Chapter One
Venice becomes intimate.
Arrive across the lagoon, walk the lanes around San Marco and discover how winter quiet lets the city's details come forward: water, stone, bells and the glow of evening.
Now Journey holiday signature
Italy at Christmas Time
The Original 10-Day Small Group Holiday Journey.
Venice → Florence → San Gimignano → Cortona → Rome
- 4 to 12 guests
- Max 16
- Tour Captain hosted
- Deluxe & Classic hotel collections
- 50+ five-star reviews
No obligation. No pressure.
10 Days / 9 NightsBalanced holiday pace
Venice to RomeFour Italian chapters
4–12 GuestsMaximum 16
Two CollectionsDeluxe & Classic
Tour CaptainHosted throughout
Your Journey Ahead
Four festive chapters. One seamless story.
Your Journey at a Glance
Scroll from Venice's lagoon through Renaissance Florence and the Tuscan hills to Rome dressed for the season.
Scroll through the journeySwipe through the journey
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01VeniceArrive by water, discover San Marco in its winter light and settle into the quieter rhythm of the lagoon.
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02FlorenceRenaissance landmarks, local holiday traditions and time for markets, churches and evening streets.
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03Tuscany & CortonaSan Gimignano, a winery estate and a slower hill-town rhythm warm the heart of the journey.
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04RomeAncient Rome, glowing piazzas and festive traditions frame the final days and farewell dinner.
Journey Story
Italy, illuminated by the season.
The route follows Italy's great cultural arc while the holidays change its atmosphere: fewer crowds, glowing piazzas, regional traditions and evenings that feel unmistakably local.
Chapter Two
Florence holds the Renaissance close.
Giotto's Bell Tower, the Baptistery, the Duomo and the city's historic piazzas create a holiday chapter shaped by art, tradition and time to explore on your own terms.
Chapter Three
Then Tuscany softens the pace.
San Gimignano's towers, a winery tasting and Cortona's Etruscan streets shift the journey into a slower register of vineyard roads, hill towns and regional flavors.
Final Chapter
Rome becomes the celebration.
The Pantheon, Piazza Navona, Vatican City and ancient Rome unfold amid lights, nativity scenes and the city's irrepressible energy before a final dinner together.
Day by day
The Complete Itinerary
Open each day for the full journey. Included experiences and optional choices are labeled clearly.
Chapter One
Days 1–2
Venice
Arrival by water, a first Discovery Walk, holiday traditions and an included gondola experience begin the journey in true Venetian style.
The lagoon opens the story.
Venice is not rushed. The first two days create room to arrive, orient and experience the city after the day visitors drift away.
01Day OneWelcome to Venice
Included
Upon arrival at Venice Marco Polo Airport, enjoy the included Airport Arrival Transfer with Meet & Greet. Board a water taxi across the lagoon to San Marco island, check in and relax until the afternoon Discovery Walk.
Discovery Walk: Venice at Christmas Time. Your Tour Captain introduces Piazza San Marco, the Campanile, the Grand Canal and the hidden lanes that make Venice feel personal.
After time at leisure, meet for a special Welcome to Venice evening and an included dinner featuring regional cuisine, wines and premium beverages.
What's Included
- Airport meet-and-greet and arrival transfer
- Water taxi across the lagoon
- Tour Captain-led Venice Discovery Walk
- Welcome Dinner with wine and premium beverages
- Venice hotel accommodation
02Day TwoExploring Venice
Optional
Venice's Christmas Traditions & Historic Charm. Join an expert local guide for an optional walking tour through the city's holiday customs and history, with visits planned for the Doge's Palace, Venice's Old Prison, the Bridge of Sighs, Basilica San Marco and Piazza San Marco.
- Doge's Palace skip-the-line entrance and the seat of the historic Venetian Republic.
- The Old Prison and the Bridge of Sighs.
- Basilica San Marco, its Byzantine architecture and mosaics.
- The Campanile, Caffè Florian, Napoleon and the Winged Lion.
Venetian Gondola Experience. Before sunset, glide through Venice's canals with professional musicians adding to the atmosphere. The balance of the afternoon and evening is at leisure; your Tour Captain may invite you to an optional dinner and can assist with dining reservations.
What's Included
- Breakfast at your hotel
- Venetian gondola experience with musicians
- Tour Captain hosting and dining assistance
- Venice hotel accommodation
Chapter Two
Days 3–4
Florence
Fast rail brings the journey to Renaissance Florence for seasonal traditions, landmark piazzas and time to follow your own curiosity.
