Tuscany is the beating heart of Italy—a dreamy region where golden hills roll into vineyards, cypress trees line winding roads, and every meal feels like a celebration. Whether you’re chasing Renaissance art, sipping Chianti in sun-drenched vineyards, or exploring medieval villages perched on hilltops, Tuscany offers timeless magic. From Florence’s cultural treasures to the quiet charm of countryside towns, there’s something for every kind of traveler. If you’re looking for inspiration for your next European adventure, this list of the 10 best things to do in Tuscany is the perfect place to start. Ready to fall in love with Italy?
Editor’s Note: The majority of the towns below I explored with my Solo-ish tour with G Adventures!
10 Visit the Leaning Tower of Pisa
No trip to Tuscany is complete without snapping a photo with this iconic architectural marvel. The Leaning Tower of Pisa may be a tourist cliché, but it’s still undeniably impressive. Climb its 294 steps for a unique view over Piazza dei Miracoli.
Pisa is far more than its world-famous Leaning Tower. This charming Italian city offers a blend of Etruscan history, culture, and beauty that enchants every visitor. The Piazza dei Miracoli (“Square of Miracles”) is home to the iconic tower, the majestic Pisa Cathedral, the Baptistery, and the Camposanto Monumentale — each a masterpiece of Romanesque architecture. This quick detour is a must if you’re hitting the highlights of Tuscany.
9 Wander Through San Gimignano
San Gimignano, often called the “Medieval Manhattan,” is famous for its skyline of ancient towers and beautifully preserved walls. This UNESCO World Heritage Site offers charming cobblestone streets, artisan shops, and breathtaking views of the surrounding countryside.
Don’t leave without trying the award-winning local gelato at Gelateria Dondoli. The slower pace and timeless atmosphere here provide a welcome contrast to Tuscany’s bigger cities. A leisurely afternoon in San Gimignano is one of the best things to do in Tuscany, especially if you’re seeking romance and history.
8 Enjoy Pecorino Cheese in Pienza
Pienza is a gem of the Val d’Orcia and an absolute must for food lovers. The town is famous for its pecorino cheese—sharp, savory, and delicious in every form. Wander into small cheese shops and taste your way through aged wheels, soft spreads, and truffle-infused varieties. The views from Pienza’s city walls are stunning, especially at sunset. It’s the perfect place to enjoy a glass of wine and a plate of local cheese while gazing across golden hills. A delicious stop on your Tuscan adventure.
7 Tour the Vineyards of Chianti
Tuscany and wine are a match made in heaven, and Chianti is the region’s crown jewel. Home to some of Italy’s most famous wines, this area is dotted with picturesque vineyards and rustic estates offering tastings and tours. Learn about the winemaking process, stroll through sun-drenched rows of vines, and sample robust reds paired with local cheeses and olive oil. Booking a guided wine tour ensures you get the full experience. For wine lovers, this is easily one of the best things to do in Tuscany. This is the Tuscany you dream about.
6 Discover the Val d’Orcia Countryside
With its rolling hills, golden wheat fields, and endless vineyards, the Val d’Orcia looks like it was plucked from a postcard. Drive or cycle through this breathtaking region to visit charming towns like Pienza, Montalcino, and Montepulciano. This area offers the quintessential Tuscan landscape you’ve seen in films and photos. It’s especially stunning during the golden hour when the light washes over the hills. Bring your camera—every corner is a photo opp.
5 Eat at a Tuscan Farmhouse
Savor an unforgettable meal at a rustic farmhouse surrounded by rolling vineyards and olive groves. Take your seat at a long wooden table set al fresco, with bottles of robust local wine and baskets of fresh bread. Tuck into local favorites like handmade pasta, garden vegetables, and locally sourced meats—prepared with love and tradition. Between bites, soak in the warm embrace of the Tuscan sun.
