Italy Tours in Winter
Planning for a trip to Italy during Winter? We offer 190+ tour packages to Italy departing in Winter that have 3400+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Italy on your Winter holiday.
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10 Best Italy December Deals
December Deals exclusive deals on Italy Winter tours — limited-time massive savings on premium travel packages!
Curated by Alessandra Galassi
Italy travel expert at Bookmundi
Our 5-Day Tour offers a perfect blend of history, culture, and natural beauty. Start by exploring the vibrant streets of Naples before embarking on a scenic day trip to the stunning towns of Sorrento, Positano, and Amalfi. The next day, hop on a ferry to the beautiful island of Capri, where you can wander through charming streets, enjoy panoramic views from Augustus Gardens, and see the iconic Faraglioni rocks. Finally, step back in time with a guided tour of Pompeii’s ancient ruins, uncovering the fascinating history of this Roman city. With expert guides, unforgettable sights, and plenty of free time to explore, this tour is the perfect Italian getaway.
5 days
Dive headfirst into Europe’s greatest hits with the European Escapade—a 24-day whirlwind tour that starts and ends in London. From Amsterdam’s canals to the romance of Paris, the energy of Berlin, and the sun-soaked streets of Barcelona, this trip packs in legendary cities, Swiss Alps adventures, and exclusive Special Stays at Hopfgarten and Contiki’s Château de Cruix.
Tailored for young adults, this group tour delivers big on iconic sights, lively social scenes, and memorable moments. Upgrade to the ‘Plus’ for twin-share hotel comfort instead of the classic multi-share.
USP: An expertly curated city sightseeing tour package designed for those who want maximum Europe in minimum time—plus the perks of exclusive accommodations and unforgettable group experiences.
24 days
Experience authentic Italian living on the "Local Living Italy—Sorrento" trip, a seven-day trekking and hiking adventure based in the enchanting town of Sorrento. Perfect for travelers who yearn to go beyond surface sightseeing, this guided tour immerses you in the rhythms of daily life along the Amalfi Coast.
Your journey begins and ends in Naples, with highlights including coastal walks, an excursion to the fashionable island of Capri, and a guided visit to the archaeological marvel of Pompeii. The experience is elevated by your stay on an organic lemon farm, where a local family hosts you and introduces you to the secrets of limoncello making and the joys of Italian agriturismo.
With all accommodations, transport, and meals taken care of, you’re free to soak up the region’s stunning landscapes and savor its renowned cuisine. The unique selling point of this tour package lies in its deep cultural immersion—offering you the chance to live, eat, and explore like a true local. If you’re searching for a trip that blends trekking, culinary delights, and authentic hospitality, this Sorrento adventure is the perfect way to live your Italian dream.
7 days
Experience the full spectrum of Italian wonders on the 'Wonders of Italy' tour, an 11-day guided city sightseeing adventure starting and ending in Rome. Journey through Lucca, Florence, and Venice, cruise along Cinque Terre’s coastline, and savor a glass of Tuscan Chianti. Perfect for travelers who seek rich experiences at an easy pace, this tour package covers hotels, meals, and all transport. The unique selling point is the hands-on discovery of local crafts, including Venetian glassblowing, which adds depth to the exploration. For anyone longing for an immersive Italian journey, this trip brings the country’s artistry and flavors to life.
11 days
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
Dreaming of Italy’s classic wonders? The “Rome, Florence & Venice – 8 Days” sightseeing tour is perfectly tailored for experienced travelers and seniors seeking a comfortable yet enriching exploration of central Italy. Over eight days, travel by coach through Rome, Florence, and Venice, uncovering Renaissance architecture, medieval towns, and vibrant city life.
Enjoy guided walks through Rome, skip the line to marvel at St Peter’s Basilica and the Sistine Chapel, and lose yourself in Florence’s artistic treasures. Visit Siena’s medieval streets, savor Montepulciano’s Tuscan charm, and take in Bologna’s lively ambiance. In Venice, wander romantic canals and discover hidden gems with an expert guide.