Renaissance stone, holiday light.
Florence balances guided context with open time, keeping the Duomo, markets, churches and evening streets close at hand.
03Day ThreeOnward to Florence
Included
Enjoy a relaxed morning, then boat to the Venice train station for the fast train to Florence while luggage is transferred separately. On arrival, walk to the centrally located hotels and freshen up.
Discovery Walk: Florence at Christmas Time. Explore Giotto's Bell Tower, the Baptistery, the Duomo, Orsanmichele Church and the Church of Via Santa Margherita while learning about Florentine holiday traditions.
The afternoon includes leisure time before an included Welcome to Florence Dinner hosted by your Tour Captain, with authentic Tuscan cuisine, premium beverages and local wines.
What's Included
- Breakfast at your hotel
- Boat transfer to the Venice train station
- Fast train to Florence and separate luggage transfer
- Tour Captain-led Florence Discovery Walk
- Welcome Dinner with wine and premium beverages
- Florence hotel accommodation
04Day FourChristmas Traditions in Florence
Included
Florence Christmas Traditions, Secrets & Treasures. Join your Tour Captain and local guide through the historic center, including the Duomo complex, Giotto's Bell Tower, the Baptistery's Gates of Paradise, Piazza della Repubblica, Piazza Signoria and the Uffizi portico.
- The Duomo complex: Santa Maria del Fiore, Baptistery and Campanile.
- Entrance to Orsanmichele, the former grain market transformed into a church.
- A walk through Florence's central piazzas and across the Ponte Vecchio.
The balance of the day is at leisure. Explore the leather market, inquire about climbing the Duomo, visit Santa Croce or enjoy the city at your own pace.
What's Included
- Breakfast at your hotel
- Florence Christmas Traditions guided experience
- Expert local guide and Tour Captain hosting
- Orsanmichele entrance as described
- Florence hotel accommodation
Chapter Three
Days 5–6
Tuscany
San Gimignano, a winery estate and Cortona's ancient lanes shift the journey into a slower, more rooted rhythm.
The road opens into the hills.
Tuscany brings together hill-town history, the table and the pleasure of leaving part of a day unscheduled.
05Day FiveGood Morning, Tuscany
Included
Travel into the Tuscan countryside and stop in hilltop San Gimignano, known for its medieval towers, Elsa Valley views and position along the historic Via Francigena. Enjoy time to explore its streets and shops.
Exclusive Winery Tasting with Morsels. Tour the production cellars at a winery estate, then taste Chianti and Super Tuscan varieties paired with farm-fresh pecorino, bruschetta and other local bites.
Continue along Tuscany's wine road to Cortona. After arriving and settling in, join a Discovery Walk along Via Nazionale to Piazza Garibaldi and Piazza della Repubblica, with stories of the Etruscans, Romans and the Battle of Lake Trasimeno.
The day concludes with an included Welcome Dinner in Tuscany hosted by your Tour Captain.
What's Included
- Breakfast at your hotel
- Transportation through San Gimignano to Cortona
- Winery estate and production-cellar tour
- Wine tasting with paired Tuscan specialties
- Tour Captain-led Cortona Discovery Walk
- Welcome Dinner and Cortona hotel accommodation
06Day SixCortona at Leisure
Enjoy a relaxing day in Cortona. This hill town above Lake Trasimeno is shaped by Etruscan history, 3,000-year-old walls and timeless views.
OptionalAsk about a cooking class, Siena day trip, horseback riding or Vespa rental, or simply explore ancient streets, hike toward the castle and stroll through the surrounding landscape.
In the evening, your Tour Captain may offer an optional dinner, or you can savor the final Cortona evening as you wish.
What's Included
- Breakfast at your hotel
- Tour Captain recommendations and assistance
- Cortona hotel accommodation
Final Chapter
Days 7–10
Rome
Old Rome, Vatican City, ancient landmarks and festive evenings lead toward the farewell dinner and the journey home.
Every era gathers in Rome.
The finale moves through ancient, Christian, Renaissance and present-day Rome while leaving meaningful room for personal choice.
07Day SevenOnward to Rome
Included
After breakfast, travel toward Rome and arrive at the hotel for check-in before the afternoon Discovery Walk.
Discovery Walk: Rome at Christmas Time. Walk through Old Rome amid holiday lights, Christmas trees and nativity scenes. Begin near Bernini's Elephant, step inside the Pantheon, cross Piazza Navona and Campo de' Fiori, then continue to Largo di Torre Argentina for the story of Julius Caesar and the modern Roman cat sanctuary.
