• Direct In Italy: +39 375 823 5314
  • Toll Free: 1-866-779-2565
A Christmas market illuminated in the town of Arezzo, Tuscany A historic square featuring the famous statue of Neptune in Florence

Private · Florence

A Tuscan & Umbrian Christmas Journey

12 Days Tuscany · Umbria

The Overview

Overview

Celebrate the holiday season in two of Italy's most enchanting regions—Tuscany and Umbria—on this 12-day festive journey. Immerse yourself in the timeless charm of Florence, the medieval allure of Siena, and the captivating holiday spirit of Perugia. This carefully curated tour combines rich history, world-renowned art, delicious cuisine, and festive Christmas markets, offering an unforgettable Italian holiday experience.

Your journey begins in Florence, where you'll explore Renaissance treasures, including the Duomo, Piazza della Signoria, and the Uffizi Gallery, all beautifully adorned for the holiday season. Wander through festive markets filled with handmade crafts, mulled wine, and traditional holiday treats. Enjoy leisurely meals at local trattorias, savoring the best of Tuscan cuisine.

Next, you’ll travel to Siena, a medieval gem where you’ll discover the UNESCO-listed historic center, including the famous Piazza del Campo and the Siena Cathedral, decorated for Christmas. Stroll through the Christmas markets, indulge in regional sweets, and relax with a glass of Vin Santo as you soak in the festive atmosphere. A scenic day trip to San Gimignano, renowned for its medieval towers, adds an extra layer of charm to this section of the tour.

The final leg of your journey takes you to Perugia, the heart of Umbria. Explore its medieval streets, admire the stunning architecture, and visit the underground Christmas market at Rocca Paolina. A visit to the Perugina Chocolate Factory will give you a taste of Italy’s famous Baci chocolates. Take a day trip to Assisi, the birthplace of St. Francis, where you’ll visit the Basilica di San Francesco, beautifully decorated for the season.

From guided tours to wine tastings and chocolate experiences, this tour offers a perfect blend of cultural immersion, festive cheer, and Italian hospitality, making it the ideal way to spend the holiday season in one of the most picturesque regions of the world.

Duration

12 days

11 nights

Pricing

On request

Tailored to your dates and group.

Celebrate Christmas in Italy with this 12-day tour through Florence, Siena, and Perugia. Explore historic landmarks, festive markets, and enjoy local cuisine, wine, and chocolate tastings. Immerse yourself in the holiday spirit and charm of Tuscany and Umbria.

Regions
Tuscany · Umbria
Tour Style
Private
Departs From
Florence
Meeting Point
Airport
Included Meals
Daily breakfast · 1 dinner · 1 wine tasting
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.

Tuscany

Chapter 1 · Days 1–8

Welcome to Tuscany

Tuscany is among the most beautiful regions of Italy. The gentle curves and slopes of the land will enchant you. Tuscany is as famous for its wine and cuisine as it is for its landscapes. Wine production focuses on red wines like Chianti, San Giovese, Rosso di Montalcino, Rosso di Montepulciano, Bolgheri, and others. Food is prepared with seasonal…

Explore Tuscany
Day 1

Tuscany, Florence

Arrival in Florence

  • Dinner
Arrival in Florence — photo 1 Arrival in Florence — photo 2 Arrival in Florence — photo 3 Arrival in Florence — photo 4 Arrival in Florence — photo 5

Arrive in Florence and enjoy a private transfer to your centrally located luxury hotel. Spend a leisurely afternoon exploring the festive streets, including Via de' Tornabuoni, where you can shop for Christmas gifts and admire the sparkling lights. End your evening with a delicious Tuscan dinner overlooking the Arno River.

Where we meet Airport
Day 2

Tuscany, Florence

Florence City Tour & Christmas Market

  • Breakfast
Florence City Tour & Christmas Market — photo 1 Florence City Tour & Christmas Market — photo 2 Florence City Tour & Christmas Market — photo 3 Florence City Tour & Christmas Market — photo 4 Florence City Tour & Christmas Market — photo 5

In the morning, embark on a private walking tour of Florence’s iconic landmarks, including the Duomo, Piazza della Signoria, and Ponte Vecchio. Afterward, indulge in a hearty lunch at a traditional trattoria. Spend the afternoon at the charming Christmas market in Piazza Santa Croce, where you can enjoy handmade crafts, mulled wine, and festive decorations. In the evening, take a stroll through the beautifully illuminated streets and enjoy an aperitivo.

