Tuscany Tours in Winter
Planning for a trip to Tuscany during Winter? We offer 10+ tour packages to Tuscany departing in Winter that have 450+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Tuscany on your Winter holiday.
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10 Best Winter Tours in Tuscany
Join one of these handpicked Tuscany Winter tour packages, tailored to the season.
12% Off Today
Discover Europe’s most celebrated cities and landscapes with the "Europe Escape" city sightseeing tour—a 12-day adventure beginning and ending in Rome. This flagship trip invites experienced travelers and seniors to journey through seven countries, including the magic of Paris, the wonder of the Swiss Alps, and the romance of Tuscany.
Explore iconic sights such as the Eiffel Tower, Pisa’s Leaning Tower, the canals of Venice, and the vibrant streets of Amsterdam. The moderate pace allows you to soak in each destination, while seamless logistics ensure a stress-free experience.
What makes this package a favorite among travelers? It’s the perfect mix of classic highlights and authentic local experiences, all wrapped into one action-packed and memorable European journey.
12 days
USD 2,970fromUSD 2,605
Craving a taste of Italy’s most iconic UNESCO sites in just five days? The "Italy City Break" is your passport to a whirlwind of art, history, and vibrant culture. Starting from Rome, you’ll journey to the medieval town of Assisi—birthplace of St Francis—before heading to Florence, the city where the Renaissance began.
Wander through Florence’s architectural marvels, then continue north to explore the artistic treasures of Bologna, Padua, and the canals of Venice. The adventure doesn’t stop there; Tuscany’s world-renowned vineyards invite you for a final taste of la dolce vita before a return to Rome.
Tailored for young adults and seasoned travelers who appreciate efficient yet immersive sightseeing, this trip ensures you soak up Italy’s best in record time. The guided tour package includes essential highlights, expert insights, and a seamless travel experience.
USP: A curated route through Italy’s cultural heartlands, blending world heritage sites, culinary delights, and breathtaking scenery—making it a perfect short escape for those who want to experience Italy’s essence without compromise.
5 days
fromUSD 1,780
14% Off Today
From Amsterdam’s charming canals to the majestic Swiss Alps, the Europe Jewel trip is a two-week art and architecture tour that spans the best of both Western and Eastern Europe. This immersive group journey takes you through 10 countries, including the Czech Republic, Austria, Hungary, and more. Explore vibrant capitals like Vienna and Budapest, sample authentic Italian cuisine, and lose yourself in the historic ambiance of Prague and Bratislava. Travelers who relish a balance of sightseeing, cultural experiences, and natural wonders will love the diversity on offer. The tour’s unique highlight? A seamless blend of Western allure and Eastern intrigue, ensuring an unforgettable, all-encompassing European adventure.
14 days
USD 3,155fromUSD 2,715
9% Off Today
Northern Italy’s finest treasures await on the 'Italy’s Treasures: Art, Food & Wine of Italy' trip, a 12-day guided tour from Lake Maggiore to Venice. Experience a harmonious blend of natural beauty, culinary delights, and artistic heritage as you journey through Stresa, Cinque Terre, Tuscany, Florence, and Venice.
Relax by the tranquil Alpine Lakes, explore Cinque Terre’s medieval villages, and ride off-road vehicles through the marble quarries of Carrara. Enjoy a leisurely four-night stay at a Tuscan villa, where you’ll learn the secrets of Tuscan cuisine in a hands-on cooking class. Discover Florence’s Renaissance wonders and the enchanting canals of Venice.
The USP? The immersive culinary and cultural experiences—like cooking in a family-owned villa—set against the backdrop of Italy’s iconic art and landscapes, creating a tour that’s both indulgent and inspiring.
12 days
USD 4,349fromUSD 3,949
Create lasting memories with your children on the "Rome, Florence & Tuscany Family Adventure," a trip designed for families eager to bond over Italy’s treasures. Explore the myths of Roman emperors at the Colosseum, marvel at the Vatican’s masterpieces, and journey through Siena’s medieval streets en route to Florence.
In Florence, meet Michelangelo’s David, stroll Renaissance avenues, and soak in the magic of the Uffizi. The adventure continues through Tuscany’s iconic vineyards—perfect for parents and kids alike to discover the region’s timeless charm.
This private tour package balances immersive guided experiences with free exploration, ensuring flexible adventures for all ages. The unique selling point: fully customizable options to tailor your Italian journey to your family’s interests, making every day both educational and unforgettable.
