Tuscany Tours in Winter
Planning for a trip to Tuscany during Winter? We offer 10+ tour packages to Tuscany departing in Winter that have 140+ 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.
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
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
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
It’s the most wonderful time of the year on this 10-day Europe Highlights Christmas tour! This festive journey will take you from Italy to Switzerland and back again with countless adventures in between. Discover the beauty of Venice, Munich’s famous Christmas markets, the Amsterdam canals, the twinkling lights of Paris and the snowy Swiss Alps on Christmas day. Visit mountainous Innsbruck, explore the charming Belgian city of Ghent, cruise the Rhine River and admire Florence’s masterpieces. End the tour in Rome on New Year’s Eve after making memories to last a lifetime!
10 days
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
Venture off Italy’s beaten path and immerse yourself in the rustic heart of Umbria and Tuscany on this 11-day countryside and village trip. Starting in Rome and winding through enchanting towns like Spoleto, Assisi, Siena, and Florence, this tour is crafted for experienced travelers and seniors eager for a moderately active, culturally rich escape. Hunt for truffles with local experts, admire ancient piazzas, and sample the world-famous wines and regional cuisine that define this region. The journey’s highlight is the chance to live like a local—delighting in daily Italian specialties and savoring the slow pace of village life. The tour package’s unique selling point? Its focus on authentic experiences and lesser-known gems, offering a genuine taste of Italian tradition beyond the usual tourist trails.
11 days
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
Set off on a sun-drenched Mediterranean Coastal Journey from Barcelona to Tuscany, weaving through Spain, France, and Italy over 16 immersive days. This moderate-activity sightseeing tour is ideal for seniors and experienced travelers eager to sample regional flavors—paella in Barcelona, Provençal cuisine in Marseille, and focaccia in Genoa—while exploring iconic sites like La Sagrada Familia and the Tuscan hills. Go beyond the tourist trail by meeting locals and discovering hidden gems in glamorous Monaco and the Chianti countryside. The unique selling point: a carefully crafted journey connecting the best of three Mediterranean coasts, blending culinary delights with cultural insight.
16 days
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
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
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Top Tuscany Tour Activities for Winter
From art and architecture tours to cultural, religious and historic sites and others, here are some popular tour activities in Tuscany with departures in Winter.
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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
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
It’s the most wonderful time of the year on this 10-day Europe Highlights Christmas tour! This festive journey will take you from Italy to Switzerland and back again with countless adventures in between. Discover the beauty of Venice, Munich’s famous Christmas markets, the Amsterdam canals, the twinkling lights of Paris and the snowy Swiss Alps on Christmas day. Visit mountainous Innsbruck, explore the charming Belgian city of Ghent, cruise the Rhine River and admire Florence’s masterpieces. End the tour in Rome on New Year’s Eve after making memories to last a lifetime!
10 days
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
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
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
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
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Reviews of our Tuscany Tours for Winter
Feedback from guests whose tour started in/around Tuscany during Winter.
Maymay | Traveled in December
I really enjoyed traveling with Expat Explore in this Europe Highlights Tour. It was very organized and we didn't encounter any problem at all. Roma was a very knowledgeable and informative tour guide and she makes sure that we follow our schedule. Meanwhile Peter was a very skilled driver, he knows his way around (I don't think he use Google map or gps to get to places hahahaha). We really felt safe during the entire trip. We love the hotels that we stayed, they're clean and some of them are spacious. I will definitely recommend Expat Explore to my friends and family!
Ran | Traveled in January
The tour was fun. I really like it. Gustavo was really organized and very informative with our trips. He is very knowledgeable with the places we have been. Gustavo is a very responsible tour leader and he made sure everyone are safe. Also, Alex was a very professional driver. Amazing long travel and alex drove safely. We had 5 star treatment these two great people!
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
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