Itinerary
- Day 1
Arrival
You'll arrive in Rome whenever works for your flight. This evening there's a welcome briefing at the hotel where you'll meet your CEO and other travelers. Grab dinner with the group afterwards if you'd like, though it's optional.
Included Activities
- Welcome Moment - Meet Your CEO and Group
Optional Activities
- Dinner with group
- Day 2
Rome
Start the day on a migrant-led walking tour through Rome, then hop on public transit to Piazza Navona's Christmas market. The market sits on what used to be a 1st century stadium built by Domitian, and now it's filled with local handicrafts, toys, sweets, a carousel, and a Christmas tree. After browsing around, your CEO will walk with you from Navona toward Spagna, sharing stories about the neighborhoods and history along the way.
- Meals
- Breakfast
Included Activities
- Migrantour Rome
- Christmas Market Visit
Landmarks/POIs Piazza Navona Stadium of Domitian - Day 3
Rome to Montepulciano
Take a train out of Rome, then transfer to Pienza where you'll have time to walk around and get a feel for the town. Continue on to Montepulciano in the Tuscan countryside. Your CEO will give you an orientation walk, then you'll do a local wine tasting. This area's known for its pork, cheese, Pici pasta, honey, and wine production. If the Christmas market is operating, you can check it out too.
- Meals
- Breakfast
Included Activities
- Orientation Walk Pienza
Optional Activities
- Montepulciano Wine Tasting
- Montepulciano Christmas Market (if operating)
Landmarks/POIs Pienza Montepulciano - Day 4
Montepulciano
Spend your entire day in the Tuscan wine region with options depending on what interests you. Choose a vineyard tour with wine tasting, a bike ride through the rolling hills, or a trip to the thermal springs at Bagni San Filippo. It's your day to explore however you want.
- Meals
- Breakfast
Optional Activities
- Vineyard tour and wine tasting
- Bike ride in the rolling hills
- Bagni San Filippo Thermal Springs visit
Landmarks/POIs Bagni San Filippo - Day 5
Montepulciano to Florence
Head to Siena for an orientation walk with your CEO. You can optionally visit Torre del Mangia, the Battistero, il Campo, or the Duomo, or just take a leisurely walk around to meet locals. Later, travel to Florence and spend your evening walking up to Piazzale Michelangelo for views over the city. On the way you'll pass through the Mercato di Natale Firenze Christmas Market.
- Meals
- Breakfast
Included Activities
- Orientation Walk Siena
- Christmas Market Visit
- Piazzale Michelangelo Walk
Optional Activities
- Torre del Mangia visit
- Battistero visit
- Il Campo visit
- Duomo visit
- Passeggiata with locals
Landmarks/POIs Siena Piazzale Michelangelo Mercato di Natale Firenze Piazza Santa Croce Basilica di Santa Croce - Day 6
Florence
Join a guided walking tour through Florence this morning where you'll learn about the city's history and local culture. The afternoon is completely yours to use as you wish. You might visit the Duomo, see Michelangelo's David at the Galleria dell'Accademia, check out the Uffizi Gallery, walk across Ponte Vecchio, explore the Medici Chapels, or take a wine tasting bike tour toward Fiesole and the Chianti vineyards. Mercato Centrale has food stalls, and the city is filled with cafes and trattorias.
- Meals
- Breakfast
Included Activities
- Florence Guided Walking Tour
- Florence Market and Food Tour
Optional Activities
- Duomo visit
- David at Galleria dell'Accademia visit
- Uffizi Gallery visit
- Ponte Vecchio visit
- Medici Chapels visit
- Wine tasting bike tour to Fiesole and Chianti vineyards
- Mercato Centrale exploration
Landmarks/POIs Duomo Galleria dell'Accademia Uffizi Gallery Ponte Vecchio Medici Chapels Fiesole Chianti Mercato Centrale - Day 7
Florence to Venice
Travel to Venice by train and watch the scenery change as you head north. After checking into your hotel, a guided walking tour takes you through the city's main areas and highlights. Then you'll have time to explore the local Christmas market on your own. Your evening is free, though your CEO can recommend a spot for an optional group dinner at a restaurant they know well.
- Meals
- Breakfast
Included Activities
- Guided Walking Tour of Venice
- Christmas Market Visit
Optional Activities
- Dinner with group
Landmarks/POIs Venice San Marco Santa Chiara church Bridge of Sighs Doge's Palace - Day 8
Venice
You have the full day to experience Venice however you'd like. Wander the Christmas markets, take a gondola ride, or simply walk through the canals and the confusing maze of streets. The city has museums and historic architecture everywhere you look. Consider doing a food tour of the local culinary scene if that sounds good. Later in the evening, you can join the group for an optional final dinner together.
- Meals
- Breakfast
Optional Activities
- Food tour
- Gondola ride
- Final dinner with group
Landmarks/POIs Venice Christmas Markets - Day 9
Departure
Depart Venice whenever suits your travel plans.
- Meals
- Breakfast