The evening includes a Welcome to Rome Dinner hosted by your Tour Captain.
What's Included
- Breakfast at your hotel
- Planned transportation from Cortona to Rome
- Tour Captain-led Old Rome Discovery Walk
- Welcome to Rome Dinner
- Rome hotel accommodation
08Day EightRome & Vatican City
Optional · $185 per person
Consider an optional Vatican City tour featuring the Vatican Museums, the Sistine Chapel, St. Peter's Basilica and St. Peter's Square. Planned highlights include:
- St. Peter's Basilica and Square with guided touring and planned early admission.
- The Sistine Chapel and Michelangelo's Last Judgment.
- The Vatican Museums and their tapestries, sculpture and works of art.
Return transportation is planned near St. Peter's Square. The balance of the afternoon and evening is at leisure, with an optional dinner invitation from your Tour Captain.
What's Included
- Breakfast at your hotel
- Tour Captain hosting and local recommendations
- Rome hotel accommodation
09Day NineAncient Rome & Farewell
Enjoy a leisurely start with breakfast and time for the morning at your own pace.
Optional · $165 per personConsider a walking tour of ancient Rome with lunch. Planned views and stops include the Colosseum, Roman Forum, Capitoline Hill, Trajan's Market, Palatine Hill, the Curia, the Vittorio Emanuele II National Monument and the Jewish Ghetto.
IncludedFarewell to Rome Dinner. Join your Tour Captain to celebrate the lights, tastes, discoveries and new friendships of Italy at Christmas Time.
What's Included
- Breakfast at your hotel
- Farewell to Rome Dinner with your Tour Captain
- Wine and premium beverages with dinner
- Rome hotel accommodation
10Day TenArrivederci, Italy
Breakfast is included if your flight timing allows.
Departure transfer is optional and not included. Transfer from the Rome hotel to Rome Fiumicino Airport is $125 per person with a two-guest minimum; the price is $250 for a solo traveler.
Guests may also inquire about extending the vacation to the Amalfi Coast for two days and nights, including Pompeii and coastal experiences.
What's Included
- Breakfast at your hotel, flight timing permitting
What's Included
The details that make the journey effortless.
The inclusions below are drawn from the published Christmas itinerary; optional experiences remain clearly separate.
Your Tour Captain
Hosted throughout the journey, with Discovery Walks, destination orientation, recommendations and practical support.
9 hotel nights & breakfast
Nine breakfasts are included; departure-morning breakfast depends on flight timing.
Included dining
Five included dinners plus the Tuscany winery tasting and lunch experience described in the itinerary.
Planned transportation
Venice arrival meet-and-greet and water taxi, fast rail to Florence, luggage transfer and planned intercity transportation.
Discovery Walks
Tour Captain-hosted introductions in Venice, Florence, Cortona and Rome.
Venetian gondola
The included Venice gondola experience described on Day 2.
Tuscan winery experience
Estate admission, cellar touring, wine tasting and paired local specialties.
Included sightseeing
Itinerary-listed included touring and admissions, plus local guide services where specified.
Not included: international airfare, the optional Rome departure transfer, optional sightseeing and optional dining unless specifically stated otherwise.
Dates & Prices
Choose your holiday departure.
Prices are in USD per person, based on two guests per room. International airfare is not included.
First-to-Book Supplement: when you are the first guest to reserve a spot on a departure, a temporary supplement may be added so the journey can be guaranteed before the group forms. Once a second traveler confirms on the same departure, the supplement is removed from the final balance.
Private Journey: this route may also be offered for two guests with Venice arrival transfer, key sightseeing reservations, private guides and assistance at key moments, without hosted dinners or a Tour Captain. Inquire for details.
Private Journey: this route may also be offered for two guests with Venice arrival transfer, key sightseeing reservations, private guides and assistance at key moments, without hosted dinners or a Tour Captain. Inquire for details.
DELUXEThoughtfully selected 4- and 5-star hotels
CLASSICWell-located 3-star-plus hotels
2026 departures 10-day Venice to Rome
Dec 14–23, 2026
Deluxe$8,949
Classic$6,549
Inquire
Request a Journey Proposal
Dec 17–26, 2026
Deluxe$8,979
Classic$6,749
Inquire
Request a Journey Proposal
Dec 24, 2026–Jan 2, 2027
Pricing for this newly added departure is available from a Journey Designer.