This trip’s unique selling point is its comprehensive itinerary: it covers all the must-see sights and hidden corners, with expert commentary, included accommodations, and seamless transport—making it the ideal tour package for those who want to experience Italy’s highlights in comfort and style.
8 days
Discover some of Italy’s essentials during this six-day cultural trip. Visit the Eternal City of Rome, the National and the Vatican Museums. Explore Florence’s unique artistic and cultural centre. Discover the small medieval town of San Gimignano and stop by a typical Tuscan winery where you will visit the cellars and vineyards. Marvel at Siena’s gorgeous architecture and beautiful Main Square.
6 days
Rome, Florence, Venice—names that conjure centuries of art, culture, and history. The Jewels of Italy tour is a 7-day guided adventure that encapsulates the essence of Italy’s most enchanting cities, designed with both seniors and experienced travelers in mind. Explore the Leaning Tower of Pisa, marvel at Florence’s Duomo, and glide through Venice’s Grand Canal. With comfortable accommodation, included meals, and expert guides, this easy-paced trip ensures you enjoy every landmark without the rush. The USP: a thoughtfully curated tour package that delivers Italy’s timeless magic in just one unforgettable week, perfect for families and culture lovers alike.
7 days
Italy’s treasures await on the "Italian Discovery"—an 11-day journey that sweeps you through Rome, Florence, Sorrento, and beyond. Perfect for families, seniors, and young adults alike, this group tour showcases Renaissance splendors, Roman ruins, and the sun-drenched Amalfi Coast. Guided walks (2–3 miles a day) reveal the essence of each destination, from Florence’s art-filled streets to Sorrento’s seaside charm. Practical details—like euro tips and luggage limits—are handled, and the itinerary blends Northern and Southern Italy for a comprehensive experience. The unique selling point is its family-friendly structure, offering flexibility, expert guidance, and the chance to see Italy’s icons in comfort and style.
11 days
Unlock Italy’s most iconic sights and hidden secrets on the 7-day 'Italian Holiday' tour. Starting and ending in Rome, this city sightseeing adventure includes fast-track Vatican access, dining among Tuscan vineyards, and glassblowing demonstrations in Venice. Designed for travelers who appreciate both efficiency and depth, the tour package features comfortable hotels, meals, and seamless transport. What makes this trip stand out is the opportunity to enjoy Italy’s must-sees while indulging in authentic regional experiences. For those eager to savor Italy in a short, vibrant getaway, this tour delivers the perfect blend.
7 days
See all Italy Winter travel deals
Italy Winter Tour Types
Discover Italy Winter tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
10 Best Winter Tours in Italy
Join one of these handpicked Italy Winter tour packages, tailored to the season.
Italy’s treasures await on the "Italian Discovery"—an 11-day journey that sweeps you through Rome, Florence, Sorrento, and beyond. Perfect for families, seniors, and young adults alike, this group tour showcases Renaissance splendors, Roman ruins, and the sun-drenched Amalfi Coast. Guided walks (2–3 miles a day) reveal the essence of each destination, from Florence’s art-filled streets to Sorrento’s seaside charm. Practical details—like euro tips and luggage limits—are handled, and the itinerary blends Northern and Southern Italy for a comprehensive experience. The unique selling point is its family-friendly structure, offering flexibility, expert guidance, and the chance to see Italy’s icons in comfort and style.
Winter Departures
11 Jan, 25 Jan
Tour Type
Group Tour
11 days
Italy’s timeless beauty unfolds on the 'Easy Pace Italy' cultural journey, designed for mature travelers and families seeking unhurried exploration. This 10-day tour from Rome to Venice visits Renaissance Florence, Pisa’s Leaning Tower, and the tranquil Tuscan hills. Highlights include a guided visit to the Vatican Museums, lunch at an organic Tuscan farm, and a private boat ride through Venice’s scenic canals to St. Mark’s Square. Blending iconic landmarks with authentic culinary experiences, this tour package’s unique appeal lies in its relaxed itinerary and insider access to Italy’s art, history, and cuisine.
