Siena, San Gimignano, Pisa, and a Chianti wine estate in one day. This full-day tour from Florence covers the four most iconic Tuscan destinations with a guide, air-conditioned coach, winery lunch with wine tasting, and entry to Siena’s cathedral included. Return to Florence by 8:30 PM with 20,000 steps and a camera full of photos.
Tour Details and Price (2026)
Tuscany Day Trip: Siena, San Gimignano, Pisa and Lunch at a Winery
- From $90 per person (currently 20% off, regular price $112)
- 12-hour full day tour departing from Florence
- Professional English-speaking guide for the entire day
- Air-conditioned coach
- Guided walking tour of Siena with entry to the cathedral
- Farmhouse lunch with wine tasting (4 wines) at an organic family-run estate in Chianti
- Free time to explore San Gimignano and Pisa at your own pace
- Optional upgrade: tickets to climb the Leaning Tower of Pisa
- 4.9 stars from 22,400+ reviews, 98% recommendation
- Winner of the 2025 Viator Experience Award
- Operated by Walkabout Florence Tours
👉 Book your Tuscany day trip from Florence
What You’ll See
Siena (1.5 hours + free time). Guided walking tour through the medieval city. Your guide takes you through the Contrada districts (Siena’s rival neighborhoods that compete in the famous Palio horse race), into Piazza del Campo (one of Europe’s most striking public squares), and inside Siena’s black-and-white marble cathedral.
Chianti winery lunch (2 hours). The highlight for most travelers. A relaxed lunch at an organic family-run wine estate in the Chianti hills. Tuscan menu includes fettunta with olive oil, pasta with Chianina beef ragù, cured meats, local cheeses, and biscotti with Vin Santo dessert wine. Four wine tastings: Vernaccia, Chianti, Chianti Classico Riserva, and Vin Santo. Vegetarian and gluten-free options available.
San Gimignano (1.5 hours). Free time in the “Medieval Manhattan,” a UNESCO hill town famous for its ancient towers and stunning views over the Tuscan countryside. Tip from reviewers: try the gelato at Dondoli in the main square.
Pisa (1.25 hours). Visit Piazza dei Miracoli to see the Leaning Tower, the Cathedral, and the Baptistery. Upgrade option available to climb the tower (book in advance, as time slots sell out).
Meeting Point
Check in at 7:45 AM at Piazza della Stazione 27, Florence. Your guide will be holding a “Walkabout Tours” sign by the taxi stand at Santa Maria Novella train station, across from the outdoor McDonald’s.
Before You Book
- Lots of walking. Expect 15,000 to 20,000 steps across uneven cobblestone streets and hills. Comfortable shoes are essential. Not suitable for travelers with walking difficulties or wheelchairs.
- Leaning Tower of Pisa. Not included in the base ticket. Select the upgrade at booking to guarantee your climb slot. Children under 8 are not admitted. Ages 8 to 18 must be accompanied by an adult.
- Siena cathedral alternative. If the Duomo is closed for religious services, you visit Palazzo delle Papesse instead.
- Weather. Tour operates rain or shine. Bring layers and an umbrella. Tuscan weather can change multiple times in a day.
- No food on the bus. Only water is allowed. Eat breakfast before check-in.
- Return to Florence. Approximately 8:30 PM. If booking onward train travel, schedule departures after 9:00 PM to allow for potential traffic delays.
- Cancellation: free cancellation up to 24 hours in advance for a full refund.
Book Your Tuscany Day Trip
4.9 stars from 22,400+ reviews and a Viator Experience Award. Four Tuscan destinations, a winery lunch, wine tasting, and a guide who makes it all effortless. From $90 per person.
👉 Check availability and book your tour
Prices based on 2026 rates. The 20% discount is available until July 1, 2026. Confirm final price at checkout.