New departure Request Pricing & Proposal2027 departures 10-day Venice to Rome
Dec 14–23, 2027
Deluxe$8,949
Classic$6,549
Inquire
Request a Journey Proposal
Dec 17–26, 2027
Deluxe$8,979
Classic$6,749
Inquire
Request a Journey Proposal
Not sure which departure is right?
A Journey Designer can compare timing, hotel collection and availability with you.
Your Home in Italy
Stay where the journey lives.
Properties are selected for location, character and comfort. Named hotels illustrate the collection and may be replaced with a comparable property.
Deluxe Hotels Collection
Thoughtfully selected 4- and 5-star hotels, including upgraded rooms at 4-star properties and refined entry-level rooms at 5-star stays. Ask about larger rooms, higher categories or specific views where available.
Classic Hotels Collection
Well-located 3-star-plus hotels featuring private bathrooms, air conditioning, continental breakfast and heart-of-the-city locations.
2 nights
Your Home in Venice
Hotel Saturnia & International, Hotel Monaco & Grand Canal or similar.
2 nights
Your Home in Florence
Grand Hotel Cavour, Hotel Bernini Palace or similar.
2 nights
Your Home in Cortona
Hotel Italia, Monastero Hotel & Spa or similar.
3 nights
Your Home in Rome
Palazzo Navona, Antico Albergo del Sole al Pantheon, Iconic Pantheon Rome Hotel, Hotel L'Orologio or similar.
Why Now Journey
Hosted, not herded.
The journey is deliberately small, personal and balanced between guided context and the freedom to experience Italy in your own way.
True small groups
Four to twelve guests is the expected group size, with a published maximum of sixteen.
Your Tour Captain
A dedicated host keeps transitions smooth, leads Discovery Walks and helps make the journey personal.
Thoughtful pacing
Guided experiences are balanced with afternoons and evenings at leisure.
Personal attention
Dining suggestions, optional experiences and practical questions are handled without a big-bus mentality.
Across Now Journey
50+ five-star guest reviews.
These reviews reflect the wider Now Journey experience and are not presented as reviews of this specific Christmas departure.
“I can't say enough about our recent trip to Italy. It was perfection from beginning to end.”Esther P., Now Journey guest
“We all were made to feel special, almost like royalty, with skip-the-line access, personal service by fabulous chefs, and seamless check-ins at our gorgeous hotels.”
Teresa C.“Our hotel accommodations were all perfect. Now Journey did an exceptional job planning and we even got surprises along the way.”
Tammy A.Frequently Asked Questions
The practical questions, answered.
Tour-specific details remain based on the published itinerary and existing Now Journey guidance.
How active is this journey?
The sightseeing pace is leisurely, with opportunities to stop or opt out. Existing Now Journey guidance says guests typically walk about 45 to 90 minutes per day during sightseeing.
How much leisure time is there?
The journey follows a slow-travel concept, with much of the guided sightseeing in the morning and meaningful afternoon or evening time at leisure.
How many guests travel together?
This tour is designed for four to twelve guests, with a published maximum of sixteen.
How do the hotel collections work?
Deluxe features thoughtfully selected 4- and 5-star hotels. Classic offers well-located 3-star-plus hotels. Exact properties remain subject to availability and comparable substitution.
Are the Vatican and ancient Rome tours included?
No. The Vatican City experience on Day 8 and the ancient Rome walking tour on Day 9 are clearly listed as optional and carry the published per-person prices shown in the itinerary.
What is not included?
International airfare, optional sightseeing, optional dining and the Rome airport departure transfer are not included unless specifically stated otherwise.
Begin the conversation
Italy feels different at Christmas.
Tell us which departure and hotel collection interest you. A Journey Designer will help with availability, pricing and the details that make the trip yours.
No obligation. No pressure. Personally reviewed proposals.
Venice's beauty was built on a maritime republic that connected Europe with the eastern Mediterranean for centuries. The Doge's Palace was not simply a residence: it was a center of government, justice and ceremony.
As you move between San Marco, the old prison and the Bridge of Sighs, notice how closely power, faith and commerce sit together. Winter quiet makes the relationship easier to see.
In Tuscany, wine, olive oil, cheese and bread are not decorative additions to the landscape. They are part of a long agricultural culture shaped by season, place and family production.
At the winery, listen for the relationship between the estate, the vintage and the food served beside it. Provenance here is a story as much as a label.
Rome rarely presents history in a neat sequence. Ancient columns, Renaissance palaces, Baroque fountains and modern streets remain physically in conversation.
Look for changes in street level, reused stone and fragments embedded in later buildings. Another Rome often survives directly beneath or within the one you see.