urban layout, Volterra is a Tuscan town with deep roots, dating all the way to the 5th-century BC. Take a step back in time as soon as you stroll through the city gates, Porta dell'Arco and Porta Diana, and experience the ancient acropolis which houses the foundations of two ancient temples. And if its Roman ruins you’re after, look no further: Volterra is home to an amphitheater from the first century AD and features many workshops which maintain the tradition of alabaster handicrafts. Watch as this ancient town comes alive during a medieval reenactment in the summer months — the perfect occasion to enjoy Italian food and wine while the present transforms into the past.

4. Florence

The home of the Renaissance, Florence is the birthplace of the modern world and houses some of Europe’s finest pieces of art including masterful oil paintings, stunning marble statues, and meticulous mosaics. In a single afternoon, you could experience the pensive stare of Michelangelo’s David, get a feel for the first day of spring with Botticelli's Primavera, and refresh yourself next to the fountain of Neptune. Of course, there’s a world to experience off the beaten path, so let your eyes wander to the food, fashion, and street markets that are renowned the world over — and don’t forget the gelato!

5. Talamone

Looking for an authentic Italian vacation? Talamone trades the hustle and bustle of city streets, crowded museums, and overbooked restaurants for an experience rich with scenic views and genuine Tuscan tradition. Once a fortified fishing village, the town retains its historic charm with winding, narrow streets, 13th-century architecture, and terracotta rooftops reaching the active harbor of the Tyrrhenian Sea. Only a three-hour train ride from Rome, this charming seaside town offers the finer things of the Mediterranean alongside the calm and serenity of small-town living — an appetite for seafood comes highly recommended.

6. Colle di Val d’Elsa

A town nestled between scenic hilltops and the rolling river Elsa, Colle di Val d’Elsa takes a few steps back in history with a rich tradition of art and culture at its core. Also known as “Città di Cristallo” or “City of Crystal,” the quaint village is famous for its production of crystal artifacts, dedicating an entire museum to the sought-after local crafts and featuring open-air glass blowing demonstrations to captive audiences in the city center. Wowing onlookers with its precious beauty, Colle di Val d’Elsa is the perfect destination for a truly Tuscan experience.

7. Monteriggioni

The most notable walled medieval location in Tuscany, Monteriggioni is a fortified village that began as a castle in the Chianti region, sitting atop a rounded hill for the past 800 years. Since the 1200s, onlookers have marveled at the mighty towers that surround the location from miles away, the same lofty towers which Dante compared to horrific giants in his Divine Comedy. Enjoy the fruits of the region with a wine tasting and explore the rolling hills of the Tuscan countryside. Oh, and have a camera handy: there are vineyards and cypress trees as far as the eye can see.

8. San Gimignano

As one of the best preserved medieval Italian hilltop towns, San Gimignano is considered a UNESCO World Heritage site famous for the Hundred Towers built in the Middle Ages by Italy’s most influential families. Rife with splendid squares, palaces, churches, and magnificent towers, San Gimignano calls Chianti its home. This breathtaking landscape is rich with green rolling hills, wide vineyards, and olive groves. But don’t take it from us — discover and savor the region on a Tuscan wine tour.