Private Tuscany Day Trip from Florence: Siena, San Gimignano & Chianti
About this activity
Highlights
- Discover Tuscany’s medieval treasures in one seamless day – Explore Siena’s Gothic cathedral, San Gimignano’s towers & Chianti’s rolling vineyards.
- Experience Siena’s rich history & traditions – Visit the UNESCO-listed Piazza del Campo, home to the legendary Palio horse race, and more with a local guide.
- Tour a historic family-run vineyard – Visit a renowned Tuscan winery, sample local varietals, and learn the secrets of world-famous Chianti.
- Savor a farm-to-table Tuscan lunch – Enjoy a homemade, locally sourced meal, paired with the winery’s finest Chianti wines.
- Travel in comfort with a private driver – Sit back, relax & enjoy a stress-free Tuscany experience.
Full description
Discover Three Stunning Destinations on a Perfectly Planned Tuscany Day Trip
Rolling hills, medieval towns, and world-class wines—this is the Tuscany of your dreams. On this Private Tuscany Day Trip from Florence, travel in comfort with a dedicated English-speaking driver, exploring Siena, San Gimignano, and the Chianti wine region on an all-inclusive Tuscan adventure.
With a farm-to-table lunch at a family-run vineyard, a walking tour of Siena with a local guide, and a seamless itinerary designed for maximum relaxation and discovery, this private tour is the best way to experience Tuscany in a single day.
Explore Siena’s History, Art & Medieval Traditions
Your day begins with Siena, one of Tuscany’s most breathtaking medieval cities. Once you arrive, you'll meet your private guide and discover:
• Piazza del Campo – The heart of Siena, home to the Palio horse race and the stunning Mangia Tower.
• Siena Cathedral (Optional Visit) – Admire the intricate black-and-white marble façade and breathtaking interiors.
• Local Traditions & Historic Streets – Stroll through centuries-old alleyways and discover the unique culture of Siena’s Contrade (neighborhoods).
Enjoy a Farmhouse Lunch & Wine Tasting in Chianti
No Tuscany tour is complete without exceptional food & wine. After saying goodbye to your local guide in Siena, you’ll hop back in the car and head to a family-run Chianti vineyard, where you’ll enjoy:
• A guided tour of the winery & vineyard – Learn the secrets behind Chianti Classico & Super Tuscan wines.
• A homemade, farm-to-table lunch – Savor a seasonally inspired Tuscan meal made with fresh local ingredients, paired with the vineyard’s finest wines.
• Tuscan Hospitality at Its Finest – Experience the warmth of true Italian countryside living with local winemakers. Step Into a Fairytale in San Gimignano
With full bellies, you’ll continue to San Gimignano, one of Tuscany’s most famous hilltop villages. Here, you’ll have free time to explore on your own. These are some ideas of how to spend the perfect afternoon:
• Wander its medieval streets – Admire the town’s 14 historic towers and breathtaking panoramic views.
• Shop local artisan goods – Browse handmade ceramics, olive oils, and wines unique to this region.
• Taste Italy’s best gelato – Visit Gelateria Dondoli, a world-famous gelateria known for its award-winning flavors.
Why Choose a Private Tuscany Tour?
This private tour follows a carefully planned route, ensuring you experience Tuscany’s most beautiful towns and best wine regions in one effortless day. With a dedicated guide in Siena, private driver, and all logistics handled for you, it’s the most relaxing, personal, and immersive way to see Tuscany from Florence.
Included / Excluded
- Expert English-speaking guide
- Designated professional driver
- Air-conditioned transport
- Expertly guided walking tour of Siena
- Gourmet lunch and wine tasting in Chianti
- Free time in San Gimignano
- Hotel Pick-Up/Drop-Off
- Gratuities
- Entrance tickets to the Siena Cathedral
Meeting point
Start Location
Piazza della Repubblica, Piazza della Repubblica, 50123 Firenze FI, Italy
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.
Get directions →Important information
Know before you book
- 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.
- Walks and Devour comply with all local government regulations. Please refer to local government guidelines for the most up to date information.
Know before you go
- Please arrive 15 minutes before your tour start time for check-in. Out of courtesy to other guests, we’re unable to wait for latecomers. No refunds can be provided for late arrivals or no-shows.
- Those with dietary restrictions or food allergies need to email our Guest Experience team at info@takewalks.com after booking the tour so we can arrange your lunch.
- If you are traveling with a small child, please contact us. We need to confirm space on the vehicle for them.
- Luggage and/or strollers are not allowed on this tour as there is no extra storage space on the vehicle.
- 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. Please note that due to the religious nature of Siena cathedral, all individuals regardless of gender must cover their shoulders and knees. A scarf or shawl is acceptable. Walks cannot be held responsible for those denied entry.
- Tips/gratuities (for your guide) are always appreciated.
- Walks and Devour comply with all local government regulations. Please refer to local government guidelines for the most up to date information.
Cancellation policy
Cancellations received greater than 7 days prior to tour commencement are fully refundable. Cancellations received within 7 days of tour commencement are nonrefundable. Amendment requests are subject to availability and price changes. Late arrivals and no shows are nonrefundable. This is applicable to any tour participant that fails to arrive, or arrives after tour departure.
Additional information
- Adult (15+)
- Child (2-14)
- Infant (0-1)