Siena, Pisa & San Gimignano Tour with Lunch and Wine Tasting

Exploring Tuscany in a Day: Siena, Pisa & San Gimignano with Lunch and Wine Tasting

Taking a full-day tour through Tuscany sounds like a dream, but how much can you really see in just over 11 hours? This small-group journey from Florence offers an engaging way to tick off some of the region’s most iconic spots — Siena, Pisa, and San Gimignano — all with the added bonus of wine tastings and a traditional Tuscan lunch. It’s a busy day, but one packed with authentic experiences and picturesque moments that make it worth every penny.

What makes this tour particularly appealing? First, the intimate group size of no more than 25 guests ensures you won’t feel lost in a crowd. Second, the combination of sightseeing, gourmet food, and wine delivers a well-rounded taste of Tuscany’s culinary and cultural richness. Third, the free time in Pisa and San Gimignano means you can explore at your own pace, not just follow a guide with a stopwatch. The potential downside? The packed schedule might be a bit rushed for those wanting a more relaxed pace or deeper exploration of each city. Still, if you’re eager to see a lot without the hassle of planning, this tour offers excellent value.

This experience is a great fit for travelers who love history, good food, and wine, and don’t mind a long day on the road. It’s especially suited for those who want to maximize their time in Tuscany without missing the main sights, while enjoying some authentic regional flavors along the way.

Good To Know

• Intimate group size for a more personalized experience
• All-inclusive with lunch and wine tastings, offering good value
• Flexible free time to explore Pisa and San Gimignano independently
• Comfortable transportation with Wi-Fi provided
• Expert guides offering insights into Tuscan culture and history
• Entry tickets to Siena Cathedral included

You can check if your dates are available here:

A Detailed Look at the Tour Itinerary

Starting Point and Transportation

The tour kicks off at the Tours & News KIOSK at Piazzale Montelungo in Florence, next to Santa Maria Novella Train Station. Expect a prompt departure in a comfortable, air-conditioned minibus or minivan complete with free Wi-Fi — a bonus for those who want to share photos or catch up on messages during the scenic drive. The small group size means you’re not lost among dozens of travelers, allowing for easier interactions with your guide and fellow travelers.

Morning in Siena: Medieval Charm and Architectural Marvels

After about an hour of driving through the rolling hills of the Chianti region, you’ll arrive in Siena, a town that feels like stepping back in time. Your local guide will lead a 1-hour tour around the Piazza del Campo, famous for its shell-shaped design and medieval vibe. Expect to hear fascinating stories about Siena’s past as a rival city-state, and see key landmarks that define its character.

Next, you’ll visit the Siena Cathedral, one of Italy’s most beautiful Gothic structures. Entrance is included, giving you access to its stunning interior decorations and artworks. Keep in mind, Siena Cathedral has a strict dress code — shoulders and knees should be covered — so plan accordingly. Reviewers mention that the interior is “even more breathtaking than the outside” and that exploring it is time well spent.

Mid-Morning Coffee and Free Exploration

After the guided part of Siena, you’ll have time to wander on your own. Whether you prefer to sip an espresso in a cozy café or browse local shops, this break offers a nice balance to the structured tour. Some travelers note that Siena’s charming streets are “full of artisan shops and quaint corners that are perfect for photos.”

More Great Thing To Do Nearby

Lunch and Wine Tasting at a Tuscan Estate

Post-Siena, the journey continues to a family-run wine estate in the countryside. Here, you’ll indulge in a delicious three-course lunch featuring regional ingredients, complemented by expertly paired wines. The lunch offers a true taste of Tuscany, with fresh appetizers, pasta, and desserts. Reviewers emphasize the quality and authenticity of the meal, often calling it a highlight of the day.

This stop also provides a wine tasting that showcases local varieties, often described as “delicious” and “well-selected.” The setting itself, offering panoramic views, adds to the sensory experience. Some guests mention the chance to buy bottles directly from the estate, which makes this stop not only enjoyable but also practical for bringing home a piece of Tuscany.

Afternoon in San Gimignano: The Medieval Manhattan

Fortified and inspired, the tour swings toward San Gimignano, a UNESCO World Heritage Site. Known as the “Manhattan of the Middle Ages” due to its towering skyline, this hilltop town is a photographer’s paradise. Wander through narrow cobbled streets, admire the medieval towers, and browse artisan shops offering local crafts and souvenirs.

Many reviews highlight how stunning the panoramic views are from the town’s vantage points, perfect for photos. You’ll have free time here, so whether you choose to indulge in a gelato, visit a small museum, or simply soak up the atmosphere, the choice is yours. Travelers appreciate that the free time allows for personalized exploration beyond the typical tourist spots.

