Tuscany’s enchanting allure draws visitors from around the world. On this full-day tour from Rome, guests will enjoy the region’s medieval charm, exploring three picturesque towns – Monteriggioni, San Gimignano, and Castellina in Chianti. From the iconic skyline of San Gimignano to the boutique winery where they’ll savor local vintages, this journey promises an authentic taste of Tuscany’s timeless beauty and rich cultural heritage. What delights await as travelers discover the essence of this captivating Italian landscape?

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Key Points

This full-day private tour from Rome takes visitors to the Tuscan towns of Monteriggioni, San Gimignano, and Castellina in Chianti.
The tour includes free time to explore the medieval walled town of Monteriggioni and the UNESCO-listed San Gimignano.
Visitors will enjoy a guided tour and wine tasting at a boutique winery in Chianti, accompanied by a light lunch.
Transportation is provided in an air-conditioned, fully insured vehicle with an English-speaking driver.
The tour offers captivating views of the Tuscan countryside throughout the journey.

Tour Overview

This full-day trip from Rome to the Tuscan towns of Monteriggioni, San Gimignano, and Castellina in Chianti offers hassle-free logistics with private transportation.

Guests can explore the region’s culture and cuisine without coordinating public transit. The itinerary includes free time to wander Monteriggioni and San Gimignano, as well as a visit to a boutique winery for a tour, tasting, and light lunch.

An air-conditioned, insured vehicle with an English-speaking driver provides scenic countryside views throughout the day. The tour is available with or without a dedicated local guide, and infants can be accommodated upon request.

Looking for more options in Rome? We've reviewed plenty of other experiences.

Itinerary Highlights

Guests begin the day with free time to explore the medieval walled town of Monteriggioni, marveling at its well-preserved towers and charming atmosphere.

Next, they travel to the UNESCO-listed town of San Gimignano, where they can discover its iconic skyline of medieval towers and stroll through the historic center.

The tour then visits a boutique winery in the Chianti region, offering a guided tour, wine tasting, and a light lunch featuring local cuisine and flavors.

Throughout the day, guests enjoy scenic views of the rolling Tuscan countryside, capturing the essence of this iconic region.

Inclusions

The full-day tour from Rome includes hotel pickup and drop-off, ensuring a hassle-free experience.

Guests will travel in an air-conditioned, fully insured vehicle with a professional English-speaking driver. If selected, a dedicated licensed local expert tour guide will provide insights throughout the journey.

The tour includes a light lunch and wine tasting at a boutique winery, allowing participants to savor the flavors of Tuscan cuisine and vintages.

Participants can savor the flavors of Tuscan cuisine and vintages with a light lunch and wine tasting at a boutique winery.

For families, an infant seat is available upon request.

With these comprehensive inclusions, travelers can focus on seeing the Tuscan culture and countryside.

Booking Information

Prices for the full-day tour from Rome start at $761.59 per person, varying based on group size.

Travelers can reserve the tour now and pay later. The tour offers free cancellation up to 24 hours before the experience.

This private tour is for your group only – it won’t be shared with others. The tour departs at 7:30 AM and the driver may make 2-3 stops for additional passenger pickups if you select the shared tour option.

The tour isn’t wheelchair accessible, but most travelers can participate.

Reviews highlight the tour’s flexibility and the enjoyment of the private experience.

Additional Details

This private tour isn’t wheelchair accessible, though most travelers can participate.

The departure time is 07:30 AM, allowing ample time to explore the Tuscan countryside.

Departing at 07:30 AM, ample time to explore the Tuscan countryside.

In the shared tour option, the driver may make 2-3 stops for passenger pickups.

All transportation is provided in an air-conditioned, fully insured vehicle with a professional English-speaking driver.

Travelers can enjoy a light lunch and wine tasting at a boutique winery, with a minimum drinking age of 18.

Free cancellation is available up to 24 hours before the experience, and a reserve now, pay later option is offered.

There's plenty more to explore in Rome

A Picturesque Journey Through Tuscany

As travelers embark on this full-day excursion from Rome, they’ll be captivated by the picturesque landscapes of Tuscany.

First, they’ll explore the medieval town of Monteriggioni, marveling at its well-preserved walls and charming atmosphere.

Then, they’ll visit the iconic towers of San Gimignano, a UNESCO World Heritage site.

The tour culminates with a stop at a boutique winery in Castellina in Chianti, where they’ll indulge in a wine tasting and light lunch, seeing the region’s renowned culinary and viticultural traditions.

Throughout the journey, travelers will be treated to stunning vistas of rolling hills, vineyards, and olive groves.

Explore the Charming Towns of Monteriggioni and San Gimignano

Nestled within the rolling Tuscan landscape, the medieval walled town of Monteriggioni captivates visitors with its well-preserved defensive structures and charming ambiance.

Visitors can stroll along the town’s encircling walls, admiring the 14 towers that once protected its residents.

Meandering the town’s encircling walls, visitors admire the 14 towers that once safeguarded its residents.

Just a short drive away, the iconic skyline of San Gimignano rises in the distance, its preserved medieval towers a testament to the town’s prosperous past.

Visitors can wander through the narrow streets, browse local shops, and sample the region’s renowned Vernaccia wine.

Both towns offer a glimpse into Tuscany’s storied history and captivating beauty.

Indulge in the Flavors of Chianti

After exploring the charming medieval towns of Monteriggioni and San Gimignano, the tour continues with a visit to a boutique winery in the renowned Chianti region.

At the winery, guests embark on a guided tour, learning about the wine-making process and the unique terroir of the Chianti hills.

The highlight is a tasting of the estate’s finest wines, expertly paired with a light lunch showcasing regional Tuscan specialties.

Savoring these flavors amidst the picturesque Chianti countryside provides an immersive experience, allowing travelers to fully appreciate the culinary traditions and local culture of this iconic Italian wine region.