Relaxed Winter Trip to Italy: Venice, Milan, Florence, & Rome

destination-icon12 Day Tour of Venice, Milan, Florence and Rome

Destinations on this trip: Venice,Milan,Florence,Rome

View of the Duomo and Florence's historic skyline in winter dusted by a coat of snow
Trevi Fountain in Rome covered in snow
St. Mark's Basilica and Square in Venice
Small boats line the embankment of a narrow canal in Venice

How Long Is the Relaxed Winter Trip to Italy Trip and What Does It Cost?

Visiting Museums & Art GalleriesLocal Cuisine & Wine
  • Duration
    12 days / 11 nights
  • Best time
    Jan-Dec
  • From
    $2999 / person (Flights not included)
Beat the tourist rush and experience Italy in its austere winter beauty. Explore Venice's iconic canals and secret squares, admire Milan’s gothic grandeur, and bask in Florence's Renaissance masterpieces. From the snow-dusted hills surrounding Lake Como to the bustling markets and cozy trattorias of Rome, winter in Italy offers unforgettable experiences without the crowds. Enjoy private guided tours, indulge in world-renowned Italian cuisine, and even learn to cook like a local in Rome with a hands-on class. Let our detailed travel guidance, available through our mobile app, lead you to Italy’s treasures in its quietest, most magical season.
  • Enjoy a private guided tour through Venice's San Marco Sestiere, including St. Mark’s Basilica.
  • Take in the stunning view from Milan's Duomo terraces and visit the Brera District for art & culture
  • See the masterpieces of the Uffizi Gallery and Michelangelo’s David during your stay in Florence.
  • Explore Ancient Rome with a private guide & take a self-guided walk through Rome’s historic squares.
  • Shop and cook like a local in Rome with a private cooking class.
Beat the tourist rush and experience Italy in its austere winter beauty. Explore Venice's iconic canals and secret squares, admire Milan’s gothic grandeur, and bask in Florence's Renaissance masterpieces. From the snow-dusted hills surrounding Lake Como to the bustling markets and cozy trattorias of Rome, winter in Italy offers unforgettable experiences without the crowds. Enjoy private guided tours, indulge in world-renowned Italian cuisine, and even learn to cook like a local in Rome with a hands-on class. Let our detailed travel guidance, available through our mobile app, lead you to Italy’s treasures in its quietest, most magical season.
  • Enjoy a private guided tour through Venice's San Marco Sestiere, including St. Mark’s Basilica.
  • Take in the stunning view from Milan's Duomo terraces and visit the Brera District for art & culture
  • See the masterpieces of the Uffizi Gallery and Michelangelo’s David during your stay in Florence.
  • Explore Ancient Rome with a private guide & take a self-guided walk through Rome’s historic squares.
  • Shop and cook like a local in Rome with a private cooking class.
Grand Canal  - Must-See Sight
Grand Canal
European History
Saint Mark's Basilica  - Must-See Sight
Saint Mark's Basilica
Architecture
Leonardo da Vinci's Last Supper - Must-See Sight
Leonardo da Vinci's Last Supper
Museums & Galleries
Duomo  - Must-See Sight
Duomo
Churches & Monasteries
Piazza del Duomo - Must-See Sight
Piazza del Duomo
Churches & Monasteries
Galleria dell'Accademia - Must-See Sight
Galleria dell'Accademia
Museums & Galleries
Oltrarno & Piazzale Michelangelo - Must-See Sight
Oltrarno & Piazzale Michelangelo
Cultural
Colosseum - Must-See Sight
Colosseum
Historic Landmarks
Vatican City - Must-See Sight
Vatican City
Churches & Monasteries

