Explore Tuscany’s Quintessential Towns and Vineyards with a Full-Day Trip from Florence

This 11-hour guided tour offers an immersive experience through some of Tuscany’s most iconic spots, all from the comfort of a comfortable coach. For $91.73 per person, travelers get to visit San Gimignano, Monteriggioni, and Siena, with highlights like medieval towers, walled villages, and Renaissance architecture. The tour also features a guided wine tasting, a 3-course Tuscan lunch, and visits to renowned Chianti wineries. The group size is limited to 50 travelers, ensuring a relaxed atmosphere and attentive service.

While the itinerary can be flexible, it’s important to note that the order of stops may change, and November to March trips do not include Monteriggioni. The tour suits those eager for a comprehensive day of sightseeing, tasting, and cultural discovery, especially if they appreciate guided commentary and scenic drives through Tuscany’s rolling hills.

Key Points

Full-day guided tour from Florence covering San Gimignano, Monteriggioni, and Siena
Includes transport, a 3-course lunch, wine tasting, and optional cathedral visits
Scenic drive through the Chianti countryside with expert guides
Stops at well-preserved medieval towns with plenty of free time to explore independently
Small group size ensures a more personal experience
Not suitable for those looking for an in-depth, unhurried exploration of each site

If wine interests you, we've examined these other wine experiences in Florence

Tour Departure from Florence and Transport Details

The tour departs from Piazzale Montelungo, Florence at 8:00 am. It uses an air-conditioned coach to traverse the Tuscan hills, offering comfort during the day’s drive. The group size is capped at 50 travelers, which helps maintain an engaging atmosphere. The coach ride allows guests to relax and admire the landscapes, with the guide providing live commentary along the way.

San Gimignano: The Medieval Tower Town

The tour begins with a stop in San Gimignano, a UNESCO World Heritage Site famous for its tall medieval towers and frescoes. The town’s walls, dating back to the 13th century, are a highlight, offering scenic strolls with views over the Tuscan countryside.

Guests have around 2 hours of free time to wander through its narrow streets, explore historic buildings, and visit Piazza della Cisterna, a charming square surrounded by medieval towers and paved with traditional stones. The walls themselves are a popular photo spot, providing panoramic views of the town and landscape.

Monteriggioni: The Enclosed Medieval Village

A short drive from San Gimignano leads to Monteriggioni, a small fortified village encircled by well-preserved walls. This medieval gem remains largely unchanged, making it a perfect spot for pictures and strolling.

Guests enjoy free time to explore the interior, walk along the city walls, and soak in the authentic atmosphere of this ancient settlement. November to March, however, the stop at Monteriggioni is omitted, and the trip concludes approximately 30 minutes earlier.

Chianti Winery: Tasting and Lunch in a Hilltop Setting

From Monteriggioni, the tour continues through the gently rolling Chianti hills to a local winery. Here, visitors indulge in a guided tasting of three Chianti wines along with balsamic vinegar and extra virgin olive oil. The tasting session lasts about 1 hour and 30 minutes.

Following the tasting, a 3-course Chianti-style lunch is served, featuring local products with zero food miles, including cantucci and Vin Santo to finish. The lunch is designed to highlight Tuscan flavors and wine pairings, making it a highlight for culinary enthusiasts.

Keen to taste more of Florence? We've looked into these other food and drink experiences

Siena: The Renaissance City

The final major stop is Siena, renowned for its medieval architecture and Renaissance art. The guided walking tour covers the historic city center, including Piazza del Campo, home to the Palio di Siena horse race, and the Palazzo Pubblico.

Guests also visit Piazza Salimbeni, where the Palazzo Salimbeni houses the world’s oldest bank. If the optional cathedral interior visit is selected, visitors can admire the striped marble façade, polychrome floors, and frescoes inside the Siena Cathedral.

The guided tour lasts approximately 2 hours and 30 minutes, after which there is free time to explore or relax before returning to Florence.