Winter Departures
11 Jan
Tour Type
Group Tour
10 days
The Amalfi Coast’s dramatic cliffs and pastel villages are yours to discover on the “Walking the Amalfi Coast” tour, an eight-day trekking adventure starting and ending in Bomerano. Designed for experienced travelers, this moderate-level trip features expertly guided walks through storied towns like Positano, Ravello, and Amalfi itself.
Follow ancient paths across hillsides, explore the haunting remains of Pompeii, and ascend Mount Vesuvius for sweeping views over the Bay of Naples. The highlight is the legendary Path of the Gods, hailed as one of the world’s greatest coastal walks. Enjoy the warm hospitality of a family-run hotel in the quiet village of Bomerano, away from crowded tourist spots.
All accommodations, meals, and transport are included, ensuring a relaxed and immersive experience. The main activity is trekking, supported by decades of local expertise. A special feature of the tour is the combination of iconic walks and authentic Italian hospitality, making it a standout for lovers of both nature and culture.
For a trip that blends Italy’s best scenery, history, and cuisine, this Amalfi Coast adventure is hard to beat.
Winter Departures
20 Dec, 27 Jun
Tour Type
Group Tour
8 days
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.
Winter Departures
12 Jan, 26 Jan
Tour Type
Group Tour
5 days
Rome, Venice, and Florence headline the 'Classical Italy' trip—a 5-day sightseeing tour ideally suited for seniors seeking a taste of Italy’s best cities. With all logistics, hotels, and meals included, this group trip allows you to relax and enjoy the highlights stress-free. The real draw is the concise itinerary—offering maximum cultural impact in a short, easy-paced journey designed to delight mature travelers.
Winter Departures
21 Dec, 28 Dec
Tour Type
Group Tour
5 days
Let the Amalfi Coast cast its spell on you during this 8-day food-focused tour, designed especially for seniors seeking both relaxation and cultural immersion. Departing from Naples and ending in Bomerano, this trip weaves through the glamorous island of Capri, the romantic streets of Ravello, and the legendary ruins of Pompeii and Herculaneum.
Based in the peaceful village of Agerola at a family-run hotel, you’ll enjoy a slower pace, savoring fresh Italian cuisine and admiring stunning coastal panoramas from iconic trails like the Path of the Gods. Explore chic Capri by boat, meander through fragrant lemon groves, and delve into the region’s storied past with guided visits to ancient archaeological wonders.
What distinguishes this tour package is its thoughtful blend of culinary delights, scenic walks, and cultural exploration—all tailored to provide comfort and meaningful connection. For those wishing to live la dolce vita while discovering one of Europe’s most dramatic shorelines, the Amalfi Coast awaits.
Winter Departures
27 Dec, 7 Mar
Tour Type
Group Tour
8 days
Rome, Florence, Venice—names that conjure centuries of art, culture, and history. The Jewels of Italy tour is a 7-day guided adventure that encapsulates the essence of Italy’s most enchanting cities, designed with both seniors and experienced travelers in mind. Explore the Leaning Tower of Pisa, marvel at Florence’s Duomo, and glide through Venice’s Grand Canal. With comfortable accommodation, included meals, and expert guides, this easy-paced trip ensures you enjoy every landmark without the rush. The USP: a thoughtfully curated tour package that delivers Italy’s timeless magic in just one unforgettable week, perfect for families and culture lovers alike.
Winter Departures
23 Dec
Tour Type
Group Tour
7 days
Travel from the shores of Venice to the ancient city of Rome on this 8-day guided tour of Italy. Begin your journey in Milan, where a festive feast complete with decadent Italian wines await you. In Venice, relax on a private boat as you pass by the iconic city to St Mark's Square, where you will see a gilded basilica anchoring the bustling piazza. Embark on a traditional gondola ride with your skilled Venetian gondolier, gliding along the canals while enjoying music. See the legendary Colosseum in Rome, then travel to the Vatican Museums, where a Local Expert will lead you through the papal art collection and to Michelangelo’s Sistine Chapel. Celebrate a fantastic trip over dinner in a local restaurant.
