Italian Winter Wonderland: A Christmas Journey Through Northern Italy

Private · Milan

Italian Winter Wonderland: A Christmas Journey Through Northern Italy

12 Days Lombardia · Trentino-Alto-Adgie / South Tyrol · Veneto

The Overview

Overview

Experience the magic of Italy this holiday season with a luxurious 12-day private tour through its most iconic cities. From the fashion hub of Milan to the romantic canals of Venice, you'll explore festive Christmas markets, enjoy guided tours of historic landmarks, and indulge in regional delicacies. This exclusive journey takes you through the scenic beauty of Lake Como, the Alpine charm of Bolzano, and the romance of Verona, all while staying in luxury accommodations and enjoying personalized experiences. Celebrate the season in style with Italy’s rich culture, history, and holiday cheer.

Duration

12 days

11 nights

Pricing

On request

Tailored to your dates and group.

Experience the magic of Italy this holiday season with a luxurious 12-day private tour through its most iconic cities. From the fashion hub of Milan to the romantic canals of Venice, you'll explore festive Christmas markets, enjoy guided tours of historic landmarks...

Regions
Lombardia · Trentino-Alto-Adgie / South Tyrol · Veneto
Tour Style
Private
Departs From
Milan
Meeting Point
Milan Malpensa Airport
Included Meals
Daily breakfast · 1 lunch
Day by day

Itinerary

Follow the route as you read. The map traces each day of the journey, moving with you from place to place.

Lombardia

Chapter 1 · Days 1–3

Welcome to Lombardia

Lombardia is the northern most region of central Italy, lying between the Swiss Alps and the River Po. It is flanked on its east side by the Regions of Trentino and Veneto, and on its west by Piemonte.  To its south is the Region of Emilia Romagna.   Lakes, mountains and fertile plains surround Milan, Italy's one true metropolis: the country's financial…

Explore Lombardia
Day 1

Day 1: Arrival in Milan - Fashion, Culture & Christmas Lights


Your Italian holiday begins with a warm welcome in Milan. Upon arrival, a private transfer will whisk you away to your luxurious, centrally located hotel. After settling in, step out to explore the historic Galleria Vittorio Emanuele II, where world-class shopping awaits amidst the stunning 19th-century architecture. As evening falls, stroll through the vibrant Christmas market at Piazza Duomo. The square, glowing under festive lights, features stalls brimming with local crafts, food, and holiday gifts, setting the tone for your magical journey ahead.

Where we meet Milan Malpensa Airport
Day 2

Milan City Highlights & Sforza Castle Christmas Market

  • Breakfast


This morning, embark on a private guided tour of Milan, discovering its most iconic landmarks, including the majestic Duomo Cathedral, the famed La Scala opera house, and the historic Sforza Castle. After a leisurely lunch at a traditional Milanese restaurant, continue your festive exploration at the Oh Bej! Oh Bej! Christmas market near Sforza Castle, one of the city’s oldest and most beloved markets. Here, artisans display handmade goods, while the air is filled with the scent of roasted chestnuts and festive delights. Wrap up your day with an aperitivo in the charming Brera district, a perfect way to embrace Milan's local lifestyle.

Day 3

Day Trip to Lake Como - Festive Charm by the Water

  • Breakfast


Today, enjoy a scenic drive to the idyllic shores of Lake Como, where you'll explore Como’s enchanting Christmas market. Set against the backdrop of snow-capped mountains, the market offers wooden stalls filled with seasonal treats and local delicacies. Enjoy lunch at a lakeside restaurant with stunning views of the water before wandering through the historic Villa Olmo’s gardens. As evening approaches, return to Milan for a relaxing night in this stylish city.

Trentino-Alto-Adgie / South Tyrol

Chapter 2 · Days 4–6

Welcome to Trentino-Alto-Adgie / South Tyrol

Located in the very north of Italy, Trentino Alto Adige borders Austria and Switzerland.  It is best known for the glorious valleys and unique mountains. This setting encloses an extraordinary variety of landscapes: magnificent snow-capped mountaintops, woods, wide valleys, streams, lakes, the enchanting play of light between the spires of the Dolomites,…

Explore Trentino-Alto-Adgie / South Tyrol
Day 4

Journey to Bolzano - Alpine Beauty & Christmas Markets

  • Breakfast


Depart Milan this morning for the picturesque town of Bolzano, nestled in the heart of the Italian Alps. Your scenic private transfer will take you through breathtaking mountain landscapes. Upon arrival, check into your luxury hotel before venturing out to explore Bolzano’s famous Christmas market in Piazza Walther. Sample Tyrolean specialties such as speck and mulled wine as you wander among the twinkling stalls showcasing handcrafted ornaments and festive treats. Dine at a traditional South Tyrolean restaurant to savor the unique flavors of the region.