8 days
fromUSD 7,712
From the medieval charm of Assisi to the artistic grandeur of Florence, the Discovery of Italy: 8 Days tour offers an easy-paced journey for young adults and seasoned travelers alike. Explore the Leaning Tower of Pisa, wander Bologna’s elegant streets, and soak in Venice’s romantic canals. The itinerary captures Tuscany’s rolling hills and Montepulciano’s beauty, with Rome bookending your adventure. The unique selling point: a curated blend of Italy’s top attractions and cultural encounters, ideal for those eager to uncover the best of Italy in a single trip.
8 days
fromUSD 2,750
Picture yourself winding through the Chianti hills, glass in hand, as you embark on the "Private Gourmet Wine Tour in Tuscany." This four-day easy-paced trip is designed for experienced travelers who appreciate the finer things in life. Savor world-renowned wines like Brunello di Montalcino and Chianti DOC, indulge in local delicacies, and explore the storybook villages of Volterra and San Gimignano. With private guidance and a flexible itinerary, this tour package blends scenic landscapes, culinary delights, and personalized attention. The USP? Exclusive access to authentic Tuscan experiences—perfect for those seeking both indulgence and cultural depth in their Italian getaway.
4 days
fromUSD 2,843
11% Off Today
Experience the essence of Europe on the Europe Highlights trip—a 10-day whirlwind journey through Rome, Paris, Lauterbrunnen, and beyond. This moderate-activity tour is tailored for experienced travelers and seniors eager to tick off iconic sights: marvel at the Eiffel Tower, cruise the Rhine, explore the Swiss Alps, and wander Venice’s canals. Indulge in regional cuisine, stunning scenery, and vibrant cultures across seven countries.
The tour’s unique selling point is its expertly crafted itinerary, delivering Europe’s most beloved attractions in a single, unforgettable trip—perfect for those who want to see it all with maximum ease and enjoyment.
10 days
USD 2,525fromUSD 2,235
This self-drive tour offers you the opportunity to discover one of the most beautiful areas in Italy: Tuscany. Visit at your own pace and choose how you want to spend your days. Begin your Tuscan adventure in Montecatini Terme, a charming spa town nestled in the Province of Pistoia, ideal for relaxing amidst thermal waters and elegant architecture. Next, you may decide to visit Lucca, just 30 minutes away, where ancient walls and Roman streets lead to San Michele’s majestic piazza. Then, continue to Pisa and marvel at the iconic Leaning Tower, Baptistery and Duomo in the stunning Piazza dei Miracoli. Later, explore Florence, home to Renaissance treasures like the Duomo, Michelangelo’s David, and the Uffizi Gallery. The following day, immerse yourself in the rolling vineyards of Chianti, savoring wines in Radda and Greve, with a detour to picturesque Montefioralle. Onward to Siena, wander medieval lanes to Piazza del Campo, then step back in time in San Gimignano, famed for its towers and timeless views. Conclude your stay with panoramic scenes from Montecatini’s historic funicular before heading south toward Rome. In Rome, explore iconic landmarks such as the Colosseum, Pantheon, and Trevi Fountain. Stroll historic streets, savor authentic Italian cuisine and reflect on a journey filled with culture, beauty and timeless charm. This route is perfect for those seeking Scenic tours of Italy, blending culture, relaxation and breathtaking countryside.
7 days
fromUSD 629
15% Off Today
COACH TOUR: Explore the best of central Italy on this five-day journey from Rome to Venice, with scenic stops in Florence, Bologna and the Tuscan countryside. Visit Assisi and Siena en route to Florence, where Renaissance treasures and Tuscan cuisine await. Wander Bologna’s historic streets and enjoy a street food tasting before heading to Venice for gondolas, cicchetti and grand architecture. Wrap up with wine and views in hilltop Montepulciano before returning to Rome. With guided sightseeing, regional flavours and iconic landmarks throughout, this compact adventure is perfect for travellers keen to experience Italy’s cultural heart in style.
5 days
USD 1,475fromUSD 1,254
See all Tuscany Winter Tours
Top Tuscany Tour Activities for Winter
From city sightseeing tours to art and architecture and others, here are some popular tour activities in Tuscany with departures in Winter.
Tuscany Winter Tours for all Age Groups
Tuscany tours in Winter designed for all ages—families, young adventurers, seniors, and everyone in between.
Trending Tuscany Winter Tour Deals
Popular Tuscany Winter multiday tours now available at reduced prices, on sale for a limited time.
