The Best of Tuscany

Explore the Tuscan villages

Spread throughout the region are town centers, each with their own unique sites and styles.

Siena is the one of the largest cities in Tuscany and has a rich history from medieval wars to its well-known Palio di Siena (horse race), and you can visit sites such as the Cathedral, Piazzo del Campo, many shops and cafes along the cobblestone streets, and scenic viewpoints.

Further south in the Val d’Orcia region, be sure to visit Montalcino, Pienza, and Montepulciano—these towns are relatively close to each other, and the drive between them offers quintessential Tuscan views.

Further north, visit Lucca and Pisa. Lucca is quaint and has many shops and cafes, and Pisa is, of course, famous for the leaning tower of Pisa.

Visit Florence

Beyond the quaint villages, don’t miss a stop in Florence during your time in Tuscany. It’s possible to take a day trip from the Tuscan countryside, or to get the most out of all the history, art, and culture, I’d recommend staying at least two nights in Florence. Then you can fully explore the Duomo, Uffizi Galleries, Accademia Gallery, Boboli Gardens, shopping along Ponte Vecchio bridge, and all the amazing cuisine.

One of my favorite activities is catching the sunset from Piazza Michelangelo.

Wine tasting

There are countless vineyards across Tuscany, where you can tour the grounds or cellars and enjoy a wine tasting experience of Chianti, Montalcino, Montepulciano, or other local favorites.

One of my favorite spots is Enoteca Tenuta Argentiera, where the property overlooks both the Tuscan hills and the sea.

Some hotels actually have their own vineyards, such as Castelfalfi or Il Borro, so you don’t even need to leave the property for a wine tasting experience.

Horseback riding

Feel like you’re living in a movie horseback riding through Tuscany, taking in the scenic views.

Cooking classes

Learn from the best in a pasta-making or cooking class. Many are hosted in local chef’s homes, or on Tuscan farms, where you cook with local ingredients and then get to taste what you made in a delicious meal.

Bike riding

Especially in the Val d’Orcia region, you’ll notice bike riders who have come from near and far to bike the Tuscan hills. This activity is not for the faint of heart (and I definitely recommend some advanced training), but if you love mixing fitness into travel, this would be perfect for you.

Relax at the spa

Many hotels have extensive spas and pools overlooking the Tuscan views. Take time to relax and recharge. If you’re looking for a more natural experience, you can also try the hot springs at Bagni San Fillippo.

Shop

Tuscany is known for its leather products, so this is the perfect place to shop for purses, belts, and more. You can also have items custom-made and monogrammed at local shops. Beyond leather, also shop for jewelry, olive oil, soaps, and more.

Outside of Florence, you can visit the luxury outlet mall for high-end shopping at a discounted price.

Enjoy the beaches

One often overlooked aspect of Tuscany is the coast and beautiful beaches. Enjoy a beach day in Livorno, Fallonica, Castiglioncello, or San Vincenzo, or stay a few nights at a resort on the coast.

I stayed at the Sense Experience Resort for part of my recent visit to Tuscany and would highly recommend it for its private beach, onsite dining, plethora of activities, and spacious rooms.

• La Giostra (Florence): Arguably the most popular restaurant in Florence, and for good reason. The food and fresh pasta is incredible, the ambiance is serene yet vibrant, and the staff is incredibly welcoming. Definitely recommend making a reservation in advance. The burrata with fresh honey was one of my favorite dishes.

• Locanda Demetra (Montalcino): This farm and cooking school is set on a garden with amazing views of Val d’Orcia. You can take a cooking class here, or simply enjoy a meal. Every bite I took was better than the one before, and you can see where the ingredients are sourced... in a garden a few feet away from the restaurant.

• Palazzo Tiglio (San Pancrazio): Located at a small boutique hotel, this restaurant serves mouth-watering Italian dishes. It’s worth the drive up the windy hill—or even better, stay for a couple nights on-site to enjoy the entire property. The sommelier helped pair local Italian wines for each course of our meal, including dessert.

• Panini Toscana (Florence): This local sandwich shop in Florence has fresh breads, cheeses, meats, and spreads so you can customize your sandwich. Highly recommend the pesto spread.

• La Terraza Pool Bar (Florence): Located at the Grand Hotel Minerva, this rooftop terrace has light bites and cocktails with impressive views of the Duomo. Stop here for a sunset drink, or fill up for an entire dinner.

• Ristorante a San Vincenzo Il Sale (San Vincenzo): Located by the coast, this restaurant has panoramic views extending from Elba to Gorgona. The farm-to-table dining experience sources local ingredients for incredible dishes.

• Sette di Vino (Pienza): This enoteca is quite small, offering an intimate dining experience. Try local wines and enjoy the tapas-style food and locally made pecorino cheese.

• Campo Cedro (Siena): In the heart of Siena, this restaurant offers a modern take on traditional Tuscan dishes. Trendy yet understated ambiance with cuisine created by a Japanese chef.