10 Best Italy Multiday Tours in Winter

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Discovering Milan - Winter tours

(1 review )

Trip customizable

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Join this four-day short break in Milan and discover Sforza Castle the most impressive urban castle in Europe, and Duomo Cathedral, a striking example of Gothic art and the largest church in Italy. Admire the famous Last Supper of Leonardo Da Vinci, enjoy the Navigli district and take a trip to Lake Como and Lugano. Don’t miss the shopping opportunity as Milan is one of the most important cities in the world of fashion.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english

Destinations

Milan

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Duration4 days

From

USD 820

USD 697

Saving

USD 123

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Discovery of Italy: 8 Days - Winter tours

4.5

(2 reviews )

Trip customizable

Best price guaranteed

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.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, The Vati

Rome, Florence, Venice, The Vatican, Assisi, Montepulciano, Siena, Tuscany, Bologna, Padua

Duration8 days

From

USD 2,750

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Venetian Treasures (port-to-port cruise) - Winter tours

(1 review )

No booking fees

Best price guaranteed

This cruise was great. The only complaint is I did receive information on how to book optional excursions in advance.

CruiseCity sightseeing

Tour Type

Cruise Tour

Accommodation

Ship Cabin

Age Range

18-79 yrs

Operated in

english

Destinations

Venice, Chioggia

Duration5 days

From

USD 647

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Italian Intermezzo - Winter tours

4.7

(65 reviews )

No booking fees

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This tour is the BEST way to see all the infamous spots in Italy, plus local hidden gems, at a reasonable cost and if you are short on time (we had a school break time limitation). It covered everything! We budgeted for the add-ons, especially those with meals, but you could choose to have more free time if you wanted. The food was extraordinary, the bus was roomy and immaculately clean, our driver Antonello was superb, and our Travel Director Anneleis was amazing! She was so talented at integrating the tour highlights, guests, keeping it fun even in the rainy weather, knowledgeable, and able to troubleshoot anything to ensure we had the best experience of a lifetime!! I would love to go back and explore Southern Italy next. The hotels were elegant (only one was just "OK" only because it was in need of some renovations) and the service with our luggage, tipping, etc. was seamless. I highly recommend the Italian Intermezzo tour and Insight Vacations. Favoloso!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Rome, Venice, Florence

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Duration8 days

From

USD 3,225

USD 2,973

Saving

USD 252

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Amazing Italy - Winter tours

(3 reviews )

Trip customizable

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Absolutely incredible! Italy’s history, food, and charm blew us away. The small group setting was perfect, and everything was tailored for Canadian travelers. Highly recommend!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Rome, Florence, Verona, Sorrento

Rome, Florence, Verona, Sorrento, Venice, Perugia, Naples, Salerno, Siena, Genoa, Milan

Duration15 days

From

USD 2,729

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Private Gourmet Wine Tour in Tuscany - Winter tours

4.5

(2 reviews )

Trip customizable

Best price guaranteed

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

Food toursWine tasting tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

22-89 yrs

Operated in

english, german

Destinations

Tuscany, Chianti, Florence, Sien

Tuscany, Chianti, Florence, Siena, Pisa

Duration4 days

From

USD 2,846

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A Taste of Italy: 11 Days - Classic - Winter tours

Trip customizable

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Traveling from eternal Rome and up through the hazy hills of Tuscany, you’ll spend eleven days sampling the best of Assisi, Siena, Florence, Bologna, Venice, the Tuscan wine region, and Capri! Catch the spirit of la vita bella as you explore elegant Florentine piazzas, rummage through handcrafted artisanal treasures, sip world-class wines, and float down intimate Venetian canals. You will then discover the treasures along Italy’s Amalfi Coast, to sun-bleached Capri before returning to Rome!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Lazio, Sorrento

Duration11 days

From

USD 2,348

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Easy Pace Italy - Winter tours

4.8

(114 reviews )

No booking fees

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Good introductory cross-section in major cities. Good balance of scheduled vs. free time. Would like a little more emphasis on art--especially Uffizi Gallery and Pisan Camposanto--plus entry into St. Mark's/Doge's Palace and Duomo church (rather than some of the shopping stuff). A little too much commercial, too little history/art. (Some of guides under-informed, including one who said Galileo discovered the "two planets" around Jupiter!).

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Florence

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Duration10 days

From

USD 5,175

USD 4,835

Saving

USD 340

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Simply Italy - Winter tours

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Welcome to 15 days of pure Italian travel immersion. Covering Rome, Florence, Venice and beyond, this one brings you the blissful best of this soul-stirring country. Explore Rome's historical highlights, travel through the streets of Michelangelo's Florence, indulge in some authentic pasta on the Amalfi Coast. Stop by to see the stooping slopes of Sorrento in the breezy winter. And that's just an aperitivo. Beauty, romance and all the pasta you can fit in; the good life just got even better. That's amore!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Naples, Amalfi Coast, Flor

Rome, Naples, Amalfi Coast, Florence, Cinque Terre, Milan, Venice

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Duration15 days

From

USD 2,755

USD 2,538

Saving

USD 217

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Italian Espresso - Winter tours

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10 days of la dolce vita, pronto. This one is pure Italian travel, covering all the big bucket-list destinations of Venice, Florence & Rome, plus the smaller charms of Pisa, Verona, and Siena. We'll ooh and aah over antipasto & chianti, dine on regional specialities in local trattorias, boat through the canals and islands of Venice, and explore the architecturally magnificent city of Florence. Expect plenty of world-famous espresso & pizza on the way.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Venice, Florence, Cinque T

Rome, Venice, Florence, Cinque Terre, Milan

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Duration10 days

From

USD 2,035

USD 1,875

Saving

USD 160

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Rome, Florence & Venice - 8 days - Winter tours

(1 review )

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COACH TOUR: Take in the best of central Italy on this 8-day group tour which starts and ends in Rome. Explore the capital, visit medieval Siena, and relax in the Tuscan town of Montepulciano. Marvel at the stunning Renaissance architecture of Florence, enjoy a stroll around Bologna and visit Padua. Discover the highlights of Venice on a walking tour and skip the line at the Vatican City to see St Peter's Basilica and the impressive Sistine Chapel.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Florence, Venice

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Duration8 days

From

USD 2,235

USD 1,900

Saving

USD 335

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Italian Escape - Winter tours

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This all-Italian adventure kicks off in the historic heart of Rome, then heads to Naples—the birthplace of pizza. You'll explore the perfectly preserved ruins of Pompeii before soaking up the sun and sipping limoncello along the stunning Amalfi Coast (with a stop in postcard-perfect Sorrento, of course). By the end of this unforgettable 6-day Italian escape, you'll have a belly full of pizza, a camera full of memories, and a serious craving to come back for more.

Food tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Pisa

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Duration6 days

From

USD 1,331

USD 1,227

Saving

USD 104

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Discover Italy - Winter tours

4.5

(21 reviews )

No booking fees

Best price guaranteed

Every thing was just perfect

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Florence, Genoa, M

Rome, Venice, Florence, Genoa, Milan, Verona

Duration9 days

From

USD 1,258

USD 1,220

Saving

USD 38

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Europe Highlights - Winter tours

4.8

(118 reviews )

No booking fees

Best price guaranteed

This was our first time to Europe and it did not disappoint! Right from day 1 the fun started! Jared was our tour leader, if you ever get the chance to tour with him, you are lucky. He was fantastic!!! His knowledge of the places we stopped was expansive and he made it interesting to learn the history! Florentin our driver was a rock for us! He got us safely to our destinations and always had a smile on his face! We forged friendships on this tour that made this the most memorable trip! We laughed a lot !!! I am so glad my daughter and I were lucky enough to have such an amazing tour leader, driver and fellow travellers that only made all the amazing places we saw, better! Thank you

MountainsCity sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

10-99 yrs

Operated in

english

Destinations

Rome, Venice, Amsterdam, Tuscany

Rome, Venice, Amsterdam, Tuscany, Munich, Pisa, Swiss Alps, Rhine, Paris, Lauterbrunnen, Montecatini Terme

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Duration10 days

From

USD 2,275

USD 2,025

Saving

USD 250

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Combine Italy in Winter with Nearby Countries for an Unforgettable Trip

See tours with itineraries going through multiple countries, including Italy

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Alternatively, explore tours that are exclusively just Italy and Spain, Germany and Italy or France and Italy.

All Italy Tours in Winter

Page 3 of 191 Trips in Italy with 2,919 Reviews

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Discovering Milan - Winter tours

Discovery of Italy: 8 Days - Winter tours

Venetian Treasures (port-to-port cruise) - Winter tours

Italian Intermezzo - Winter tours

Amazing Italy - Winter tours

Private Gourmet Wine Tour in Tuscany - Winter tours

A Taste of Italy: 11 Days - Classic - Winter tours

Easy Pace Italy - Winter tours

Simply Italy - Winter tours

Italian Espresso - Winter tours

Rome, Florence & Venice - 8 days - Winter tours

Italian Escape - Winter tours

Discover Italy - Winter tours

Europe Highlights - Winter tours

Page 3 of 191 Trips in Italy with 2,919 Reviews

Combine Italy in Winter with Nearby Countries for an Unforgettable Trip

Europe

Asia

South America

Africa

North America

Oceania

Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

All Italy Tours in Winter

Page 3 of 191 Trips in Italy with 2,919 Reviews

See Italy tours by duration

Page 3 of 191 Trips in Italy with 2,919 Reviews