Day 3

Tuscany, Florence

Florence Museums & Festivities

  • Breakfast
Florence Museums & Festivities — photo 1 Florence Museums & Festivities — photo 2 Florence Museums & Festivities — photo 3 Florence Museums & Festivities — photo 4 Florence Museums & Festivities — photo 5

Visit the renowned Uffizi Gallery with a private guide, admiring masterpieces from the Renaissance era. After lunch at a famous local restaurant, explore another Christmas market in Piazza del Duomo and warm up with chestnut cake and mulled wine. Conclude your evening with a peaceful walk to view the Christmas nativity scenes in historic churches like the Basilica di San Lorenzo.

Day 4

Tuscany, Fiesole

Day Trip to Fiesole

  • Breakfast
Day Trip to Fiesole — photo 1 Day Trip to Fiesole — photo 2 Day Trip to Fiesole — photo 3

Take a private excursion to the hilltop town of Fiesole, offering stunning views of Florence and a peaceful holiday ambiance. After a leisurely lunch at a local restaurant with panoramic views, return to Florence for a quiet evening, possibly visiting the Boboli Gardens.

Day 5

Tuscany, Siena

Transfer to Siena

  • Breakfast
Transfer to Siena — photo 1 Transfer to Siena — photo 2 Transfer to Siena — photo 3 Transfer to Siena — photo 4 Transfer to Siena — photo 5

After breakfast, enjoy a scenic transfer to Siena, where you'll stay in a charming hotel in the heart of the city. Spend the afternoon exploring Piazza del Campo, Siena’s medieval square, and the beautifully decorated Siena Cathedral. In the evening, dine at a local Osteria, offering Etruscan-inspired dishes.

Day 6

Tuscany, Siena

Siena Christmas Market & Walking Tour

  • Breakfast
Siena Christmas Market & Walking Tour — photo 1 Siena Christmas Market & Walking Tour — photo 2 Siena Christmas Market & Walking Tour — photo 3 Siena Christmas Market & Walking Tour — photo 4 Siena Christmas Market & Walking Tour — photo 5

Start your day at the Siena Christmas market in Piazza del Campo, where you can explore festive stalls selling traditional Tuscan treats and artisanal crafts. After lunch, take a private walking tour through Siena’s medieval streets, visiting highlights such as the Palazzo Pubblico and Torre del Mangia. End the day with a relaxing glass of Vin Santo and cantucci at a cozy wine bar.

Day 7

Tuscany, San Gimignano

Day Trip to San Gimignano

  • Breakfast
  • Wine Tasting
Day Trip to San Gimignano — photo 1 Day Trip to San Gimignano — photo 2 Day Trip to San Gimignano — photo 3 Day Trip to San Gimignano — photo 4 Day Trip to San Gimignano — photo 5

Take a private day trip to San Gimignano, a picturesque hilltop town known for its medieval towers. Wander through the town’s Christmas market, offering holiday crafts and local products. Enjoy a delicious lunch before visiting a nearby winery for a tasting of local wines. Return to Siena in the evening.

Day 8

Tuscany, Siena

Siena Museums & Relaxation

  • Breakfast
Siena Museums & Relaxation — photo 1 Siena Museums & Relaxation — photo 2 Siena Museums & Relaxation — photo 3 Siena Museums & Relaxation — photo 4 Siena Museums & Relaxation — photo 5

Visit the Santa Maria della Scala Museum Complex, a former medieval hospital turned museum, showcasing the rich art and history of Siena. After lunch, enjoy some free time to revisit the Christmas market or relax in Siena’s peaceful atmosphere. End the day with a farewell dinner at a local restaurant.

Umbria

Chapter 2 · Days 9–12

Welcome to Umbria

Umbria is one of the most beautiful regions in central Italy. South from Florence, north from Rome, it is often referred to as 'Italy's green heart', for it is the geographic center of the county.   it's lovely countryside and rolling sea of valleys and rolling hills are totally land-locked between the regions of Tuscany, Lazio and Marche .  Italy's capital…

Explore Umbria
Day 9

Umbria, Perugia

Transfer to Perugia

  • Breakfast
Transfer to Perugia — photo 1 Transfer to Perugia — photo 2 Transfer to Perugia — photo 3 Transfer to Perugia — photo 4 Transfer to Perugia — photo 5

After breakfast, transfer to Perugia, the capital of Umbria, and check in to a centrally located hotel. Spend the afternoon exploring the Christmas market at Rocca Paolina, an underground market set in a historical fortress. Enjoy a cozy dinner in this charming town.

