Tuscany Florence Day Trip to Chianti
Discover Tuscany's Charm on a Day Trip from Florence with Wine Tasting and Gourmet Lunch

Toscana
people
1 participant
hours
- • Explore Chianti and Medieval Siena on a Florence Day Trip
- • Enjoy a Full-Day 9-Hour Tour with Wine Tasting and Lunch
- • Experience Tuscany's Only Small-Group Wine and Food Adventure
Why We Love This Unique Experience
Experience the enchanting beauty and rich flavors of Tuscany on an unforgettable day trip from Florence to the breathtaking regions of Chianti, Siena, and San Gimignano. This journey promises to immerse you in the charm of medieval towns, picturesque vineyards, and delectable cuisine. Whether it's the stunning landscapes or the aromatic wines, each moment spent on this tour will leave lasting memories of Italy's heartland.
The adventure begins with a comfortable ride through the rolling hills of Tuscany, where scenic views unfold at every turn. The first stop is the historic city of Siena, renowned for its remarkable architecture and vibrant culture. With a knowledgeable guide, explore the narrow, cobblestone streets, and visit iconic landmarks like the magnificent Cathedral of Siena. Next, indulge in a delightful Chianti wine tasting at a family-owned estate, where local wines are perfectly paired with an authentic Tuscan lunch made from fresh regional ingredients. Afterward, head to the charming town of San Gimignano, famous for its medieval towers and UNESCO World Heritage status, where time seems to stand still amidst its ancient beauty.
This day trip is not just an extraordinary adventure; it also makes for a fantastic gift for friends and loved ones who cherish travel, culture, and cuisine. Offering unique experiences like wine tasting, gourmet meals, and exploration of historic towns, this tour is the perfect way to share the magic of Tuscany. Give the gift of unforgettable memories and a taste of Italy's finest adventures!
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Experience Overview:
Florence Day Trip: Chianti Wine Tasting, Siena, San GimignanoExperience the best of Tuscany on this Florence day trip to Chianti, Siena, and San Gimignano. Enjoy a Chianti wine tasting at a local estate, explore the medieval streets of Siena and San Gimignano, and savor a delicious Tuscan lunch with regional specialties included in your tour. Led by a local expert guide, this small-group tour combines culture, history, and food for the ultimate Tuscan adventure.
Meeting Point
Piazza della Repubblica
Piazza della Repubblica, 50123 Firenze FI, Italy
Please arrive 15 minutes prior to the start of your tour, your guide will be holding a green Walks sign. This tour meets by the Carousel in Piazza della Repubblica.
What's included:
- Expertly guided walking tour of Siena
- Expertly guided walking tour of San Gimignano
- Expert English-speaking guide
- Designated professional driver
- Gourmet lunch and wine tasting in Chianti
- Air-conditioned transport
Not included:
- Gratuities
- Hotel Pick-Up/Drop-Off
What to expect:
Duration: 9 hours
Tuscany
Your driver and guide will pick you up in a comfortable, air-conditioned transport in central Florence and drive you through the hills of Tuscany. You'll pass the best panoramic viewpoint of Florence and pause for pictures.
1 hour, 30 minutes
Siena
Siena
Siena is one of the best-preserved examples of medieval Italian architecture in the world. Spared German bombing in WWII, this time capsule of ancient, precarious-looking buildings is home to the Palio, one of the greatest and most dangerous horse races in the world.
1 hour, 30 minutes
Duomo di Siena
Piazza del Duomo 8, , Siena, 53100
Your expert tour leader will immerse you in the unique history and culture of Siena as you explore its narrow streets including an exterior visit to the Siena Cathedral - a Tuscan gem!
15 minutes • Admission Ticket Not Included
Piazza del Campo
Il Campo, , Siena, 53100
Pause amidst the square where fervent horses race to win the honor of bringing home the palio - a handpainted silk banner of the highest regard.
15 minutes
Tuscany
Stop At: Chianti
Walking the hills of Tuscan towns will make you hungry so your next stop is an authentic Italian family farm where some of our good friends will give you a behind-the-scenes tour of the vineyards, winery, and wine cellars before sitting you down for a sumptuous, all-inclusive lunch of local, seasonal ingredients. Your meal will be paired with Chianti wines specially selected to perfectly complement the flavors of each dish.
3 hours
San Gimignano
San Gimignano
After indulging your taste buds, indulge your imagination with a final stop at San Gimignano, a town of such unique architectural beauty it has been designated a UNESCO World Heritage Site.
1 hour, 30 minutes
Piazza della Repubblica
Piazza Della Repubblica, , Florence, 50123
At the end of the day, hop aboard your comfortable private coach bus back to Florence. We've taken care of the logistics so all you have to do is enjoy the food, the sights, and the scenery.
1 hour
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Details & Important Info
Additional Experience Details & Important Information
Public transportation options are available nearby
Specialized infant seats are available
Suitable for all physical fitness levels
This tour is in English.
Unfortunately due to the nature of this tour it is not suitable for guests with mobility impairments or with wheelchairs, or strollers.
This is a walking tour. Guests should be able to walk at a moderate pace without difficulty.
Those with dietary restrictions need to contact us after booking the tour so we can arrange your lunch. Unfortunately, we cannot accommodate vegans or those with celiacs.
Tickets for the Siena Cathedral are not included in the tour price. If you wish to visit the Cathedral, your guide will assist you. The Cathedral is closed on Sundays and for certain holy days.
In order to get into the city center, we utilize small luxury minivans. This allows us to avoid the parking lots outside of the center requiring us to walk. Your guide may need to split time between vehicles on groups larger than 8.
Walks and Devour comply with all local government regulations. Please refer to local government guidelines for the most up to date information.
Cancellations & Refunds
Reservation Changes, Cancellations & Refunds
Changes to reservations for tickets can be made until 3 days prior to the date scheduled. Reservations may be re-scheduled by the operator of the activity due to reasons such as weather, minimum participation requirements, mechanical issues or other interruptions beyond their control.
Organized by
Walks - Italy, Spain & Greece
Product SKU: IT-58487-0024
Tuscany Day Trip to Chianti and Siena
Toscana
people
1 participant
hours
- • Explore Chianti and Medieval Siena on a Florence Day Trip
- • Enjoy a Full-Day 9-Hour Tour with Wine Tasting and Lunch
- • Experience Tuscany's Only Small-Group Wine and Food Adventure
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