Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa & Winery Lunch

Overview

Experience the best of Tuscany in a single day on this guided tour from Florence. Explore the medieval streets of Siena, marvel at its Gothic cathedral, stroll through the UNESCO-listed hill town of San Gimignano, and visit Pisa’s iconic Leaning Tower. Immerse yourself in the Tuscan countryside, with the option to enjoy hearty lunch and wine tasting at a family-run estate in the Chianti region.

This all-in-one Tuscany experience is ideal for travelers seeking culture, history, food, and stunning scenery—all in one seamless itinerary.

Highlights:

• Explore Siena with a guided walking tour, including Siena Cathedral

• Wander the charming streets of San Gimignano, the medieval “Town of Towers”

• Admire Piazza dei Miracoli and the Leaning Tower of Pisa (optional climb)

• Enjoy Chianti countryside views, with optional lunch and wine tasting

• Small-group experience ensures personalized attention

What’s Included

• Air-conditioned vehicle for the day

• Professional English-speaking tour guide

• Guided walking tour of Siena, including cathedral entry

• Hearty farmhouse lunch with vegetarian options

• Wine tasting of four local varieties

• Free time to explore San Gimignano and Pisa

• Hotel pickup and drop-off

• Personal radio headset (if needed)

• Gratuities

Not included: Optional climb of the Leaning Tower of Pisa (upgrade available)

Meeting Point & Timing

Meeting Point: Piazza della Stazione, 27, 50123 Florence, FI, Italy
Instructions: Check in at 7:45 AM. Look for your guide holding a WALKABOUT TOURS sign near the taxi stand at Santa Maria Novella train station, across from the McDonald’s.
Tour Ends: Back at the same meeting point in Florence

Detailed Itinerary

1. Florence – 15 minutes

Meet your guide in front of Santa Maria Novella station and board the comfortable coach for your Tuscan adventure.

2. Siena – 3 hours

Travel to Siena, a stunning medieval hill town. Enjoy a guided walking tour, exploring Piazza del Campo, Contrada della Torre, and the historic Palazzo Salimbeni, home to the oldest bank in the world.

3. Duomo di Siena – 15 minutes

Visit the magnificent Siena Cathedral, a Gothic masterpiece with intricate marble floors, frescoes, and sculptures.

4. Chianti Wine Estate – 1.5 hours

Drive through the picturesque Tuscan hills to Fattoria Poggio Alloro, an organic family-run winery. Savor a hearty farmhouse lunch and taste four varieties of local Chianti wine.

5. San Gimignano – 1.5 hours

Stroll through this UNESCO World Heritage Site, known for its medieval towers. Visit Piazza della Cisterna and Piazza del Duomo, and enjoy panoramic views from Rocca of Montestaffoli.

6. Pisa – 1.5 hours

Travel through rolling Tuscan countryside to Pisa. Explore Piazza dei Miracoli and, if selected, climb the Leaning Tower of Pisa for breathtaking views of the square.

7. Return to Florence – 1 hour

Relax on the scenic drive back to Florence, returning with memories, photos, and a taste of authentic Tuscan life.

Additional Information

• Confirmation received at booking

• Not wheelchair accessible; moderate fitness required

• Vegetarian lunch available; gluten-free and other dietary restrictions not accommodated

• Infants must sit on laps

• Tour operates in all weather; dress appropriately

• Recommended: plan train travel after 9 PM to allow for traffic delays

Book your Tuscany day trip today and experience the medieval cities, rolling vineyards, iconic monuments, and authentic cuisine that make this region of Italy unforgettable.