Itinerary
- Day 1
Florence
You'll arrive at Florence airport and pick up your rental car for the drive to your hotel. Once you've checked in, head out to wander through Florence's historic streets. The Arno River and Ponte Vecchio are right there to explore, so you'll get a feel for the city on your first evening.
- Start point
- Aeroporto di Firenze Amerigo Vespucci (FLR), Via del Termine, 11, Firenze, Florence 50127, Italy (Car pick up at Florence Airport)
- Accommodation
- Hotel (Grand Hotel Adriatico)
Optional Activities
- Wander through the oldest streets of Florence
- Walk along the Arno River
- Explore Ponte Vecchio
Landmarks/POIs Arno River Ponte Vecchio 
- Day 2
Florence
Start with breakfast at the hotel, then make your way to the Accademia Gallery to see Michelangelo's David along with his other sculptures. You'll have free time during the day to walk around Florence and grab lunch wherever looks good. In the afternoon, head to Piazza del Duomo to see Brunelleschi's Dome and the Baptistery's Gates of Paradise. After that, spend time at the Uffizi Gallery looking at works by Botticelli, Leonardo da Vinci, Michelangelo, and Raphael.
- Meals
- Breakfast (Breakfast at the hotel)
- Accommodation
- Hotel (Grand Hotel Adriatico)
Included Activities
- Visit Accademia Gallery with Michelangelo's David
- Visit Uffizi Gallery
Optional Activities
- Wander Florence's charming streets
- Enjoy local lunch
- Admire Brunelleschi's Dome
- View the Baptistery's Gates of Paradise in Piazza del Duomo
- Explore Uffizi Courtyard
- Stroll through Ponte Vecchio
Landmarks/POIs Accademia Gallery (Galleria dell'Accademia) Uffizi Gallery (Galleria degli Uffizi) Piazza del Duomo Brunelleschi's Dome (Florence Cathedral Dome) Baptistery of Florence Ponte Vecchio 
- Day 3
Florence to Pisa
After breakfast, you'll drive to Pisa to see its famous monuments. Piazza dei Miracoli, a UNESCO World Heritage Site, is where you'll find the Leaning Tower along with the Cathedral and Monumental Cemetery. If you want to go inside the Cathedral, check what's available that day. Take some photos and learn about Pisa's history before heading back to Florence for the night.
- Meals
- Breakfast (Breakfast at the hotel)
- Accommodation
- Hotel (Grand Hotel Adriatico)
Optional Activities
- Admire exterior of the Leaning Tower
- View the Cathedral exterior
- Explore the Monumental Cemetery exterior
- Explore Cathedral interiors (if available)
- Take photos of Piazza dei Miracoli
- Learn about Scuola Normale Superiore
Landmarks/POIs Leaning Tower of Pisa (Torre Pendente) Piazza dei Miracoli Pisa Cathedral (Cattedrale Metropolitana di Pisa) Monumental Cemetery (Camposanto Monumentale) 
- Day 4
Florence to Chianti
You'll have breakfast and check out, then drive into the Chianti region, one of Italy's top wine areas. The Chiantigiana wine route takes you through rolling vineyards and olive groves. Stop in a typical Chianti village to look around local shops, then head to a winery for your included wine tasting and light lunch. From there, you'll drive to your new hotel in Gaiole in Chianti.
- Meals
- Breakfast (Breakfast at the hotel), Lunch (Wine tasting and light lunch in a local winery)
- Accommodation
- Hotel (Hotel Le Pozze di Lecchi)
Included Activities
- Wine tasting and light lunch in a local winery of the Chianti area
Optional Activities
- Explore typical Chianti village
- Shop at gourmet or souvenir shops
Landmarks/POIs Chiantigiana Wine Route Greve in Chianti - Day 5
Gaiole in Chianti
This day is yours to spend however you like in the Chianti area. You've got your rental car, so you can explore the region at your own pace and check out whatever interests you most.
- Meals
- Breakfast (Breakfast at the hotel)
- Accommodation
- Hotel (Hotel Le Pozze di Lecchi)
Optional Activities
- Explore the Chianti area independently
- Day 6
Chianti - Siena - San Gimignano
After breakfast, drive to Siena to explore this powerful Renaissance city-state. Walk from Salimbeni Square, which has Europe's oldest bank, over to the impressive Gothic Duomo. Make sure to visit Piazza del Campo, one of the world's most famous squares with its distinctive shell shape and history as the venue for the Palio horse race. Then it's a 45-minute drive to San Gimignano, a UNESCO World Heritage medieval village sitting on a Tuscan hillside, known for its 13th-century walls and stone towers. Grab some of San Gimignano's well-known gelato before returning to Gaiole in Chianti.
- Meals
- Breakfast (Breakfast at the hotel)
- Accommodation
- Hotel (Hotel Le Pozze di Lecchi)
Optional Activities
- Walk from Salimbeni Square to the Duomo of Siena
- Visit Piazza del Campo
- Explore medieval buildings in San Gimignano
- Walk San Gimignano's medieval streets
- Visit San Gimignano's gelaterias
- Learn about Vernaccia di San Gimignano white wine
Landmarks/POIs Salimbeni Square (Piazza Salimbeni) Siena Cathedral (Cattedrale Metropolitana di Siena) Piazza del Campo San Gimignano 
- Day 7
Gaiole in Chianti to Florence Airport
You'll have breakfast at the hotel and take it easy in the morning. In the afternoon, return your rental car at the car hire office at Florence airport and wrap up your tour.
- Meals
- Breakfast (Breakfast at the hotel)
Optional Activities
- Free time in Gaiole in Chianti or surrounding area