Late Afternoon in Pisa: The Iconic Leaning Tower

The last stop is Pisa, home to the famous Leaning Tower. The guided tour takes you around the Piazza dei Miracoli, where you can marvel at the Cathedral and Baptistery — both fine examples of Romanesque architecture. Entrance to these sites isn’t included, but the exterior visits are enough to appreciate their beauty.

The Leaning Tower is the star here. You can choose to simply snap photos pretending to hold up the tower or step inside for an up-close experience (additional fee applies). Reviewers often mention the “fun” of taking the classic photos but also the breathtaking views from the top if you decide to climb.

Return Journey

After a full day of exploring, the group heads back to Florence, arriving in the evening. The comfortable transportation and Wi-Fi make the return trip relaxing, giving you time to reflect on your Tuscan adventure.

What We Love About This Tour

Authentic regional experiences are woven throughout the day — from wine tastings to the guided tours of Siena’s grand cathedral and the free time in San Gimignano. The small group setting fosters a more intimate and engaging atmosphere, which many travelers find more enjoyable than larger tours.

The quality of the included lunch and wines receives consistent praise, with reviews noting that the meal is both hearty and expertly paired. The panoramic views from the estate and San Gimignano add to the visual appeal, allowing for memorable photos.

Most travelers appreciate the pace of the day — a good balance between guided activities and free time, offering a relaxed way to absorb Tuscany’s essence. The entrance tickets to Siena Cathedral are a thoughtful inclusion, avoiding long lines and hassle.

However, some mention that the itinerary can feel rushed, especially if you want to explore each place more deeply. The limited time in Pisa and San Gimignano might mean missing out on some hidden gems, but it’s a fair trade for seeing the highlights in one day.

Who Will Love This Tour?

This experience is ideal for first-time visitors to Tuscany who want a broad overview without the stress of local planning. It’s perfect for those who value cultural highlights, delicious food, and wine, all within a well-organized day trip. Travelers with limited time in Florence will find this a fantastic way to make the most of their stay.

But keep in mind, if you’re seeking deep dives into each city’s history or prefer to wander at leisure, you might find the schedule a bit too tight. The tour is best suited for active travelers eager to see the main sights with the convenience of transportation and guided commentary.

The Sum Up

This Siena, Pisa & San Gimignano tour offers a thoughtfully curated taste of Tuscany’s most cherished destinations. It combines guided sightseeing, free exploration, and delicious regional cuisine and wine into a single, well-balanced experience. The small group size enhances the personal touch, making it more engaging and comfortable than larger coach trips.

Whether you’re after breathtaking views, delicious Tuscan flavors, or historic landmarks, this tour delivers all that with a clear focus on value and authenticity. It’s particularly suitable for those who want an efficient, enjoyable way to experience Tuscany’s highlights without sacrificing comfort or local flavor.

If you’re seeking a full day of culture, scenic beauty, and regional gastronomy in Tuscany, this tour checks all the boxes — just be prepared for a busy but rewarding day.

FAQ

Is transportation included?
Yes, roundtrip transportation in a comfortable, air-conditioned minibus or minivan with Wi-Fi is included.

What is the meeting point?
The tour starts at the Tours & News KIOSK at Piazzale Montelungo, next to Santa Maria Novella Train Station in Florence.

How long is the tour?
The entire experience lasts approximately 11.5 hours, with specific start times available based on the day of booking.

Are meals included?
Yes, a Tuscan lunch at a family-run estate is part of the package, along with wine tastings.

Can I climb the Leaning Tower?
Climbing the tower is optional and not included in the standard tour. Additional tickets are required for interior access.

Is entrance to Siena Cathedral included?
Yes, entrance tickets to Siena Cathedral are included in the tour.

Is this tour suitable for children?
It’s generally suitable for most travelers, but note that the tour isn’t wheelchair accessible, and small children may find the long day tiring.

Are there any dress code requirements?
Yes, Siena Cathedral enforces a strict dress code — shoulders and knees must be covered.

What if I arrive late or miss the tour?
Late arrivals won’t be able to join the tour and won’t be eligible for refunds. Arrivals after the scheduled start time are not permitted.

Can I cancel or reschedule?
Yes, free cancellation is available up to 24 hours before the tour, and you can reserve now and pay later for flexibility.

This tour presents an excellent way to sample Tuscany’s highlights with comfort, flavor, and a touch of adventure. It’s perfect for travelers eager to combine sightseeing with regional tastings and a taste of medieval life.

You can check if your dates are available here: