Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Visiting Pisa’s Piazza dei Miracoli and the Leaning Tower

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

Explore Tuscany's highlights on a full-day tour visiting Pisa, Siena, San Gimignano, and Chianti, with wine tasting, in about 12 hours from Florence.

This Tuscany day trip offers a comprehensive taste of some of Italy’s most iconic towns for just $77.02 per person. Starting early from Florence, the tour takes approximately 12 hours, guided by a professional team in a modern, air-conditioned bus. You’ll visit Pisa, marvel at the Leaning Tower, explore Siena’s medieval streets, enjoy a Tuscan lunch with four wines, and wander through San Gimignano’s famous towers.

While the tour is praised for its knowledgeable guides, stunning scenery, and the inclusion of wine tasting, it’s worth noting that walking distances can be significant, especially at some stops. Those with mobility issues or seeking more time at each site might find the schedule a little rushed. This tour stands out as a great option for those wanting to see multiple towns in one day without the hassle of driving.

Key Points

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Key Points

  • Full-day trip from Florence covering Pisa, Siena, San Gimignano, and Chianti
  • Price of $77.02 includes transportation, guide, lunch, and wine tasting**
  • Guided walking tour of Siena with entrance to the Siena Cathedral**
  • Visit Pisa’s Piazza dei Miracoli, including the Leaning Tower and Duomo (entry fees not included)**
  • Lunch at a family-run winery with four local wines and free time in San Gimignano
  • Comfortable transport with earphones for guided commentary during Siena tour**
  • Maximum of 50 travelers, making it suitable for small groups**
  • Some walking required, with potential challenges for those with mobility issues**

Starting Point and Departure Details in Florence

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Starting Point and Departure Details in Florence

The tour begins at Piazzale Montelungo in Florence at 7:30 am. The coach is modern and air-conditioned, designed to keep travelers comfortable throughout the long day. This early start ensures you arrive in Siena early enough to enjoy the town as it wakes up, making the most of your guided walking tour.

The return to Florence is included in the schedule, and the tour ends back at the departure point, giving you the convenience of easy access to your accommodations or other activities.

Visiting Pisa’s Piazza dei Miracoli and the Leaning Tower

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Visiting Pisa’s Piazza dei Miracoli and the Leaning Tower

The first stop is Pisa, where you disembark at the Field of Miracles. Here, you see the famous Leaning Tower of Pisa, standing nearly 56 meters tall with a lean of about 4 degrees. This site, a UNESCO World Heritage site, features Romanesque architecture, including the Duomo and Baptistery.

The piazza is a great spot for photos, and while these buildings are free to view from outside, entry to the Duomo and Baptistery requires separate tickets, which are not included. Expect around 15 minutes at each location, balancing sightseeing with enough time for photos.

The city walls and the Camposanto Monumentale are also nearby, offering a glimpse into Pisa’s medieval defenses and historic cemetery, though these are not part of the official stops.

Exploring Pisa’s Cathedral and Baptistery

The Duomo di Pisa, known as the Cathedral of Santa Maria Assunta, is a highlight with its marble facades and artwork inside, including pulpit sculptures by Giovanni Pisano. The Baptistery is noted for its Romanesque and Gothic architecture and its round shape, surrounded by columned arcades.

While entry fees are not included, visitors typically spend about 10 minutes at each. The Baptistery’s architecture complements the cathedral, adding to the impressive atmosphere of the Piazza dei Miracoli.

The Iconic Leaning Tower of Pisa

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - The Iconic Leaning Tower of Pisa

No visit to Pisa is complete without a look at the leaning tower. Standing around 56 meters tall, it leans at about 4 degrees, making it one of the most famous buildings in the world. Visitors are free to wander nearby, take creative photos, or simply marvel at its tilt.

The visit duration is approximately 15 minutes, and tickets to climb the tower are not included. While the tour does not include going up the tower, many still enjoy the experience of being in this world-renowned monument.

Traveling through Chianti to San Gimignano

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Traveling through Chianti to San Gimignano

After Pisa, the tour continues through the Chianti countryside, renowned for its vineyards and rolling hills. The drive offers beautiful views and a chance to enjoy the landscape from the comfort of the bus.

