Don't miss out on Italy's best experiences! Book early from over 200 tours departing in January 2001. Secure better prices, guaranteed spots, and peace of mind with more than 3,900 verified traveler experiences.
Get a customized trip to Italy in Winter
Plan a multi-country or regional adventure across Italy in Winter, with help from a local expert.
This tour will take you on a memorable train ride across the major touristic cities of Italy. You’ll begin by exploring Rome, with stunning feats of civilization, modern and age-old alike. Colosseum, Navona Square, Pantheon, Spain Square, and Trevi Fountain are a few places that you can visit. The next place where you’ll take a train would be Florence. History, art, countryside, and delicious food are the gist of what this capital city of Tuscany has in store for you. Accademia and Uffizi Galleries are a must-visit. After Florence, The City of Water, Venice, awaits your arrival. Though the journey to Venice via rail is gorgeous, the city itself has its charm. Riding into a gondola through the Grand Canal and being mesmerized by the city’s beauty should be on your list. In addition, take a walking tour covering St Mark’s Square, Doge's Palace, Bell Tower, etc. Finally, we are at the last city of this train tour—Milan. An epitome of great fashion and design, Milan is a heart stealer. Apart from the latest cultural trends, you can even get a slice of history by visiting the Milan Cathedral. Also, ensure not to miss Leonardo Da Vinci’s stupefying Cenacolo, the Last Supper, which is one of the most famous artworks in the world. This train journey is one of the most popular Italy travel packages, offering a comprehensive tour of Italy's iconic cities.
Explorer
Tour Type
Independent TourTypically a private tour undertaken by one or two travelers
Experience the heart of Tuscany with a gastronomic escape at a historic Tuscan villa. This deliciously curated package includes hands-on cooking and pizza-making classes with the warm and welcoming chef, plus a scenic wine tasting at a local farm near San Gimignano. Enjoy time to relax or explore the nearby medieval gems of Siena and Florence, all while staying in a villa once home to popes and princes. With unforgettable meals, charming towns, and authentic Tuscan hospitality, this is the perfect getaway for food and wine lovers seeking a true taste of Italy
Step into the heart of the Eternal City with the "Gastronomic & Ancient Rome – 5 days" private explorer tour, tailored for experienced travelers and seniors who appreciate history and cuisine in equal measure. Explore Rome’s iconic sites—the Colosseum, Roman Forum, and Vatican City—then venture to Tivoli for its UNESCO-listed villas.
Dive into Italy’s culinary traditions with a hands-on pizza-making class and a guided food walking tour, sampling classic Roman dishes along the way. Accommodations, transport, and some meals are included for a seamless experience.
The tour package’s USP is its immersive blend of ancient heritage and culinary delight—ensuring you savor both Rome’s rich history and its legendary flavors in just five days.
Uncover Florence’s artistic treasures and rolling vineyards on the "Florence Discovery & Wine Tasting – 4 days" private city sightseeing trip, ideal for experienced travelers and seniors. Enjoy a guided walking tour and fast-track entry to the Galleria dell’Accademia, then explore at your own pace with ample free time.
Venture into the Chianti region for a day of wine tasting and indulge in a lunch of regional specialties. With accommodation, transport, and select meals included, this tour package’s unique charm lies in its balanced blend of cultural exploration and culinary pleasure—perfect for those wanting to savor Florence’s best in comfort.
Fuel your passion for Italian cuisine and culture on the "Gastronomic Bologna, Ferrari & Parma – 4 days" private explorer tour. Designed for experienced travelers and seniors, this easy-paced trip is a culinary pilgrimage through Bologna and the famed Food Valley of Modena and Parma.
Enjoy a tasting at a historic vinegar factory, visit the house museum of Luciano Pavarotti, and delight in a countryside lunch featuring local produce and handmade Tortellini. Experience the legacy of Ferrari in Maranello and embark on a private walking tour of Parma’s historic highlights, sampling traditional dishes and local wine.
The unique selling point of this tour package is its deep dive into Emilia-Romagna’s culinary and automotive heritage—offering exclusive tastings, cultural insights, and the perfect balance of sightseeing and gastronomic indulgence.
Set sail from Naples for an enchanting 8-day voyage through southern Italy with the 'Naples, the Amalfi Coast, and Sicily' cruise tour. Each port unveils a new chapter: wander ancient Pompeii and Herculaneum, savor the flavors and sights of Naples’ Old Town, and cruise past the volcanic wonders of the UNESCO-listed Aeolian Islands.
Relax in the authentic charm of cliffside Tropea and soak up the breathtaking Amalfi Coast. With all-inclusive cabin accommodation and carefully curated excursions, this cruise’s USP is its unique blend of ancient ruins, natural wonders, and Mediterranean charm—making it an exceptional way to discover southern Italy’s riches.
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.
Experience Tuscany’s timeless allure on the "Florence, San Gimignano & Siena – 4 days" private explorer tour, crafted for experienced travelers and seniors who seek both cultural highlights and leisure. Enjoy skip-the-line access to Florence’s Galleria dell’Accademia, home to Michelangelo’s David, and spend three nights in the heart of the Renaissance capital.
Explore the medieval towers of San Gimignano and the vibrant Piazza del Campo in Siena, with an included wine tasting to showcase the region’s flavors. With accommodation, transport, and meals arranged, this private trip stands out for its in-depth, stress-free immersion into Tuscany’s art, history, and gastronomy.
Get ready for the magic of Christmas on this pre-holiday cruise in Italy and Sicily Naples has historical monuments and archaeological sites, while the Aeolian Islands are in a league of their own. This romantic cruise includes visits to the ancient theater in Taormina, with Mount Etna as the backdrop, Calabria "the toe of the boot" and the Amalfi Coast. And we can't forget the legendary Isle of Capri with its panoramic views of the Gulf of Naples. Italian Christmas traditions are in the spotlight on this cruise! Discover the famous Neapolitan nativity art and magnificent scenes exposed in small boutiques and workshops in the city's older neighborhoods. Each hand-crafted figure is one-of-a-kind. Christmas charm reigns in the shops all year round.
Imagine cruising scenic highways from Rome to the sun-soaked Amalfi Coast—this 6-day self-drive sightseeing tour invites experienced travelers to experience Italy’s beauty at their own rhythm. Begin in Rome, weaving through picturesque villages and ancient ruins en route to the dramatic cliffs and azure waters of Amalfi. Delight in the colorful architecture, explore iconic landmarks such as Positano and Ravello, and soak up the Mediterranean ambiance. The true highlight of this journey is the freedom to discover hidden gems and timeless classics alike, blending Italy’s rich culture with awe-inspiring landscapes and culinary delights.
City sightseeing
Tour Type
Independent TourTypically a private tour undertaken by one or two travelers
Simple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Comfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
Upscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.
Guide Types
Page 16 of 202 Trips in Italy with 3,958 Reviews
Most Popular
Most Popular
Lowest Price First
Highest Price First
Lowest Duration First
Highest Duration First
Highest Discount
Activities
Combine Italy in Winter with Nearby Countries for an Unforgettable Trip
See tours with itineraries going through multiple countries, including Italy
Alessandra GalassiTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
Danilo CataniaTravel Expert in Italy