Winter Departures
19 Dec
Tour Type
Group Tour
8 days
Immerse yourself in Italy’s timeless magic with the "Italian Scene" tour, a 10-day countryside and village trip starting and ending in Rome. Discover Florence’s artistic pulse, Venice’s romantic canals, and the sun-drenched Italian Lakes, all at a gentle, easy pace perfect for families and seniors. Visit Sorrento’s citrus groves, capture memories at Pisa’s famed Leaning Tower, and honor Assisi’s spiritual calm. With expert guides, seamless transport, and comfortable hotels, this group tour makes each moment count. Its unique draw? The harmonious blend of Italy’s greatest cities and its picturesque rural heartlands, all wrapped into one unforgettable tour package.
Winter Departures
21 Dec
Tour Type
Group Tour
10 days
Dive headfirst into Europe’s greatest hits with the European Escapade—a 24-day whirlwind tour that starts and ends in London. From Amsterdam’s canals to the romance of Paris, the energy of Berlin, and the sun-soaked streets of Barcelona, this trip packs in legendary cities, Swiss Alps adventures, and exclusive Special Stays at Hopfgarten and Contiki’s Château de Cruix.
Tailored for young adults, this group tour delivers big on iconic sights, lively social scenes, and memorable moments. Upgrade to the ‘Plus’ for twin-share hotel comfort instead of the classic multi-share.
USP: An expertly curated city sightseeing tour package designed for those who want maximum Europe in minimum time—plus the perks of exclusive accommodations and unforgettable group experiences.
Winter Departures
22 Dec
Tour Type
Group Tour
24 days
Top Italy Tour Activities for Winter
From art and architecture tours to city sightseeing and others, here are some popular tour activities in Italy with departures in Winter.
Italy Winter Tours for all Age Groups
Italy tours in Winter designed for all ages—families, young adventurers, seniors, and everyone in between.
Reviews of our Italy Tours for Winter
Feedback from guests who toured Italy during Winter.
Lori A. | Traveled in December
Communication, accommodations, itinerary, and knowledge-it was all spot on! From the moment we requested information about the trip Collette had it covered. Our tour guide emailed before our trip providiing a touch of friendship and detailed information, Collette’s written packet kept us in the know while our tour guide’s daily written and verbal updates gave us peace of mind knowing step by step details. Our tour guide listened to the group and added either more guided site seeing or more free time as desired. It was truly a magical experience
Ann M. | Traveled in December
The BEST thing about the entire tour was the tour guide and the organization. Thanks to Collette, we were never left wondering what we were doing next!! I felt safe and cared for. My favorite memorable experience was seeing newly cannonized St. Carlo, in Assissi.
Edgardo B. | Traveled in December
I just love everything about the History of Rome. I love Vatican Square, the artifacts, history of the apostles and most of all to Carry the cross all the way inside the Vatican cathedral.
Dana C. | Traveled in December
The itinerary was great - loved spending 2 nights at most hotels! Felt like I got a great feel of several different regions of Itally. We had 6 family members traveling together and we all felt like it was a great trip. There were only 27 people in our tour group which was wonderful! Highly recommend this trip!
Jacqueline D. | Traveled in December
Awesome Tour Director Excellent itinerary. Outstanding coach driver . Great accommodation. Knowledgeable local Tour guides. Great attention to detail all round, ensuring it truly was the Dream vacation. Well done Trafalgar Team!
Bhavin S. | Traveled in December
it was a great 8 day tour that covered all the key tourist attractions that gives you a taste of what Europe has to offer. i'ts a great starting point for me next trip to Europe..
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