Day Trips

From Florence: Pisa, Siena, San Gimignano & Chianti Day Trip with Wine Tasting & Lunch

Name: From Florence: Pisa, Siena, San Gimignano & Chianti Day Trip with Wine Tasting & Lunch
Start: 2026-10-07T07:30:00
End: 2026-10-07T19:30:00
Location: Florence

A Tuscany day trip that actually earns its length; four stops, a winery lunch, and three wine tastings, all without renting a car or planning a thing.

4.3/5(1,960)

Calagiu M

Group

Verified booking

2 weeks ago

The guide, the information we received, superb San Gimignano, the lunch and wine tasting were very beautifully organized, and Pisa and Siena were outstanding. The whole trip was well worth the money.

Lisa Z

Couple

Verified booking

Last week

Great tour. Got to see a lot of places we wouldn't have been able to go to. Tour guide Roberto and Maya and driver Luca were wonderful!! Highly recommend

Graham W

Solo

Verified booking

Last week

Fine tour but exhausting maybe too much travel? Good lunch experience in Chianti Tour guide was excellent though out the trip unfortunately couldn't give a gratuity because had no cash who does anymore?

Thida L

Couple

Verified booking

Aug 2026

The guide Cloudia was great, very helpful. The bus was comfortable and cool A/C. The destination and wine tasting was satifiying. We had a good time. Worth the price.

Arian D

Group

Verified booking

Aug 2026

This was a really great tour of these towns. Lunch, views and the timing were all very nice. Plus all that the tour leader, Claudia was really great.

Marita B

Solo

Verified booking

Jun 2026

A wonderful experience. Laura was our guide and Michel was our driver. Michel is a great driver, and we felt very comfortable with his driving. Laura gave us some great suggestions on what to do and where to go. We visited Pisa, Siena, the Chianti vineyards, and San Gimignano. An experience we’ll never forget.😍❤️

Explore four of Tuscany’s most iconic destinations in one well-planned day trip from Florence.

Enjoy free time in Pisa, San Gimignano, and Siena to explore at your own pace.

Savor authentic Tuscan flavors with a winery visit, wine tastings, and a traditional local meal.

Upgrade your experience with guided tours of Siena and its cathedral or access to Pisa’s famous tower.

Travel comfortably with round-trip AC coach transfers and a multilingual tour leader throughout.

Round-trip AC coach transfers from Florence

Onboard Wi-Fi access

Multilingual tour leader

Free time in Pisa, Siena & San Gimignano

Chianti winery visit with 3 wine tastings

Traditional Tuscan lunch

Siena guided tour (as per option selected)

Siena Cathedral guided tour (as per option selected)

Leaning Tower of Pisa access (as per option selected)

Hotel transfers

Personal expenses

TOTAL DURATION12 hours
MODE OF TRANSFERA/C Bus
Start point
Central Florence
Get direction
1 hr 30 min by a/c bus
1. Siena
2 hr
2 attractions
You can choose to either freely explore Siena, or avail a guided tour of the city center and maybe even its cathedral.
Highlights
Piazza del Campo
Siena Cathedral
45 min by a/c bus
2. Chianti Vineyard
1 hr 30 min
30 min by a/c bus
3. San Gimignano
1 hr 15 min
1 attraction
1 hr 30 min by a/c bus
4. Pisa
1 hr 15 min
1 attraction
1 hr 30 min by a/c bus
End point
Central Florence
Get direction
Your ending point would be same as your start point

You can cancel these tickets up to 48 hours before the experience begins and get a full refund.

1,960 reviews
How do we collect reviews?
These ratings include verified reviews from both Headout guests and our trusted partners who operate this experience locally. All reviews come from real travelers who've taken this experience.
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Guests from Canada, United States, India and over 23 countries have loved this experience
What our guests say
Graham W
Solo
Verified booking
Last week
Fine tour but exhausting maybe too much travel? Good lunch experience in Chianti Tour guide was excellent though out the trip unfortunately couldn't give a gratuity because had no cash who does anymore?
Calagiu M
Group
Verified booking
2 weeks ago
The guide, the information we received, superb San Gimignano, the lunch and wine tasting were very beautifully organized, and Pisa and Siena were outstanding. The whole trip was well worth the money.
Lisa Z
Couple
Verified booking
Last week
Great tour. Got to see a lot of places we wouldn't have been able to go to. Tour guide Roberto and Maya and driver Luca were wonderful!! Highly recommend
Madina C
Couple
Verified booking
3 weeks ago
It is a well organized tour, we loved everything and our tour guide Chiarra was great!
Cristina C
Couple
Verified booking
Last week
It was a chance to see other parts of Tuscany.

Start your day with a comfortable departure from Florence aboard an AC coach equipped with Wi-Fi, setting the tone for a relaxed journey through Tuscany.

Pisa

Arrive at Piazza dei Miracoli, home to some of Italy’s most striking architecture. Take time to admire the Cathedral, Baptistery, and Monumental Cemetery, and snap photos of the iconic Leaning Tower. If you’ve chosen the upgrade, climb to the top for sweeping city views.

Chianti

Leave the city behind and head into the rolling hills of Chianti. Visit a local winery where you’ll enjoy a traditional Tuscan lunch paired with three regional wine tastings, surrounded by vineyard landscapes.

San Gimignano

Continue to this medieval hill town known for its skyline of stone towers. Stroll through its narrow streets, explore artisan boutiques, and take a break at a local café or gelateria in the main square.

Siena

End your day in Siena, a city rich in history and tradition. Visit Piazza del Campo, the heart of the city and home to the famous Palio horse race. With upgraded options, join a guided walking tour and explore the Siena Cathedral’s intricate interiors. Enjoy free time to relax or explore before heading back.

Return to Florence in the evening after a full day of exploration, culture, and Tuscan flavors.

What to bring

Wear comfortable walking shoes because the tour involves a fair amount of walking.

If you plan to visit Siena Cathedral, wear clothing that covers your knees and shoulders.

Bring a valid ID if you intend to participate in the wine tasting sessions.

Accessibility

The tour is not suitable for wheelchair users or guests with prams or strollers.

What’s not allowed

Guests under 18 years old will not be served alcoholic beverages during the wine tastings.

Additional information

Guests under 18 years old may join the tour only when accompanied by at least one adult.

The sequence of visits to Pisa, San Gimignano, Siena, and Chianti may change due to traffic or local conditions.

Hotel transfers are not included in this experience; you must reach the meeting point in central Florence on your own.