Top Tuscany Overnight Tours

Skip the hassle of renting a car and explore Tuscany on a day trip from Florence. Explore the medieval city of Siena and its cathedral before heading to the hills of Chianti for a Tuscan lunch and wine tasting (optional). Roam the streets of San Gimignano and travel to Pisa to admire the architectural drama of Cathedral Square—home to the UNESCO-listed Leaning Tower of Pisa. Upgrade to include admission to climb the tower.

This is the tour of the oldest Etruscan and Roman Maremma but remained intact over time. The thermal and healing spring attracts users from all over the world. Here you can breathe authenticity, history and rurality. Breathtaking views. Spectacular wines. The villages we will visit preserve the characteristics of Tuscany and its inhabitants still speak the ancient dialects. The Biodynamic, Biological company where we will have a picnic is truly an example of obsessive attention to traditions in respect of Nature! From the above you can enjoy a 360 degree view. Your basket includes: 2 basic wines, typical breads, 2 types of cheese, award-winning oil!

Navigate through the picturesque landscapes of Tuscany with the Tootbus Tuscany Multi-Day Pass. Enjoy unlimited travel across Florence, Pisa, Siena, Lucca, and San Gimignano, allowing you to explore at your own pace. This flexible pass eliminates the stress of rigid schedules, offering scenic routes through the stunning Chianti countryside. With Tootie, your AI-powered guide, receive personalized recommendations and real-time travel tips in over 50 languages, making your journey seamless and enriching. Start your adventure from any city at any time and immerse yourself in the beauty and culture of Tuscany.

Tuscany’s stunning Chianti hills are ideal for cycling, but navigating the winding country roads on your own is tiresome. On this two-day e-bike tour, follow your guide to discover charming villages, pass by rolling vineyards, and savor authentic Tuscan cuisine without the hassle of a map. Explore the towns of Mercatale and Impruneta, renowned for their terracotta production, while experiencing Tuscany's beauty and rich traditions. Perfect for those seeking a blend of adventure, relaxation, and luxury in one unforgettable trip.

Why choose between the coast and the countryside when you can have both? Our Combo 2-Day Tour lets you experience two of Italy’s most breathtaking regions—Pisa & Cinque Terre and Tuscany’s Chianti & San Gimignano—in one seamless adventure. Enjoy a stress-free experience with all logistics handled by a trusted team. On day one, explore the stunning seaside villages of Cinque Terre and admire the iconic Leaning Tower of Pisa. On day two, immerse yourself in Tuscany’s rolling vineyards, indulge in wine tastings, and discover the medieval charm of San Gimignano. With expert guides, comfortable transportation, and perfectly curated experiences, you’ll see Italy at its best—without the hassle. Make the most of your time and tick off two must-visit destinations effortlessly!

See what Tuscany has to offer without breaking the bank on this budget-friendly day trip to the region's highlights from Florence. Save hours with coach transportation and enjoy free time to explore the medieval old towns of Siena and San Gimignano, plus the sights of Pisa. Upgrade to a guided tour of Siena, or add-on a 2-course lunch with wine pairing for a hassle-free, all-inclusive day.

Dedicate two separate sightseeing days to explore Florence and Tuscany with a private local guide. A great option for those who want to explore freely without the strict timetables or restrictions of big group tours, this private sightseeing experience offers a loose itinerary that be customized with ease. Explore Florence by foot on the first day, and then meet your guide and driver the next day to discover some highlights of Tuscany.

Leave the bustle of Florence behind and escape into the peaceful landscapes of the Tuscan countryside. This exclusive two-day experience is designed as a true getaway from the city, where rolling hills, vineyards and medieval villages set the scene for a journey focused on food, wine and authentic local traditions. From the iconic towers of San Gimignano to the quiet beauty of the Chianti hills, you immerse yourself in Tuscany at a slower pace. Taste award-winning gelato, hunt for truffles in the countryside and enjoy a hands-on cooking experience using fresh local ingredients. Perfect for travellers seeking a short yet meaningful escape, this journey combines relaxation, discovery and unforgettable flavours in one of Italy’s most iconic regions.