Day 5

Bolzano City Tour & Cooking Class

  • Breakfast
  • Lunch


Begin the day with a private guided walking tour of Bolzano’s charming historic center, where you'll visit the Museo Archeologico dell'Alto Adige, home to the famous Ötzi the Iceman. Afterward, participate in an intimate cooking class at a local home, where you'll learn to prepare traditional South Tyrolean dishes and enjoy the fruits of your labor for lunch. Spend the afternoon leisurely exploring Bolzano’s boutique shops and festive markets before relaxing at your hotel or enjoying the sparkling Christmas lights around the city.

Day 6

Day Trip to Merano - Spa Town and Christmas Markets

  • Breakfast


Today, you’ll take a short transfer to the spa town of Merano, known for its charming riverside Christmas market. Wander through festive stalls, savoring local specialties like apfelstrudel as the crisp mountain air surrounds you. Afterward, unwind in the famous Therme Merano, where you can soak in the warm, rejuvenating thermal baths – a perfect winter escape. Return to Bolzano in the evening, feeling refreshed and relaxed.

Veneto

Chapter 3 · Days 7–12

Welcome to Veneto

The Veneto region in Italy is one of the most remarkable and romatic regions. It offers visitors a journey through the land of Palladio, Giorgione and Titian, through enchanting mountains and vine carpeted valleys, to some of Italy's most romantic cities. A land of rolling hills, rivers, lakes and impressive architecture; Veneto is a stunning region in…

Explore Veneto
Day 7

Transfer to Verona - Romance and Christmas Magic

  • Breakfast


Depart Bolzano and head to Verona, the city of romance and Shakespeare’s famous Romeo and Juliet. Upon arrival, check into your luxurious hotel before exploring the Verona Christmas market in Piazza dei Signori, where wooden stalls offer German-style crafts, holiday treats, and local gifts. In the evening, enjoy a romantic dinner at one of Verona’s cozy restaurants, where you can savor regional dishes and soak in the holiday ambiance.

Day 8

Verona Historical Tour - Romance Meets History

  • Breakfast


Start your day with a private guided tour of Verona’s rich history, visiting iconic sites like Juliet’s House, where the famous balcony still stands, the ancient Arena di Verona, and the bustling Piazza delle Erbe. After a leisurely lunch at a local historic restaurant, spend the afternoon browsing Verona’s Christmas markets or artisanal shops known for leather goods and fine jewelry. As dusk falls, enjoy a magical evening walk through the illuminated streets, surrounded by Verona’s holiday charm.

Day 9

Day Trip to Lake Garda - Lakeside Christmas Markets

  • Breakfast


Today, head out for a serene day trip to Lake Garda, where you’ll visit the charming lakeside towns of Bardolino and Lazise. Both towns feature picturesque Christmas markets set along the water, offering stunning views and festive stalls filled with seasonal goodies. After enjoying a lakeside lunch, return to Verona for a quiet evening, perhaps indulging in a glass of wine at a local enoteca as you reflect on the day.

Day 10

Transfer to Venice - Canals and Christmas Lights

  • Breakfast


Travel from Verona to Venice, the city of canals, where holiday magic meets timeless beauty. After checking into your luxury hotel, explore Venice’s Christmas market in Campo Santo Stefano. Admire the exquisite craftsmanship of Murano glass, Venetian masks, and festive treats like pandoro and panettone. Enjoy dinner at a traditional Venetian restaurant, where seafood and local classics will delight your taste buds.

Day 11

Venice City Tour & Gondola Ride

  • Breakfast


Immerse yourself in Venice’s rich history with a private guided tour, visiting the awe-inspiring St. Mark’s Basilica, the grand Doge’s Palace, and the famous Rialto Bridge. After lunch in Piazza San Marco, continue to explore the city’s enchanting Christmas markets or indulge in a private gondola ride through the canals, where the serene winter atmosphere adds an extra layer of magic. In the evening, enjoy an aperitivo at a cozy wine bar, savoring Venice’s lively but intimate holiday spirit.

Day 12

Farewell to Venice - Final Stroll and Departure

  • Breakfast

On your final day, take the morning to wander through Venice’s winding streets at your leisure, or perhaps visit the colorful islands of Murano and Burano for some last-minute shopping. As your Italian holiday comes to an end, a private transfer will take you to Venice Marco Polo Airport for your departure, leaving you with unforgettable memories of Italy’s Christmas charm.

This 12-day luxury tour blends festive charm, cultural exploration, and relaxation, all while taking you through Italy’s most iconic cities and scenic regions.