Next, the group arrives at San Gimignano, famous for its medieval skyline with tall, narrow towers. The town’s UNESCO World Heritage status and well-preserved town plan make it a highlight.

A lunch with four local wines at a family-run winery is included, where guests can savor traditional Tuscan dishes paired with local wines. Afterward, there’s free time to explore Piazza della Cisterna, a triangular square surrounded by medieval towers and historic buildings.

Discovering San Gimignano’s Medieval Charm

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Discovering San Gimignano’s Medieval Charm

Post-lunch, visitors have about 30 minutes to discover San Gimignano independently. The town’s walls, dating from the 13th century, are among the best-preserved in Italy. A walk along these walls offers panoramic views of the town and the surrounding Tuscan landscape.

The Piazza della Cisterna is the focal point of the town, lined with medieval shops and cafés. Its architecture, combined with the tower skyline, creates a unique medieval cityscape reminiscent of a “Manhattan of the Middle Ages”.

Arriving in Siena: The Hilltop Beauty

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Arriving in Siena: The Hilltop Beauty

The last major stop is Siena, a hilltop city with a fascinating pedestrianized historic center. The town’s famous monuments include the Piazza del Campo and the Siena Cathedral.

A guided walking tour leads through the town’s narrow streets, passing the world’s oldest bank, Monte dei Paschi at Piazza Salimbeni, and the beautiful Piazza del Campo. The cathedral features remarkable artworks by Donatello and Michelangelo, with optional entry included if the cathedral visit is selected.

The Torre del Mangia, standing 87 meters tall, offers spectacular views of Siena and the surrounding countryside. Visitors can admire the medieval architecture and local art during their stroll.

Practical Details and Accessibility

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Practical Details and Accessibility

The tour includes transportation in a modern bus, with earphones provided during the Siena guided tour for better listening. Comfortable shoes are recommended, as some walking and short climbs are involved. The meeting point is near public transportation in Florence, and early arrival is essential.

Physical fitness should be moderate, given the walking distances and hilly terrain, especially at Siena and Pisa. The tour’s schedule is tight to maximize sightseeing, meaning some stops might feel rushed, especially for visitors with mobility challenges.

Final Thoughts on the Tuscany Day Trip

This full-day tour offers a well-rounded experience of Tuscany’s most famous towns, packed with sightseeing, historical landmarks, and tasting local wines. The guides are frequently praised for their knowledge and friendliness, and the scenery along the drive is a highlight.

Limitations include limited time at each stop, which might leave some visitors wishing for more in-depth exploration. The walking distances can be demanding, and entry fees for sites like the Pisa Cathedral and tower are not included.

This tour suits those who want to cover a lot of ground in one day without driving, and who are comfortable with moderate physical activity. It delivers a balanced blend of cultural sights, scenery, and local cuisine, making it a good choice for first-timers or travelers wanting a comprehensive Tuscany experience.

✨ Book This Experience

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti



4.5

83% 5-star

“The guides were the best part of the tour-they were very informative and polite. The sites were beautiful. You wont regret booking this tour. Overa…”

— Rafael D, Featured

Frequently Asked Questions

Does the tour include entry to Pisa’s Leaning Tower?
No, tickets to climb the tower are not included. You can view the tower from outside and take photos.

Is lunch included in the price?
Yes, the lunch at a family-run winery with four wine tastings is part of the package, unless you select the without lunch option.

How much walking should I expect?
Some walking is required, especially in Siena and Pisa. The tour involves short walks from parking areas to the attractions, which might be challenging for those with mobility issues.

Can I visit the Siena Cathedral?
Yes, the cathedral is included if the option is selected, and features stunning artwork and architecture.

What is the best way to prepare for this tour?
Wearing comfortable shoes is recommended, and bringing original ID is necessary for site visits. Be mindful of moderate physical fitness requirements.

Can I cancel this tour?
Yes, free cancellation is available up to 24 hours before the start time for a full refund.

Who operates this tour?
The experience is provided by CAF Tour and Travel.
For more details, contact +39055283200 or email [email protected].