Knowing where to visit in the Tuscan countryside can be daunting for first-timers, especially if you're starting off in Florence. Simplify your day out with this group tour. Once you've boarded your coach, sit back knowing the transportation and activities are covered, meaning you can fully immerse yourself in the experience. Enjoy visiting Pienza, Montalcino, and Montepulciano, the Orcia Valley, and taking part in a wine and cheese tasting.

Tick off several of Tuscany's most renowned locations during this full-day Vespa tour. Enjoy some photo stops in the vineyards and take a guided stroll through the picture-perfect village of San Gimignano, with free time to explore. The tour includes a typical Tuscan light lunch paired with a tasting of some local wines and olive oils.

Live 2 days in the Tuscan countryside near Montepulciano among vineyards, hills and breathtaking views. The experience includes e-bike tours and horseback riding through the dirt roads, visit to a winery with local wine tasting and time on the farm with typical Tuscan lunch prepared with local products. An authentic immersion in the real Tuscany, away from mass tourism.

Leave the busy streets of Florence behind and soak up Tuscany's views on this small-group Vespa tour. Hop onto your scooter once you reach the beautiful country roads of Chianti, so you don't have to navigate inner-city traffic. Stop for a traditional Tuscan meal at a farmhouse and taste olive oils and Chianti wines for an authentic taste of Florence's culinary scene. You can also enjoy the journey in a Fiat Topolino e-car.

Beginning from Florence, you will depart from the main train Station of Santa Maria Novella. After 1 hour you will reach Pisa Station before meeting your guide for a group tour of the main Square, Piazza dei Miracoli. This of one of the most important historical complex in Europe and has been a UNESCO world heritage site since 1989. The itinerary includes an introduction to the Square and of all its monuments (Baptistry, Monumental Cemetery, Leaning Tower and Cathedral) and a visit inside the Cathedral. With this tour you have the possibility to book tickets for the Leaning Tower in advance (Feel free to contact us for more information). After the visit you will have free time to walk by yourself in the city center, before choosing any train to get back to Florence

Escape the everyday and discover the timeless charm of Palazzo del Borgo, a beautifully preserved 16th-century residence in the picturesque village of Marradi. The palace offers an authentic Tuscan experience surrounded by historic elegance and a peaceful private garden. Your romantic getaway includes an overnight stay in an elegant Junior Suite. Enjoy a hands-on Tuscan cooking class led by local hosts, learning traditional recipes passed down through generations. Afterwards, unwind with an aperitivo featuring local wines and delicacies, followed by a romantic dinner celebrating the finest seasonal flavours of Tuscany. The next morning, wake up to a generous breakfast with homemade cakes, pastries, and local specialties. To make your stay even more memorable, choose from a selection of optional experiences, including a yoga session in the woods, a scenic hike with gourmet picnic, or a relaxing wellness moment with massage, manicure, herbal teas, and a glass of wine.

La Gallinella’s Ecolodges are nestled among picturesque chestnut woods, olive groves, cherry orchards and other breathtaking vantages throughout the 4-hectare grounds. All Ecolodges are furnished with an en-suite bathroom, a private kitchen, beds, and other amenities for a truly relaxing glamping experience. Take a stroll in the tranquil shade of La Gallinella’s forested footpaths and listen to the sounds of the lush, Tuscan countryside. Walk among the idyllic olive groves and cherry orchards. Or simply sit back, relax, and enjoy a cold beverage in the comfort of your Ecolodge—at La Gallinella, reconnecting with nature has never been more glamorous. If you’re interested in exploring the surrounding areas, there is no shortage of outdoor activities to enjoy. Horseback riding, biking, hiking, and sailing are a few popular pastimes for locals of the area. Some of Italy’s most beautiful natural spas are only a few miles away.