Itinerary
- Day 1
Florence
You'll arrive in Florence at your own pace, giving you the rest of the day to get settled and wander around however you like. The city's yours to explore on your schedule. You're staying for 2 nights in Florence or the surrounding area, so there's no rush to see everything today.
Optional Activities
- Explore Florence at leisure
- Day 2
Florence
You'll spend the day moving through Florence's art and architecture. Start with Santa Croce, then head to Palazzo Vecchio to see the replica of Michelangelo's David. The Baptistery of San Giovanni is nearby and worth a look, along with Palazzo Medici-Ricardi. If you want to dive deeper into art, the Uffizi Gallery has extensive European paintings from various periods. Otherwise, wandering through the city center works just fine too, and you can grab coffee at a cafe in Piazza della Repubblica to rest your feet. For dinner, find a local restaurant and try some typical Tuscan food.
- Meals
- Breakfast, Dinner (Typical Tuscan dinner in a restaurant in Florence (excluding drinks))
Included Activities
- Visit Santa Croce, the largest Franciscan church in Italy
- Visit Palazzo Vecchio in Piazza della Signoria
- Visit the octagonal baptistery of San Giovanni
- Visit Palazzo Medici-Ricardi
Optional Activities
- Visit the Uffizi Gallery for European paintings from 13th to 18th centuries
- Stroll through the alleyways of the city center
- Relax at a café in Piazza della Repubblica
Landmarks Santa Croce Palazzo Vecchio Piazza della Signoria San Giovanni (Baptistery) Palazzo Medici-Ricardi Uffizi Gallery Piazza della Repubblica - Day 3
San Gimignano
Head through the Tuscan landscape with its rolling hills, vineyards, and olive groves on your way to San Gimignano. Once you arrive, walk through the medieval town and check out its famous towers, then pop into the Basilica of Santa Maria Assunta. You'll have time to wander through Piazza della Cisterna and grab gelato from one of the local gelateries in the central piazza. You're staying for 3 nights in the San Gimignano or Siena area.
- Meals
- Breakfast
- Accommodation
- Hotel
Included Activities
- Visit Basilica of Santa Maria Assunta
- Explore Palazzo del Popolo with Civic Museum
- Explore Piazza della Cisterna
- Taste ice cream in gelateria at Piazza della Cisterna
Landmarks Basilica of Santa Maria Assunta Palazzo del Popolo Piazza della Cisterna 
- Day 4
Volterra - Certaldo
Start in the ancient Etruscan town of Volterra, which sits at about 1,640 feet up on a hill. You'll see remnants of city walls from the 3rd-4th century AD and what's left of the Roman amphitheater. Stop by the cathedral and Piazza dei Priori to see the bishop's palace and Pretorio Palace, then spend time at the Guarnacci Museum checking out Etruscan alabaster ash urns. After that, head to Certaldo and take the funicular up to explore the medieval old town, Palazzo Pretorio castle, and the museum dedicated to writer Giovanni Boccaccio.
- Meals
- Breakfast
Included Activities
- Explore Volterra city walls and Roman amphitheater remains
- Visit Volterra Cathedral
- Explore Piazza dei Priori with bishop's palace and Pretorio Palace
- Visit Guarnacci Museum to see Etruscan alabaster ash urns
- Take funicular to upper town of Certaldo
- Explore medieval Certaldo old town
- Visit Palazzo Pretorio in Certaldo
- Visit Giovanni Boccaccio Museum
Landmarks Volterra City Walls Roman Amphitheater, Volterra Volterra Cathedral Piazza dei Priori Palazzo Pretorio, Volterra Guarnacci Museum Palazzo Pretorio, Certaldo Giovanni Boccaccio Museum 
- Day 5
Siena - Monteriggioni
Drive to Siena and try some traditional Christmas pastries in the city center. The afternoon is for exploring this Gothic city with its winding medieval streets and red-brown brick palaces. You can visit the Palazzo Pubblico and climb Torre del Mangia to get views over Piazza del Campo. From there, head to Monteriggioni, one of Italy's best-preserved medieval town centers. It's surrounded by nearly 2,000 feet of city walls, and you can walk through the historic gates while taking in views of the Tuscan countryside.
- Meals
- Breakfast
Included Activities
- Taste traditional Christmas pastries in Siena
- Visit Palazzo Pubblico
- Climb Torre del Mangia
- Explore Piazza del Campo
- Explore Monteriggioni medieval town center
- Visit Porta Fiorentina (North Gate) in Monteriggioni
- Visit Porta Romana / Porta San Giovanni (South Gate) in Monteriggioni
Optional Activities
- Explore Siena at leisure
Landmarks Palazzo Pubblico Torre del Mangia Piazza del Campo Monteriggioni Porta Fiorentina Porta Romana - Day 6
Pisa - Montecarlo
Visit Pisa to see the famous Leaning Tower and the Square of Miracles with its cathedral, baptistry, and cemetery. Go inside the Cathedral of Santa Maria Assunta to check out the hexagonal pulpit in the Baptistry. Then head to Montecarlo, a well-known wine region in the Lucca plain. The old town sits on a solitary hill, and you'll see the fortress built by Cosimo I de' Medici, the church of S. Andrea, the historic chapel of St. Anna, and the 18th century Teatro dei Rassicurati opera house. You're staying for 2 nights in Pisa or the surrounding area.
- Meals
- Breakfast
- Accommodation
- Hotel
Included Activities
- Visit Leaning Tower of Pisa
- Explore Cathedral of Santa Maria Assunta
- Explore Baptistry with hexagonal pulpit by Nicola Pisano
- Explore Camposanto cemetery
- Visit Montecarlo fortress
- Visit Church of S. Andrea in Montecarlo
- Visit Chapel of St. Anna in Montecarlo
- Visit Teatro dei Rassicurati opera house
Landmarks Leaning Tower of Pisa Cathedral of Santa Maria Assunta Baptistry of Pisa Camposanto Montecarlo Fortress Church of S. Andrea Chapel of St. Anna Teatro dei Rassicurati - Day 7
Lucca
Travel to Lucca, known as the city of a hundred churches. It's surrounded by a medieval city wall, and you can enter through one of seven historic gates. Walk through the charming historic center, which covers about half a square mile. Stop at the market square (originally a Roman amphitheater) and visit Piazza San Michele to see the magnificent San Michele in Foro church and Palazzo Pretorio. Later, you can do wine tasting at your hotel or head out to a winery in Montecarlo.
- Meals
- Breakfast
Included Activities
- Explore Lucca historic center
- Visit market square (former Roman amphitheater)
- Explore Piazza San Michele
- Visit Church of San Michele in Foro
- Explore Palazzo Pretorio in Lucca
- Wine tasting at hotel or at winery in Montecarlo
Landmarks Lucca City Wall Piazza San Michele San Michele in Foro Palazzo Pretorio, Lucca Lucca Market Square - Day 8
Florence
After checking out of your hotel, you'll head back on your own. The timing depends on your departure, so plan accordingly based on your travel arrangements.
- Meals
- Breakfast
