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Every bookable experience in Italy, in one place — compared across GetYourGuide, Headout and Viator, ranked on reviews, booked on their site at their price.

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Discover the medieval towns of Siena and San Gimignano on a private day tour from Rome. Enjoy a wine tasting experience at a local winery in the Tuscan countryside, admiring stunning architecture and famous towers.

What's included

Fuel and Tolls
Water and Snacks
All taxes, fees and handling charges
Hotel pickup and drop-off
Well-maintained car with an English-speaking driver/Guide
Free Wi-Fi onboard
Licensed guides available to accompany you inside the attractions
Other beverages and meals
Tips and gratuities
Siena Duomo (Cathedral of Santa Maria Assunta)- approx. €8–€10
Italian Wine Tasting (Tuscany Wineries)- approx. €10–€25 per person

Before you go

Good to know

Throughout your ride, our drivers serve as informal local guides—sharing stories, history, and local tips at every stop. Please note that drivers are not permitted to enter museums or archaeological areas, but they’ll ensure you make the most of your visit with suggestions and background information before you explore on your own.
Some stops on your itinerary may be closed on the date of travel due to public holidays, maintenance or special events. We recommend verifying opening hours on the attraction’s official website or contacting us before your tour. If a stop is unexpectedly closed, we will try to offer a suitable alternative.
For 1-4 people: A comfortable sedan will be assigned to your group.
For 5-8 people: A spacious minivan will be assigned to your group.
Cancel up to 24 hours in advance for a full refund

What to bring

Comfortable shoes
Camera
Water

Restrictions & safety

Pets
Smoking in the vehicle
Wheelchair users

Destinations

Explore

Company

Legal

Rome to Tuscany Private Tour: Siena, San Gimignano & Wine Tasting

Overview

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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wines

Tuscany Day Trip from Rome: Lunch and Expert-Led Wine Tasting

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Rome to Tuscany Private Tour: Siena, San Gimignano & Wine Tasting

Overview

Rome Private Tour with English Speaking Driver: Explore the Eternal City

Rome: Award-Winning Trastevere Food Tour with Wine Pairings

Rome: Trastevere & Campo de' Fiori Street Food Walking Tour

Rome Graffiti Art Tour: Iconic Landmarks & Urban Vibe

Rome Private Highlights Golf Cart Tour with Gelato

Rome: Vespa Sidecar Tour of Hidden Gems & Iconic Sights with Gelato

Rome: Forbidden History Walking Tour & Pub Crawl with Drinks

Private Tour: Ancient Rome by Car - Colosseum, Catacombs & Appian Way

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wines

Tuscany Day Trip from Rome: Lunch and Expert-Led Wine Tasting

From Rome to Tuscany: Discover Florence and Pisa in One Day

Highlights

What's included

Before you go

Good to know

What to bring

Restrictions & safety

Destinations

Explore

Company

Legal

Rome to Tuscany Private Tour: Siena, San Gimignano & Wine Tasting

Overview

More to do nearby

Rome Private Tour with English Speaking Driver: Explore the Eternal City

Rome: Award-Winning Trastevere Food Tour with Wine Pairings

Rome: Trastevere & Campo de' Fiori Street Food Walking Tour

Rome Graffiti Art Tour: Iconic Landmarks & Urban Vibe

Rome Private Highlights Golf Cart Tour with Gelato

Rome: Vespa Sidecar Tour of Hidden Gems & Iconic Sights with Gelato

Rome: Forbidden History Walking Tour & Pub Crawl with Drinks

Private Tour: Ancient Rome by Car - Colosseum, Catacombs & Appian Way

Similar experiences to compare

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wines

Tuscany Day Trip from Rome: Lunch and Expert-Led Wine Tasting

From Rome to Tuscany: Discover Florence and Pisa in One Day

Rome to Tuscany Private Tour: Siena, San Gimignano & Wine Tasting

Overview

More to do nearby

Rome Private Tour with English Speaking Driver: Explore the Eternal City

Rome: Award-Winning Trastevere Food Tour with Wine Pairings

Rome: Trastevere & Campo de' Fiori Street Food Walking Tour

Rome Graffiti Art Tour: Iconic Landmarks & Urban Vibe

Rome Private Highlights Golf Cart Tour with Gelato

Rome: Vespa Sidecar Tour of Hidden Gems & Iconic Sights with Gelato

Rome: Forbidden History Walking Tour & Pub Crawl with Drinks

Private Tour: Ancient Rome by Car - Colosseum, Catacombs & Appian Way

Similar experiences to compare

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wines

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From Rome to Tuscany: Discover Florence and Pisa in One Day

Highlights

What's included

Before you go

Good to know

What to bring

Restrictions & safety