4 Explore Montepulciano – Filming Site of Twilight
Montepulciano is a dramatic hilltop town known for its Vino Nobile and cinematic beauty. Fans of Twilight will recognize it as the filming location for New Moon’s Volturi scenes, but there’s much more to enjoy here. Stroll through charming streets and piazzas, sample Vino Nobile di Montepulciano in ancient cellars, and enjoy sweeping views of the surrounding countryside. In the heart of the village is Piazza Grande, situated at the highest point in town, where the 14th-century Palazzo Comunale stands, with a tower offering views of the surrounding countryside. This romantic and atmospheric town offers a perfect mix of film history, fine wine, and Tuscan charm.
3 Climb the Torre del Mangia in Siena
For one of the best views in all of Tuscany, head to Siena and climb the 14th-century Torre del Mangia. Located in the heart of Piazza del Campo, this slender tower stands over 300 feet tall. The climb is steep but rewarding—you’ll be treated to panoramic views of Siena’s rooftops, surrounding hills, and even the Duomo – a Gothic masterpiece adorned with intricate marble facades, black and white marble columns, frescoes by Pinturicchio, and works from Michelangelo and Donatello. . Afterward, linger in the square with a gelato and watch the world go by. It’s a perspective on Tuscany you won’t find anywhere else.
2 See the Sights in Charming Cortona
This charming hilltop town became famous thanks to Under the Tuscan Sun, but its magic goes far beyond Hollywood. Cortona offers sweeping views of honey-colored buildings with terracotta rooftops and the valley below, quaint alleyways, and a laid-back vibe that invites you to slow down and soak it all in.
Head to the lively Piazza della Repubblica for a coffee, explore the Museo dell’Accademia Etrusca for treasures of its past, or hike up to the Basilica of Santa Margherita for an unforgettable sunset. It’s one of Tuscany’s lesser-known treasures, ideal for travelers seeking peace, beauty, and authentic Italian charm.
1 Explore the Wonders of Florence
Florence is a living museum—home to Renaissance masterpieces, iconic architecture, and an atmosphere that oozes culture. Visit the Uffizi Gallery to see works by Botticelli, Michelangelo, and da Vinci.
Piazza del Duomo, also known as Cathedral Square, is the heart of Florence, containing some of the city’s major monuments. The Piazza has been a UNESCO World Heritage site since 1982. It’s a bustling cultural square dominated by the magnificent Basilica di Santa Maria del Fiore (aka “the Duomo”), designed by Filippo Brunelleschi. Construction began in 1296 and took almost 150 years to complete. The stunning dome dominates the Florence skyline and can be seen far and wide. This iconic square also includes the Baptistery and Giotto’s Campanile, a tower offering panoramic views of the city.
Don’t miss the Ponte Vecchio is a beloved symbol of Florence, attracting tourists and locals alike with its historical significance and charming atmosphere. It is the oldest bridge in Florence, with a history dating back to Roman times. The arched bridge, which stretches over the Arno Rive,r is the only bridge in Florence spared from the destruction of World War II during the Nazi retreat in August 1944. Legend has it that it was Hitler himself who decided to save the Ponte Vecchio because of its beauty and cultural heritage.
Florence is a cultural feast that will leave you awe-inspired, and it’s the perfect base for day trips to other Tuscan gems.
Conclusion
Tuscany is a place where beauty, flavor, and culture collide in the most unforgettable way. Whether it’s your first visit or your fifth, there’s always something new to discover. So what are you waiting for—when will your Tuscan adventure begin?
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About the Author
Patti Morrow
is a freelance travel writer and founder of the award-winning international blog Luggage and Lipstick and the southern travel blog Gone to Carolinas. TripAdvisor called her one of the “20 Baby Boomer Travel Bloggers Having More Fun Than Millennials” and she was named one of the “Top 35 Travel Blogs” in the world.
She is also the star of the upcoming TV series “Destination Takeover” which is scheduled to premiere in the next few months.
Patti is the author of the book “Girls Go Solo: Tips for Women Traveling Alone,” and has over 150 bylines in 40 print and online publications, including The Huffington Post, International Living Magazine, Washington Post Sunday Travel, Travel Girl, Travel Play Live Magazine, and Ladies Home Journal. She has traveled extensively through six continents looking for fabulous destinations, exotic beaches, and adventure activities for her Baby Boomer tribe.
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