Private Day Trip: Rome to Siena & San Gimignano with Wine Tasting

DEAL

Private Day Trip: Rome to Siena & San Gimignano with Wine Tasting

12 hour(s)

English (United Kingdom)

Rome, Italy

Free cancellation

Up to 24 hours

Instant confirmation

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Modify your booking anytime

No extra fees

Best price guarantee

No hidden fees

Travel from Rome in comfort with a dedicated private driver

Explore the enchanting town of Siena with your own private guide

Discover the captivating medieval town of San Gimignano

Admire the splendid landscapes of the rolling Tuscan hills

Savor a tasting of the region's renowned Chianti wine

Enjoy panoramic views of vineyards and olive groves

Leave the vibrant pace of Rome behind as you embark on a captivating day trip into the heart of Tuscany. Your personal driver will greet you at your hotel, ready to transport you north into a world of breathtaking landscapes. As you travel from Rome to Siena, watch the scenery transform into the classic Tuscan countryside. You will be fascinated by the endless rolling hills, where neat rows of vineyards and silvery olive groves stretch towards the horizon. Glimpse tall cypress trees lining winding roads and fields of golden sunflowers basking in the Italian sun, a truly picturesque introduction to the region.

Upon arriving in the magnificent city of Siena, your private guide awaits to lead you through its historic streets, including a visit to the iconic Piazza del Campo, one of Italy’s most beautiful medieval squares, and share its rich stories. After immersing yourself in Siena's unique charm, the journey continues to the iconic hilltop town of San Gimignano. Famous for its striking medieval towers that create an unforgettable skyline, this town is a journey back in time.

REDUCED–Summer Madness

Price start from

$ 1642.64

$ 1560.51

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Participants

Adult (6 - 100)

Infant (0 - 5)

July 2026

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Enjoy unlimited changes and full refund options.

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Free cancellation and unlimited rescheduling leads to total flexibility while you plan your travels

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What's Included

Private transport
Wine tasting
San Gimignano free time
Siena guided tour
Hotel drop-off

What's Not Included

Gratuities

Comfortable walking shoes

Sun hat and sunglasses

Valid ID or Passport

Camera or smartphone

Light jacket

Pregnant travelers
Travelers with heart conditions
Travelers with Limited mobility impairments
Travelers with serious medical condition
Travelers with back problems
Guests Prone to Motion Sickness
Children under 18 years

Wine lovers
Couples and honeymooners
Food lovers

Strollers and infant seats are available; not for wheelchairs or pets

Provide contact info and check email for your 7:30 AM pickup confirmation

Pickup is from locations within 10 kilometers of the Pantheon in Rome

Cover knees and shoulders for church entry; infants require their own seat

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Customer Reviews

Explore More A Tuscan Dream: Day Trip to Siena & San Gimignano with Wine Tasting

Day In a City

Explore More A Tuscan Dream: Day Trip to Siena & San Gimignano with Wine Tasting

Escape the hustle of Rome for a day and immerse yourself in the rolling hills of Tuscany. Our unforgettable day trip whisks you away to two of Italy's most enchanting medieval towns. First, explore Siena, a city frozen in time. Wander its cobblestone streets to the magnificent Piazza del Campo, the shell-shaped heart of the city, famous for its historic Palio horse race. Next, we journey to the stunning hilltop town of San Gimignano. Known as the "Medieval Manhattan," its skyline of ancient towers offers breathtaking panoramic views of the Tuscan countryside. The highlight of our adventure is a visit to a traditional winery nestled in the Chianti region. Here, you'll indulge in a guided tasting of world-renowned wines, perfectly paired with local cheeses and delicacies. It’s a true taste of la dolce vita. This isn't just a tour; it's an experience that will captivate your senses. Ready for your Tuscan adventure? Book your Siena and San Gimignano day trip from Rome today and create memories that will last a lifetime!