Tuscany Day Trip from Rome: The Perfect Guide

Tuscan destinations

Florence

Florence, the heart of the Renaissance, is a city rich in history and art. Start your visit at the iconic Cathedral of Santa Maria del Fiore, known as the Duomo, with its stunning dome designed by Brunelleschi. The Uffizi Gallery is a must-visit for art lovers, housing masterpieces by Michelangelo, Leonardo da Vinci and Botticelli. Don’t miss the Ponte Vecchio, a medieval stone bridge lined with jewelry shops. For an insider tip, visit the Boboli Gardens behind Pitti Palace for a peaceful retreat with fantastic city views. Florence’s compact city center makes it easy to explore on foot.

Pisa's Leaning Tower

The Leaning Tower of Pisa is one of Italy’s most famous landmarks. Located in the Piazza dei Miracoli, the tower’s unintended tilt has made it a must-see attraction. Climb the 294 steps to the top for a unique view of the city. Book a guided tour of Pisa and the tower from Florence for ultimate simplicity. While in Pisa, explore the Cathedral and Baptistery, both architectural marvels. For a less crowded experience, visit early in the morning or late afternoon. Don’t forget to take the classic “holding up the tower” photo, a fun and iconic souvenir of your trip.

San Gimignano

Known as the "Medieval Manhattan," San Gimignano’s skyline is dotted with ancient towers. Wander through its well-preserved medieval streets and visit the Collegiata di Santa Maria Assunta, a beautiful Romanesque church. The town is famous for its Vernaccia di San Gimignano wine, so be sure to stop by a local winery for a tasting. Insider tip: Climb the Torre Grossa for panoramic views of the surrounding countryside. San Gimignano is also renowned for its gelato, with Gelateria Dondoli frequently winning awards for its delicious flavors. For an exclusive experience, book a private wine and olive oil tasting.

Siena

Siena’s well-preserved Gothic architecture makes it a captivating destination. Visit the Siena Cathedral, a stunning example of Italian Romanesque-Gothic architecture, and explore the Piazza del Campo, the heart of the city and the site of the famous Palio horse race. The Palazzo Pubblico and its Torre del Mangia offer breathtaking views of the city. For a unique experience, visit during the Palio, held twice a year in July and August, to witness this thrilling event. Siena’s narrow streets are filled with charming shops and cafes, perfect for leisurely exploration.

Chianti Wine Region

The Chianti region is synonymous with wine. Embark on a scenic drive through rolling hills and vineyards, stopping at local wineries for tastings. The Chianti Classico Wine Route offers numerous opportunities to sample world-renowned wines. Visit Castello di Brolio, one of the oldest wineries, and enjoy a guided tour of its vineyards and cellars. Insider tip: Plan your visit during the grape harvest season in late September to early October for a chance to participate in grape picking. Pair your wine tasting with traditional Tuscan cuisine at a local trattoria.

Montepulciano

Montepulciano is famed for its Vino Nobile wine and stunning Renaissance architecture. Begin your visit at the Piazza Grande, the town’s central square, surrounded by historic buildings like the Palazzo Comunale. Tour the ancient wine cellars carved into the rock beneath the city, such as those at Cantina Contucci. For wine enthusiasts, a visit to a local winery like Avignonesi is a must. Don’t miss the chance to taste pici pasta, a local specialty. Insider tip: Visit the Temple of San Biagio just outside the town for its beautiful architecture and serene setting.

Val d'Orcia

The Val d'Orcia is a UNESCO World Heritage site renowned for its stunning landscapes. Take a leisurely drive through the rolling hills, stopping at picturesque towns like Pienza and Montalcino. Pienza is known for its pecorino cheese, and a visit to a local cheese shop is a must. In Montalcino, sample the famous Brunello di Montalcino wine. For an unforgettable experience, hike through the Crete Senesi, a unique clay landscape south of Siena. Insider tip: The Cappella della Madonna di Vitaleta, a small chapel set amid rolling fields, offers a perfect photo opportunity.

Lucca

Lucca is a charming city known for its Renaissance walls. Rent a bike and cycle around the tree-lined ramparts for a unique perspective of the city. The Piazza dell'Anfiteatro, a former Roman amphitheater, is now a bustling square with cafes and shops. Visit the Lucca Cathedral and the Church of San Michele in Foro for their beautiful architecture. Insider tip: Climb the Guinigi Tower, topped with oak trees, for panoramic views of Lucca. The city’s historic center is filled with delightful shops selling local crafts and foods.