12% Off Today
The Europe Escape tour is the flagship tour that started it all! Journey to 7 top countries in Europe on this 12-day Europe trip. Discover the magic of Paris and the French countryside. Journey to the heart of the Swiss Alps and grab your chance to see the Top of Europe! Explore Pisa, Rome, Florence and Venice and experience the Italian way of life. Enjoy the beauty of Austria and Germany before exploring the vibrant streets of Amsterdam. Our Europe Escape package remains a firm favourite with our travellers!
12 days
USD 2,970fromUSD 2,605
14% Off Today
Designed for passionate travellers, this 2-week Europe Jewel tour unveils the best of Western and Eastern Europe! Immerse yourself in Dutch culture in Amsterdam and cruise the scenic Rhine Valley in Germany. Explore historic cities like Nuremberg, Prague, and the Slovakian capital of Bratislava. Indulge in traditional Italian flavours, marvel at the natural beauty of the Swiss Alps, and discover Parisian delights. This guided group vacation promises an unforgettable European adventure!
14 days
USD 3,155fromUSD 2,715
9% Off Today
Vineyards, olive groves, and cities that float. Incredible history, indelible culture, and unforgettable cuisine. This is l’Italia at its most iconic. Enjoy the natural beauty and calm of the Alpine Lakes region. Snake along the edge of the sea to the medieval villages of Cinque Terre. Aboard off-road vehicles, explore the marble quarries of Carrara, where Michelangelo obtained the marble for his statue of David. Relax during a leisurely 4-night stay at a Tuscan villa. At a family-owned villa, learn the fine art of creating Tuscan cuisine during a hands-on cooking class. Explore Florence, the birthplace of the Renaissance. Discover Venice, a city of winding canals and bridges. From medieval masterpieces to bustling piazzas, be swept away by the legendary treasures of northern Italy.
12 days
USD 4,349fromUSD 3,949
11% Off Today
Embark on one of the most beloved European tours and see all the top attractions! The tour kicks off in Rome and explores Europe's highlights over 10 exciting days. Discover world-famous sights in France, Switzerland, Italy, Austria, Germany, the Netherlands and Belgium. Take advantage of the opportunity to tick the top attractions off your bucket list, from the Rhine River and the Swiss Alps to the Eiffel Tower and the Venice canals. Indulge in traditional meals, awe at the stunning natural scenery and experience the local culture. Are you ready for an unmissable, jam-packed European discovery?
10 days
USD 2,525fromUSD 2,235
7% Off Today
On a journey through the less-traveled country roads of Umbria and Tuscany, discover another side to the Italy you love. Stroll Assisi’s old city, and explore the Umbrian hill town of Spoleto, where the gilded façade of the cathedral rivals with the silvery sheen of the olive trees. Visit Florence, the “Cradle of the Renaissance.” In Siena, stand inside one of Tuscany’s most ancient piazzas. Admire the famous towers of San Gimignano and hunt for truffles in the Umbrian countryside. Delight in regional specialties and Italian wine with every dinner. Feel like a local as you discover the marvels of wine, cuisine, culture, and history.
11 days
USD 3,749fromUSD 3,499
15% Off Today
COACH TOUR: Take in the best of Italy on this 11-day journey from Rome, looping through Florence, Venice, and the sun-drenched south. Explore ancient ruins in Pompeii, cruise the canals of Venice, and marvel at the Vatican’s artistic treasures. Sip Tuscan wine in Montepulciano, discover Renaissance Florence, and see Pisa’s famous Leaning Tower. In the south, enjoy a formal dinner in Sorrento and a day trip to the glamorous island of Capri. With guided tours, scenic drives and plenty of local flavours, this trip blends history, culture and coastlines—perfect for anyone wanting a deep dive into Italy’s many highlights.
11 days
USD 3,455fromUSD 2,937
15% Off Today
COACH TOUR: Explore the best of central Italy on this five-day journey from Rome to Venice, with scenic stops in Florence, Bologna and the Tuscan countryside. Visit Assisi and Siena en route to Florence, where Renaissance treasures and Tuscan cuisine await. Wander Bologna’s historic streets and enjoy a street food tasting before heading to Venice for gondolas, cicchetti and grand architecture. Wrap up with wine and views in hilltop Montepulciano before returning to Rome. With guided sightseeing, regional flavours and iconic landmarks throughout, this compact adventure is perfect for travellers keen to experience Italy’s cultural heart in style.