Siena Cathedral and Optional Piccolomini Library Visit

The interior of Siena Cathedral is an architectural marvel, featuring vibrant polychrome marbles and spectacular artwork. Visitors can choose to include an inside visit if the optional ticket is purchased.

Those opting for the Piccolomini Library tour will see frescoes by Pinturicchio, depicting scenes from the life of Pope Pius III, providing a cultural highlight within the cathedral. The library visit lasts about 10 minutes and is an extra.

Scenic Return Through Chianti’s Vineyards and Villages

On the way back to Florence, the group travels through the Chianti road, known as Strada Statale 222 Chiantigiana. The route offers spectacular views of vineyards, olive groves, and medieval castles. This scenic drive allows guests to enjoy the authentic Tuscan landscape before arriving back in Florence in the evening.

Practical Details, Tips, and Limitations

The tour includes transportation, a guided commentary, and small group size, contributing to a comfortable and engaging experience. The tour begins at 8:00 am and typically concludes in Florence in the evening, with return times depending on the season and itinerary adjustments.

Guests should wear comfortable shoes due to uphill walking at several stops and bring ID for visits requiring ticket verification. The tour follows a flexible schedule, and November to March trips omit Monteriggioni and are about 30 minutes shorter.

Some reviews highlight the value for money, especially given the full day of visits, tastings, and meals, though a few mention crowds at Siena’s cathedral or longer walking times. The guides are praised for their knowledge, with Sandro, Fabiana, and Riccardo receiving particular mention.

San Gimignano, Siena, Monteriggioni, Chianti: A Well-Rounded Tuscan Day Trip

This guided tour offers a balanced blend of history, scenery, and culinary delights. It’s especially suited for those seeking efficient access to multiple towns without the hassle of driving. The wine tasting and lunch provide a taste of authentic Tuscan flavors, while the scenic drives through Chianti’s hills make for memorable views.

While the itinerary is busy and involves significant walking, the small group size and expert guides help mitigate fatigue and enhance the experience. The flexibility in stops and optional visits mean travelers can tailor the day to their interests, making this tour a convenient and enjoyable way to see Tuscany’s highlights.

✨ Book This Experience

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

4.5

“Our tour guides Assia, Alexandra and Enrico were fabulous. They were knowledgeable, respectful, and resourceful. They added so much underst…”

— Janet D, Featured

Frequently Asked Questions

What is included in this tour?
The tour includes transport by air-conditioned coach, live commentary, a 3-course Tuscan lunch, and wine and balsamic vinegar tastings. Optional visits to Siena Cathedral and the Piccolomini Library may be included if selected.

How long does the tour last?
The entire trip lasts approximately 11 hours, starting at 8:00 am and returning to Florence in the evening.

Is the tour suitable for all fitness levels?
Yes, but comfortable walking shoes are recommended due to uphill walks and cobblestone streets. The tour involves a fair amount of walking.

What happens if I want to skip some stops?
It’s possible to skip optional visits like the cathedral if desired. The tour is flexible, but the schedule may be adjusted accordingly.

Does the tour operate year-round?
Yes, but from November to March, the stop at Monteriggioni is omitted, and the tour duration is about 30 minutes shorter.

Are children allowed on this tour?
The tour is generally suitable for older children who can walk comfortably and enjoy sightseeing. No specific age restrictions are mentioned.

What should I bring?
Bring ID, comfortable shoes, and weather-appropriate clothing. It’s also wise to carry some cash or cards for personal purchases.

Can I take photos inside the Siena Cathedral?
If the interior visit is included, photography may be restricted inside the cathedral. Check local rules on-site.

Is this tour wheelchair accessible?
The data does not specify accessibility, so travelers with mobility concerns should inquire directly.

How can I book this tour?
You can book through the official site or Viator, with most bookings made 53 days in advance. The tour has a full cancellation policy up to 24 hours before.

What is the overall value of this tour?
Considering the all-inclusive price, multiple stops, guided commentary, and local tasting experiences, this tour offers good value for a full-day exploration of Tuscany’s most famous sites.