The journey ends

Farewell, Veneto

The details

Inclusions & Exclusions

What's Included

  • Entrance fees to all sites and attractions included in the itinerary
  • Personalized wine or mulled wine tasting at a Christmas market (Bolzano)
  • Concierge service and 24/7 support throughout the trip
  • 11 nights at luxury, centrally-located hotels in Milan, Bolzano, Verona, and Venice
  • Private transfers between all destinations
  • Tours & Experiences
  • Meals mentioned in the itinerary

What's Not Included

  • Meals not specified in the itinerary (lunches and dinners are mostly on your own)
  • Optional activities and personal expenses
  • Gratuities for guides and drivers.
In their words

Traveler Reviews

Emily and David Davison Travelled with us

My husband and I just took a two week trip to Italy that was planned for us by Eleanor Kinchin-Smith. It was a fantastic trip and we could not have been more thrilled. We worked together with Ele to let her know about our interests and our style of travel. She planned the perfect trip with excellent private guides at all of our sites, professional drivers and lovely hotels. We arrived in Italy with all of our train and ferry reservations made by Ele, with tickets in hand. She was in touch with us daily throughout our trip to make sure that things were going smoothly. She was able to make a few changes to our itinerary as needed. We look forward to working with Ele again on our next trip and have put her in touch with another family member to help plan their trip as well.

Ron and Deb Crosby Travelled with us

Dear Guiseppe and Jesse,

We just returned from our most wonderful vacation to Italy and wanted to first thank you for putting together such a wonderful trip, and second to provide some feedback for the future.

Hotels

1. Hotel Sovestro in San Gimignano was wonderful. The staff were very friendly and helpful and made the first portion of our journey very stress free. They made us feel like we were part of their family. I would recommend it to anyone and would specifically ask for it if we were to make a return visit.

2. Hotel La Baia in Monterosso was nice and it's location was very good especially for us older folks humping luggage from/to the train station.

3. Hotel Lucchesi in Florence- what can I say expect FANTASTIC. The rooftop view at sunset is well worth it. Again very friendly and helpful staff. Would recommend it to everyone.

Wine Tour

Money well spent. We had a great time overall. The driver Mario was OUTSTANDING. He had lots of local knowledge as well as about winemaking. USE HIM AGAIN!!!

The various wineries we visited on tour:

Altesino- fantastic and they were not cheap on their pouring. Great experience.

Azienda Agricola Patrizia Cencion Sloaria- Again a great tour by one of the owner's daughters. We felt like we were the only thing on their mind although there were other customers there. A great way to complete the day.

Again we had a fantastic time and are very appreciative of everything you booked for us. We wish you continued success and if our travels should bring us back to Italy, we know who to call.

Leon and Michele Travelled with us

The trip was great we appreciate all the hard work you and your team invested to make our experience a once in a lifetime trip. We appreciate all the attention to the details in particular Giuseppe spending the time and the focus with us on the road and as we were exploring your great country.

Bob & Sandy Travelled with us

Jesse & Giuseppe,

Sandy and I have been looking through my slides of our trip to Southern Italy. We had such a good time with you and Giuseppe that we wanted to let you know again. You were the best guides ever.

Good to know

Frequently Asked Questions

Is this a private tour, or will we join a group?

Private. You travel with your own guide and driver, and the only people on the itinerary are the ones you bring with you. Nothing is shared with strangers, and the pace of each day is yours to set.

Can the itinerary be changed to suit us?

Yes. What you see here is a starting point, not a fixed departure. Tell us how long you have, what you love and what you would rather skip, and we will reshape it around you. A slower morning, an extra night somewhere you fell for, a different region entirely.

How do we start planning?

Send us a note using the form on this page, or call us on 1-866-779-2565. A travel specialist replies within one business day, usually with a few questions of their own. There is no cost and no obligation in asking.

When should we book?

The earlier the better, particularly for travel between May and September, when the best small hotels and the guides worth having are taken first. That said, we have put together beautiful trips at short notice, so ask and we will tell you honestly what is still possible for your dates.

Plan your journey

Start the Conversation

Quick Enquiry

Our travel specialists reply within one business day.

Keep exploring

Explore More of Italy

Curated Italy journeys and travel inspirations.

Cinque Terre, Italy

Ready to plan your journey?

Connect directly with a member of our team for expert guidance and fully customized travel across Italy and the Mediterranean.

Start Planning Your Trip
Direct In Italy: +39 375 823 5314 Toll Free: 1-866-779-2565
Home About Italy Travel Agents Contact Us Book Consultation Trip Planning Customizable Tour