5 days
USD 1,475fromUSD 1,254
13% Off Today
Are you keen for winter travel? Europe in winter is a wonderland! Starting in Amsterdam, admire the canal-side sights before travelling to the scenic German Rhine Valley and the historic city of Nuremberg. Enjoy a magical Christmas Day in the must-see city of Prague! Travel between Bratislava, Budapest, Vienna and Ljubljana. Get immersed in the Italian charms in Tuscany, toast the New Year in Switzerland and marvel at the festive atmosphere in Paris. What better way to spend Christmas than exploring enchanting Europe over two weeks?
14 days
USD 3,320fromUSD 2,885
10% Off Today
Venture along the glittering Mediterranean coast on an immersive journey connecting the Spanish, French and Italian Rivieras. Taste your way along the Mediterranean coast sampling traditional Catalan specialties in a 17th-century farmhouse, flavorful Provençal cuisine in Marseille, and traditional focaccia in Genoa. Enjoy the iconic must-sees and venture to gems off the beaten path, like the rolling hills of the Tuscan countryside. Take a step into the culture and meet the locals. From chameleonic Barcelona to sun-kissed Nice; from glamorous Monaco to the rolling hills of the Chianti countryside, find your dream Mediterranean journey.
16 days
USD 6,299fromUSD 5,699
20% Off Today
Tick off Europe’s top destinations on this Europe Christmas & New Year tour. See London's sights and cruise the Rhine River in Germany and Amsterdam's canals. Capture famous landmarks such as the Leaning Tower of Pisa and the Eiffel Tower. Spend Christmas Day in the snowy Swiss Alps and visit the medieval town of Bruges. Taste and toast your way through Europe this festive season, savouring local delights in each country. Enjoy lunch at a British pub, indulge in Bavarian delights, sample Tuscan cuisine and try traditional Belgium waffles!
14 days
USD 3,810fromUSD 3,038
Tuscany Winter Tour Types
Discover Tuscany Winter tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
Reviews of our Tuscany Tours for Winter
Feedback from guests whose tour started in/around Tuscany during Winter.
Elvie | Traveled in January
Excellent tour. Our tour leader Gustavo is excellent. He is amazing, friendly and helpful. Very accommodating. Gustavo makes all things possible. Very nice person. He showed us all the views and landmark of each country. Alex is an excellent driver. Very helpful and friendly. Overall this tour is amazing.
Barbara | Traveled in December
I have had the wonderful pleasure of touring with you, the tour was well executed. The experiences are amazing and very unique. So much fun and I will tour again. I will recommend.
Jordan | Traveled in December
Perfect group tour covering Italy. Well paced with plenty of activities balanced with good free time. Hotels, food, scenery, culture, history, fun, all great. Brilliant local tour guides and driver. Stayed at very comfortable and clean hotels with breakfasts included. On the whole a very enjoyable experience.
Russell White | Traveled in December
What a beautiful time spent in Tuscany on this trip. This was a wonderful tour. Great accommodations! Fabulous wines and meals. We had a wonderful driver, Brando, who was patient and knowledgeable. This is a trip well worth it. Villa Lecchi was elegant and made us feel very special! Spectacular location in the heart of Chianti hills
Sean E. | Traveled in December
The tour operator planned what would have been a very challenging itinerary to pull off solo, with probably a couple too many places to visit, and executed absolutely wonderfully. Seamless, low maintenance and highly helpful - be on time where asked, use the resources/insight from the tour guide, and make the most of your free time. Exploring Europe became that simple, leaving all other moments to absorb and experience. I've never so clearly remembered details from a vacation before. The operator is a great way to take the stress out of seeing a new place. Aaron, our tour guide, and Rocket, our coach driver, truly enhanced the experience with their knowledge, expert planning, humor and cameraderie. I'll definitely be traveling with Expat again in the hopefully not so distant future.
Anonymous | Traveled in January
This is our 8th cycling trip with this tour operator and one of the best. It has it all- great cycling on mainly quiet roads, but as others have said it would be best to do some hills before travelling so you can enjoy it. Wonderful scenery passing through lovely villages. Great food and wine - lets not forget the wine! I also enjoyed the coffee stops and gelato stops. Enough time was given to look around the places we passed through. Oh and great guides.
Get a customized trip to Tuscany in Winter
Plan a multi-country or regional adventure across Tuscany in Winter, with help from a local expert.
Alessandra GalassiTravel Expert in Italy
Danilo CataniaTravel Expert in Italy
Enrico Maria MalacarneTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
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