Cortona

Made famous by the book and movie "Under the Tuscan Sun," Cortona offers stunning views over the Valdichiana. Visit the Piazza della Repubblica, the heart of the town, and the Diocesan Museum, home to works by Fra Angelico. The Church of Santa Margherita and the Eremo Le Celle hermitage offer peaceful retreats. Cortona’s steep streets are lined with charming shops and cafes. Insider tip: For the best views, hike up to the Fortress of Girifalco. Cortona’s vibrant cultural scene includes festivals and events throughout the year, such as the Cortona Mix Festival.

Hot Springs in Saturnia

Relax in the natural thermal baths of Saturnia, located in the Maremma region. The Cascate del Mulino are free, public hot springs with cascading waterfalls and natural pools. The water maintains a constant temperature of around 37.5°C (99.5°F), making it perfect for a soothing soak year-round. Insider tip: Visit early in the morning or late in the evening to avoid crowds and enjoy a more peaceful experience. The nearby town of Saturnia offers additional spa facilities and charming accommodations for those wishing to extend their stay.

Day Trips

If you have more time to explore, consider extending your journey beyond Tuscany with a visit to Umbria. This region offers a wealth of cultural, historical and natural attractions that are perfect for a day trip.

Perugia

• Historic Center: Perugia’s medieval center is filled with history and charm. Wander through Piazza IV Novembre, home to the Fontana Maggiore and the Cathedral of San Lorenzo.

• National Gallery of Umbria: Located in the Palazzo dei Priori, this museum houses an impressive collection of Umbrian art, including works by Perugino.

• Chocolate Lovers: Perugia is famous for its chocolate, and a visit to the Perugina Chocolate Factory is a must. Enjoy a factory tour and indulge in some delicious samples. Insider Tip: Visit during the Umbria Jazz Festival in July or the Eurochocolate Festival in October for a unique cultural experience.

Assisi

• Basilica of St. Francis: This UNESCO World Heritage site is a major pilgrimage destination. The basilica’s upper and lower churches are adorned with frescoes by Giotto and Cimabue.

• Rocca Maggiore: Explore this medieval fortress for panoramic views of Assisi and the surrounding countryside.

• Santa Maria degli Angeli: Just outside Assisi, this basilica houses the Porziuncola, the small chapel where St. Francis founded the Franciscan order.

• Insider Tip: Assisi can be crowded with tourists, so consider visiting early in the morning or late in the afternoon to enjoy a quieter experience.

Orvieto

• Orvieto Cathedral: One of Italy’s most beautiful cathedrals, known for its stunning facade and the Chapel of San Brizio frescoes by Luca Signorelli.

• Orvieto Underground: Take a guided tour of the underground tunnels and caves that have been used since Etruscan times.

• St. Patrick’s Well: An engineering marvel, this well was built in the 16th century to protect water supply during sieges.

• Insider Tip: Try the local white wine, Orvieto Classico, at one of the city’s many enotecas.

Civita di Bagnoregio

• The Dying City: This small village is perched on a hilltop and accessible only by a pedestrian bridge. Its unique location and stunning views make it a must-visit.

• Historic Walk: Explore the ancient streets and buildings, many of which date back to the medieval period. Insider Tip: Visit early in the morning or late in the afternoon to avoid the crowds and experience the town’s serene atmosphere.

Todi

• Piazza del Popolo: Todi’s main square is one of Italy’s most beautiful, surrounded by medieval and Renaissance buildings.

• Santa Maria della Consolazione: A Renaissance church with a striking circular design, attributed to Bramante.

• Todi Underground: Discover the city’s hidden history with a tour of its underground cisterns and tunnels. Insider Tip: Todi is known for its slow food movement. Enjoy a meal at a local osteria to taste traditional Umbrian cuisine.

• Osteria dell'Enoteca (Florence) Authentic Tuscan dishes with a focus on seasonal ingredients.

• La Taverna di San Giuseppe (Siena) Traditional Tuscan fare in a cozy setting.

• Antica Trattoria da Tito (Florence) Famous for its Florentine steak.

• Ristorante La Grotta (Montepulciano) Fine dining with a view of the Tuscan countryside.

• Cantinetta Antinori (Florence) Great selection of wines in a historic setting.

• Ristorante Nello (Florence) A local favorite known for its pasta dishes.

• La Bottega del Buon Caffè (Florence) Michelin-starred dining, offering an innovative take on Tuscan cuisine.

• Osteria Le Logge (Siena) Cozy ambiance and a menu featuring local specialties.

• Bar La Terrazza del Chiostro (Pienza) Stunning views paired with delicious food.

• Enoteca Pitti Gola e Cantina (Florence) A wine bar with expert pairings and a warm atmosphere.