Tuscany Day Trip: Siena, San Gimignano & Pisa with Lunch & Wine

Three Medieval Towns & a Winery in One Day from Florence

You leave Florence early by coach, spend a guided hour in Siena learning about the city's medieval squares and cathedral, then drive through the countryside to a family-owned winery for a three-course Tuscan lunch with wine pairing. After that, you have free time to explore the medieval towers of San Gimignano and the white marble monuments of Pisa, including the Leaning Tower. The coach returns you to Florence the same evening, with all transport, the Siena guide, and lunch included.

Step-by-step itinerary

• Meet guide at Piazzale Montelungo
• Travel to Siena by coach
• Guided walking tour of Siena
• Visit Piazza del Campo
• See Torre del Mangia clocktower
• Explore Siena Cathedral exterior
• Drive to winery near San Gimignano
• Enjoy three-course lunch with wine pairing
• Drive to San Gimignano
• Visit panoramic viewpoint
• Free time in San Gimignano
• Explore Piazza della Cisterna and Cathedral
• Drive to Pisa
• Visit Square of Miracles
• Free time to explore Pisa and Leaning Tower
• Return to Florence by coach

The Experience

You're standing in Florence, and the Leaning Tower is an hour away by coach. Most visitors stay put, thinking Tuscany means the city. But the real Tuscany—the one with vineyards rolling into the horizon, medieval towers still standing after seven centuries, and a lunch that tastes like it came from someone's grandmother's kitchen—sits outside the walls. This day trip pulls you out of the crowds and into three towns most tourists skip: Siena first, where a professional guide walks you through Piazza del Campo (the square where they still race horses bareback every summer) and past the Siena Cathedral; then San Gimignano, a hilltop village with thirteen intact medieval towers that locals call a medieval Manhattan; and finally Pisa, where you get an hour to photograph the Leaning Tower, climb it if the queue allows, and wander the white marble Piazza dei Miracoli on your own time.

The day starts early at Piazzale Montelungo Bus Terminal, a five-to-ten-minute walk from Santa Maria Novella train station. You board a coach with air conditioning and Wi-Fi, and for the next hour your guide talks you through what you're about to see—the history, the palio horse race, why these towns matter. When you reach Siena, a local guide takes over for about an hour, moving you through the city's main squares and landmarks: the Palazzo Pubblico, the Torre del Mangia (the third tallest tower in all of Italy), and the cathedral with its Renaissance frescoes. Then you have free time to walk the narrow streets, grab a coffee, sit in the piazza. After that, the coach drives you another hour through the Tuscan countryside to a family-owned winery outside San Gimignano. You sit down to a three-course lunch—a meat and cheese plate, pasta, dessert—paired with wines from the estate, all of it surrounded by olive groves and rolling hills. It's the kind of meal that makes you understand why people move to Tuscany.

San Gimignano comes next, and you get an hour to walk it. The town is small enough that you can't get lost, and the main square (Piazza della Cisterna) is where everyone ends up anyway—it's where the cathedral is, where you can buy gelato, where the views back out over the countryside are the ones you'll remember. Then it's another hour to Pisa, where the Leaning Tower sits in the middle of a perfect green lawn surrounded by white marble buildings. You have about an hour there too, which is enough to walk around the Piazza dei Miracoli, go inside the cathedral if you want, and either climb the tower or just take the famous photo where you're pretending to hold it up. The coach brings you back to Florence around evening, and you've seen more of Tuscany than most people who stay for a week.

What’s included

Your day includes hotel or meeting-point pickup (Piazzale Montelungo Bus Terminal in Florence), round-trip coach transport with air conditioning and Wi-Fi, a professional multilingual Tour Leader throughout, a guided walking tour of Siena with a local guide and headsets, a three-course Tuscan lunch with wine pairing at a family-owned winery in the countryside, and free time to explore San Gimignano and Pisa on your own. Entry fees to monuments in Pisa and San Gimignano are not included, nor is climbing the Leaning Tower.

Good to know

Moderate physical levelStroller friendlyInfant seats availablePublic transport nearbyNot for heart conditionsNot for back problemsInfants must sit on laps

Operated by Ciao Florence Tours Srl

Is this one for you?Pick this if you want to see three of Tuscany's most famous medieval towns in a single day without arranging your own transport, hiring separate guides, or figuring out timing—the fixed schedule and included lunch mean you show up and the day unfolds around you.

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Top questions

What time does the tour start and where do I meet the group?

Meet at Piazzale Montelungo Bus Terminal early in the morning. It's a 5–10 minute walk from Santa Maria Novella train station in Florence. The exact departure time will be confirmed when you book.

Is lunch included, and what if I'm vegetarian or have dietary restrictions?

Yes, a three-course Tuscan lunch with wine pairing at a countryside winery is included (unless you select the Low Cost option). The operator can accommodate vegetarian and gluten-free meals with prior notice.

How much free time do I get in each town?

Siena includes a guided walking tour (about an hour) plus free time afterward. San Gimignano and Pisa each offer about an hour of free time to explore on your own.

Can I climb the Leaning Tower of Pisa?

Yes, you can climb it during your free time in Pisa if there's no queue. Climbing is not included in the tour price, so you'd pay separately at the site.

What languages is the guide available in?

English and Spanish are always available. French, Italian, and Portuguese are offered on specific days with a minimum group size (check the booking page for your travel date). Chinese, Korean, and Japanese use an audio guide app with a Tour Leader managing logistics.

How long is the full day, and what time do I return to Florence?

It's a full day trip. You depart early in the morning and return to Piazzale Montelungo in Florence around evening (approximately 10–12 hours total, depending on traffic).

Is the coach comfortable for a long day?

Yes, the coach is fully fitted with air conditioning and free Wi-Fi on board, so you can rest between stops.

What if I don't want the guided tour in Siena or the lunch?

The operator offers a Semi-Independent option (no Siena guide) and a Low Cost option (no lunch or Siena guide). You can choose these when booking.

Is this tour suitable for families with young children?

Yes. Infants can ride in a pram or stroller, and specialized infant seats are available. However, the tour involves several hours on a coach and walking through medieval towns, so consider your child's comfort with that pace.

Can the order of the towns change?

Yes, the itinerary order may change depending on the day and logistics. You'll always visit all three towns and the winery, but the sequence might differ from what's described.