Must see sights

Grand Canal  - Must-See Sight
Grand Canal
European History
Saint Mark's Basilica  - Must-See Sight
Saint Mark's Basilica
Architecture
Leonardo da Vinci's Last Supper - Must-See Sight
Leonardo da Vinci's Last Supper
Museums & Galleries
Duomo  - Must-See Sight
Duomo
Churches & Monasteries
Piazza del Duomo - Must-See Sight
Piazza del Duomo
Churches & Monasteries
Galleria dell'Accademia - Must-See Sight
Galleria dell'Accademia
Museums & Galleries
Oltrarno & Piazzale Michelangelo - Must-See Sight
Oltrarno & Piazzale Michelangelo
Cultural
Colosseum - Must-See Sight
Colosseum
Historic Landmarks
Vatican City - Must-See Sight
Vatican City
Churches & Monasteries

Starting from

$2999

per person

no-flightNot included

Price varies by group size, hotel selection, and travel season.


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Where Does the Relaxed Winter Trip to Italy Trip Trip Go?

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VeniceMilanFlorenceRomeFlorence - Piazza del DuomoMilan - City CenterMilan - Sforzesco CastleMilan - Brera DistrictRome - Historic CenterVenice - St Mark's SquareRome - Vatican CityRome - Piazza Navona EveningVenice - DorsoduroVenice - San Marco Venice - San Polo and RialtoVenice - Zattere Dining OutFlorence - Palazzo Vecchio, Piazza Della SignoriaFlorence - Galleria dell'AccademiaRome - Castel Sant'AngeloRome - Spanish StepsRome - Villa Borghese GardensRome - Piazza VeneziaFlorence - Ponte Vecchio & Palazzo PittiFlorence - Uffizi GalleryRome - Ancient Rome Guided WalkMilan - Best of Milan Walking TourMilan - The Last SupperVenice - The Grand CanalFlorence - Dining Out In Santa CroceRome - Trastevere Evening
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Map data ©2026 GeoBasis-DE/BKG (©2009), Google, Inst. Geogr. Nacional
Map data ©2026 GeoBasis-DE/BKG (©2009), Google, Inst. Geogr. Nacional

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Relaxed Winter Trip to Italy Trip Timeline

Arrival

2 nights

Venice

Italy

Train: 2.5h

2 nights

Milan

Italy

Train: 2h

3 nights

Florence

Italy

Train: 2h

4 nights

Rome

Italy

Departure

What Does the Relaxed Winter Trip to Italy Trip Itinerary Look Like?

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Day 1

Arrive Venice

Day 1

Arrive Venice

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Mid-Day to Late Afternoon

St Mark's Square

St Mark's Square was the embodiment of The Most Serene Republic of Venice's power and prestige, and as such contains its most magnificent public buildings: the extraordinary golden mosaic-encrusted basilica of St Mark's, the exquisite Doge's Palace, the all-seeing bell tower, the Bibliotecca Marciana library, and what is nowadays the famous Correr Museum. If timed correctly, it is possible to see all these sights on your own within half a day, although a guide can make the process much more efficient (and more educational as well). Keep in mind that the square is one of the most heavily touristed places in the world, so crowds and lines can be an issue. St Mark the Evangelist was not the patrion saint of Venice until 829 AD, when two Venetian merchants stole St. Mark's remains from their original resting place in a chuch in Alexandria, Egypt, and then smuggled the relics home trussed up in a canvas sheet. The pretext for the theft was that the Muslim conquerors of Alexandria were expected to defile and plunder the church. While this may have been true, it is no coincidence that bringing such an important saint's relics to Venice was hugely important politically and signaled Venice's place as a rising independent power. A church was built to house the relics, and St. Mark's Square was established as the spiritual and political heart of the city.

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Day 1

Arrive Venice


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To Be Determined:

Transfer from Airport

Mid-Day to Late Afternoon:

St Mark's Square

Late Afternoon:

The Grand Canal

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Day 2

Venice

Day 2

Venice

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Morning/Mid-Day

The Dorsoduro District

Discover the less well-known sestiere (district) of Dorsoduro and visit its world-famous art collections at Gallerie dell'Academia, the Peggy Guggenheim Collection, and Cà Rezzonico. Once a haven for artists before rising rents drove them out, it is still a charming and unique district with many lively spots, such as the Campo Santa Margherita, one of Venice's largest squares. Be sure to take a walk along its enchanting waterfront promenade known as Zattere and explore the cafes along its canals.

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Day 2

Venice

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Day 3

Venice to Milan

Day 3

Venice to Milan

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Morning/Mid-Day

San Polo District

The graceful arch of the Rialto Bridge is perhaps the single most iconic sight in Venice since nearly everyone passes beneath it on their journey along the Grand Canal. It connects Venice's two most visited districts, San Marco and San Polo. While San Marco is famous for St. Mark's Square, San Polo more than holds its own as a must-see destination, as it contains some of the city's oldest neighborhoods and most picturesque canals and bridges. It is also home to some of the best restaurants in Venice, and admittedly some of its worst tourist traps as well. Among many highlights is the bustling Rialto Market, which was once one of medieval Europe's busiest financial and trade markets, and still does a brisk trade in fresh seafood and produce.

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Day 3

Venice to Milan

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Day 4

Milan

Day 4

Milan

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9:00 AM - 12:00 PM

Guided Walk in Milan

Milan is the center of business and the capital of Italian fashion, but it also has an ancient heritage and a fascinating history; here you find some of the greatest masterpieces of Italian art! Together with your guide, you’ll explore the magnificent Duomo, Galleria, Scala opera house, merchant square, financial district, food street, and Sforza Castle.

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Day 4

Milan

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Day 5

Milan to Florence

Day 5

Milan to Florence

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Morning/Mid-Day

The Last Supper

Preserved in the refectory (i.e. the dining hall) of the convent of Santa Maria delle Grazie, Leonardo da Vinci's The Last Supper is not only one of Milan's top attractions, but one of the most famous paintings in the world. Painted between 1494 and 1498, it depicts the last "dinner" between Jesus and his apostles. The painting shows the dramatic moment in which Christ reveals that he will be betrayed by one of the twelve apostles sitting at the table, as told in the Gospel of St John.  A mandatory reservation has to be made either online or over the phone if you wish to visit The Last Supper. Reservations for each calendar month go on sale approximately 3 months in advance. Spots are very limited, so if you miss your chance, then the best bet is a guided tour which includes The Last Supper. With so much to learn about the painting, seeing it with an expert is a good idea in any case. The Last Supper of Leonardo da Vinci is undoubtedly one of the most important works of art of all time, but Milan is a city full of surprises and you'll find numerous other sights linked to the great artist just a short distance away.

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Day 5

Milan to Florence

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Day 6

Florence

Day 6

Florence

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Morning/Mid-Day

Uffizi Gallery

As the capital of the Renaissance, it's only fitting that Florence should also host Italy's greatest art gallery at the Uffizi. It's understandably busy throughout the year, but it's nevertheless worth the crowds to see to see some of the most sumptuous masterpieces of Renaissance art, including Botticelli's Primavera and Venus, and works by Michelangelo and Da Vinci. If you're planning to visit other galleries and museums in Florence, then it's definitely worth investing in a Firenze Card, which gives you free entry and priority access to 72 venues in the city. At a minimum, you should book ahead for the Uffizi to avoid very long queues.

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Day 6

Florence

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Day 7

Florence

Day 7

Florence

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9:00 AM - 12:00 PM

Private Walking Tour

Enjoy a 3-hour private walking tour of Florence, the perfect introduction to the masterpieces of this city. Stroll around the historic center and take in sights such as the Palazzo Vecchio, Ponte Vecchio, Piazza Della Signora and end your tour at the famous Galleria dell'Accademia, where you can choose to enter to see Michelangelo's marble masterpiece, the statue of David. Please note that entry tickets to the gallery is not included and you must purchase them in advance.