Day 10

Umbria, Perugia

Perugia City Tour & Chocolate Experience

  • Breakfast
Perugia City Tour & Chocolate Experience — photo 1 Perugia City Tour & Chocolate Experience — photo 2 Perugia City Tour & Chocolate Experience — photo 3 Perugia City Tour & Chocolate Experience — photo 4 Perugia City Tour & Chocolate Experience — photo 5

Discover the historical center of Perugia on a private guided tour, visiting landmarks like the Fontana Maggiore and Palazzo dei Priori. After lunch, visit the Perugina Chocolate Factory for a special chocolate tasting and a tour of the famous Baci Perugina chocolate-making process. In the evening, stroll through Perugia’s beautifully lit streets and enjoy the festive atmosphere.

Day 11

Umbria, Assisi

Day Trip to Assisi

  • Breakfast
Day Trip to Assisi — photo 1 Day Trip to Assisi — photo 2

Take a private excursion to Assisi, a UNESCO World Heritage site and the birthplace of St. Francis. Visit the Basilica di San Francesco, decorated for Christmas, and explore the town’s Christmas market and nativity scenes. Return to Perugia in the evening.

Day 12

Umbria, Perugia

Departure from Perugia, Florence, or Rome

  • Breakfast
Departure from Perugia, Florence, or Rome — photo 1 Departure from Perugia, Florence, or Rome — photo 2 Departure from Perugia, Florence, or Rome — photo 3 Departure from Perugia, Florence, or Rome — photo 4 Departure from Perugia, Florence, or Rome — photo 5

On your final day, enjoy a leisurely breakfast before doing some last-minute shopping. Take a private transfer to the airport for your departure, either from Perugia, Florence, or Rome.

The journey ends

Farewell, Umbria

The details

Inclusions & Exclusions

What's Included

  • Accommodation
  • Private transfers
  • Guided tours
  • Museum visits
  • Breakfasts
  • Wine tasting
  • Chocolate experience
  • Christmas market visits

What's Not Included

  • Flights
  • Personal expenses
  • Optional activities
  • Tips
  • Travel insurance:Any meals not explicitly mentioned
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.

Where you are

Location

Italy Florence

Florence and beyond

12 days through Italy, with every stop chosen by the people who live here.

Where we meet

Airport

Where it starts

Florence

Nearby Experiences

Honor Your Beauty in Italy: A Wellness Experience with full access to the most beautiful spas of central Italy: December 1-10, 2025
Honor Your Beauty in Italy: A Wellness Experience with full access to the most beautiful spas of central Italy: December 1-10, 2025
The Leaning Tower of Pisa & Florence from Livorno with Wine Tastings in Montecarlo
The Leaning Tower of Pisa & Florence from Livorno with Wine Tastings in Montecarlo
Private Full day tour of Florence, its Hills and its great Museums
Private Full day tour of Florence, its Hills and its great Museums
Absolute Italy Escorted Tour, October 25th - November 5, 2025
Absolute Italy Escorted Tour, October 25th - November 5, 2025
Italy for Lovers: Private Tour of Italy including the Amalfi Coast, Capri, Rome, Florence, Tuscany & Venice
Italy for Lovers: Private Tour of Italy including the Amalfi Coast, Capri, Rome, Florence, Tuscany & Venice
Experience Florence: Accademmia, Duomo and the Loggia dei Lanzi
Experience Florence: Accademmia, Duomo and the Loggia dei Lanzi
Highlights of Tuscany: Gourmet Food and Wine Package
Highlights of Tuscany: Gourmet Food and Wine Package
11 days in Italy: from Venice to the Amalfi Coast
Italy's Northern Wine Country: Fine Wines, Food and Incredible Landscapes in Piedmont, Cinque Terre and Tuscany (Personalized Experiences)
Italy's Northern Wine Country: Fine Wines, Food and Incredible Landscapes in Piedmont, Cinque Terre and Tuscany (Personalized Experiences)
In the Footsteps of St. Francis
In the Footsteps of St. Francis
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.

Handpicked

Our Featured Properties

From the journal

Our Recent Blog

Peaks, Palaces & Prosecco® Venice Is Only the Beginning… Latest

Peaks, Palaces & Prosecco® Venice Is Only the Beginning…

Read article
Visit the journal
Keep exploring

Explore More of Italy

Curated Italy journeys and travel inspirations.

Weddings & Honeymoons Custom Group Tours Family Vacations Guaranteed Departure Small Group Tours Health & Wellness Retreats
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

12 days · Pricing on request

1-866-779-2565 Enquire Now
Direct In Italy: +39 375 823 5314 Toll Free: 1-866-779-2565
Home
About Italy Our Story Meet Our Team Press & Media Coverage
Travel Agents Affiliates Contact Us Book Consultation Trip Planning Customizable Tour