Top Tuscany Overnight Tours

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!

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.

Venture into Tuscany on this day trip from Florence and discover the region's highlights with the help of a local guide. 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 all-in-one package includes immersive audio experiences across six of the city's most iconic landmarks: the Florence Duomo, Accademia Gallery (home to Michelangelo’s David), Boboli Gardens, Ponte Vecchio, Santa Croce, and Piazzale Michelangelo. With over 40 expertly narrated chapters, you’ll unlock the stories behind the art, architecture, and legends that shaped Florence. Enjoy flexible, offline access and explore the city at your own pace—no schedules, no crowds, just pure discovery. Perfect for independent travelers, art lovers, and history enthusiasts seeking a deeper connection with Florence.

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.

Discover some of the highlights of Tuscany on this day trip from Florence by coach. Visit historical hill towns Pienza, Montalcino, and Montepulciano; admire the gorgeous, vineyard-covered scenery of Orcia Valley (Val d’Orcia); and enjoy cheese and wine tastings as you stop at local wineries and other venues. It’s a great day out in the Italian countryside.

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.

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.

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.

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.

Embark on a two-day adventure through Tuscany, starting with a visit to Montalcino, Montepulciano, and Pienza. Explore historic towns, enjoy Brunello and Nobile wine tastings, and take in stunning views of the Val D'Orcia. The second day continues with a journey to Siena, San Gimignano, and Chianti, featuring renowned wine estates like Casa Emma, where you’ll taste Chianti and Supertuscan wines. With a perfect blend of history, culture, and local wines, this trip offers a true taste of Tuscany.

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.

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.

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.

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

From the magical moment of your proposal to the unforgettable day you say “I do,” we are here to design an intimate and elegant journey through Tuscany and Florence. Every detail is curated with passion and refined style — from breathtaking venues and romantic atmospheres to exclusive touches that make your love story truly unique. A professional photographer will always be by your side, capturing the emotions, laughter, and timeless beauty of each moment with stunning images you’ll treasure forever. Whether it’s a secret proposal overlooking the Tuscan hills or a wedding celebration in a historic Villa with golden light at sunset, your experience will be as extraordinary as your love. Contact us to craft a tailor-made package designed around your wishes and budget, ensuring your dream becomes a reality.

A 2-day tour in the heart of Umbria between Assisi and Gubbio, two Italian pearls. 1 day departure from Tuscany and arrival in Assisi where we will visit the village and the famous Basilica of San Francesco. After he will take a walk through the center and in the afternoon we will move near Gubbio where the farm will welcome us with a fantastic tasting of typical products surrounded by greenery. On the second day we will visit the historic center of Gubbio with a personalized guided tour. In the afternoon, return to the hotel in Tuscany