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Day 7

Florence

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Day 8

Florence to Rome

Day 8

Florence to Rome

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9:15 AM

Transfer to Rail Station

Most trains depart from Firenza S.M.N. (i.e. Florence Santa Maria Novella Station) station, the largest station in the city. Before spending money on a transfer, be sure to check whether your hotel is within easy walking distance. Also consider that public transport is the cheapest and sometimes fastest option; trams and buses drop off next to the station. Uber is available in Florence, and if staying at a hotel, they can order a reliable taxi. Some private transfers will even help with your bags.

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Day 8

Florence to Rome

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Day 9

Rome

Day 9

Rome

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Morning

Rome's Historic Center

Rome's tangled historical center is packed full of some of the most fascinating and incredible sights. Explore elegant squares and piazzas, centuries-year-old churches, and baroque fountains and wander at leisure the labyrinth of ancient Roman cobbled lanes. Highlights include the Baroque grandeur of Piazza Navona and the great and endlessly copied Roman Pantheon.

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Day 9

Rome

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Day 10

Rome

Day 10

Rome

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Early Morning to Afternoon

Vatican City

Rome is unique in the world in that it contains an independent country within its city limits - the Vatican City, from where the Pope administers the Catholic Church. The symbolic center of Catholicism is St Peter's Basilica, the second-largest Catholic church in the world and among the most beautiful. The Vatican Museum contains one of the greatest collections of art in existence, including Michelangelo's jaw-dropping Sistine Chapel. The popes had a bigger influence on Rome than just the collection of art. The Pope's title is actually Bishop of Rome, and popes administed the city for centuries, shaping its architecture & public spaces. Rome was re-built to be an example of urban beauty, and the Vatican was meant to be the showcase within the showcase. Their success is evident from the throngs of visitors who flock here even today.

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Day 10

Rome

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Day 11

Rome

Day 11

Rome

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9:30 AM - 3:00 PM

Cooking Class

Join this ultimate food experience in Rome, where you'll have the opportunity to prepare local dishes and or delicacies in a relaxed and welcoming home located in the heart of Ancient Rome. Get your hands stuck in and prepare a seasonal menu paired with local wine.

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Day 11

Rome

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Day 12

Depart Rome

Day 12

Depart Rome

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To Be Determined

Private Transfer to Rome Fiumicino or Ciampino Airport

A car service will pick you up from your hotel and take you directly to Rome Fiumicino Airport. This is a private transfer for you and your travel party. You do not need to pay the driver as the cost of the private transfer is included in your itinerary.   IMPORTANT NOTE:  Please be aware the car service can fit up to 1 checked item of luggage and 1 personal item per person, such as a purse or small backpack. If you think you will have more baggage, please inform your travel consultant as this may result in an additional fee.

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Day 12

Depart Rome

What's Included in the Relaxed Winter Trip to Italy Trip Trip?

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Pre-Paid Tours and Activities:

  • 'First Walk' Guided Tour in Venice
  • Best of Milan Private Walking Tour
  • Florence in Half a Day: Guided Highlights Walk
  • Heart of the Empire - Private Tour of Ancient Rome & the Colosseum
  • Private Cooking Class in Rome
  • City Card for Rome, including discounts to many popular attractions
train

Pre-Paid Transportation:

  • 2nd Class Train Tickets from Venice-Milan
  • 2nd Class Train Tickets from Milan-Florence
  • 2nd Class Train Tickets from Florence-Rome
  • Public Transport Tickets for Venice and Rome
  • Private Transfer from Rome Termini Rail Station
  • Private Transfer to Rome Fiumicino or Ciampino Airport
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Accommodation:

  • 2 nights at a hotel of your choice in Venice
  • 2 nights at a hotel of your choice in Milan
  • 3 nights at a hotel of your choice in Florence
  • 4 nights at a hotel of your choice in Rome
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