From Rome: Tuscany & Siena With Wine Tasting and Lunch

Tuscany is a dream destination for many, and this tour from Rome promises to deliver an unforgettable experience. Explore the historic city of Siena, marvel at the medieval towers of San Gimignano, and indulge in a tantalizing wine and olive oil tasting paired with a traditional Tuscan lunch. Whether you’re a wine connoisseur or simply seeking a taste of la dolce vita, this small-group adventure might just be the perfect way to learn about the beauty and culture of this iconic Italian region.

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About Your Stay

A full-day small-group tour from Rome to Tuscany, visiting Siena and San Gimignano with a wine tasting and authentic Tuscan lunch.
Includes round-trip fast train transportation from Rome to Florence and private minibus transfers to explore the Tuscan countryside.
Guided walking tour of Siena and a quick stop at the medieval town of Monteriggioni, a filming location for "Gladiator".
Enjoy a wine and olive oil tasting experience at a local Tuscan winery, accompanied by an authentic regional meal.
Comfortable and enjoyable experience, with the flexibility to stay longer in Florence at the end of the tour.

You can check availability for your dates here:

Tour Overview

The tour offers a packed day of exploration in Tuscany, featuring stops in the historic cities of Siena and San Gimignano as well as a wine tasting experience at a local winery.

A packed day in Tuscany, visiting historic Siena and San Gimignano, along with a local winery for wine tasting.

Priced from $293.78 per person, the 14-hour small-group tour departs Rome at 6:45 AM and returns around 8 PM.

Participants will travel by fast train to Florence, then explore the region by minibus.

The tour includes guided walks, free time for lunch and shopping, a winery visit with tastings, and an authentic Tuscan meal.

Cancellation is free up to 24 hours in advance.

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Itinerary Highlights

The tour departs Rome at 6:45 AM and travels via fast train to Florence, where participants board a minibus to explore the highlights of Tuscany. First, they’ll enjoy a guided walking tour of Siena, followed by free time for lunch and shopping. Next, they’ll make a quick stop in Monteriggioni, a medieval town featured in the film "Gladiator." The final destination is San Gimignano, known as the "Manhattan of Tuscany" for its distinctive towers. The day concludes with a wine and olive oil tasting at a Tuscan winery, where guests will savor an authentic local meal.

| Destination | Duration | Highlights |

|————-|———-|————|

| Siena | 2 hours | Guided walking tour, free time |

| Monteriggioni | 30 mins| Quick visit, Gladiator filming location |

| San Gimignano | 1 hour | Medieval towers, world-champion gelato |

| Tuscan Winery | 1+ hour | Wine & olive oil tasting, Tuscan lunch |

Included Services

This tour includes a variety of services to enhance the Tuscany experience.

You’ll receive round-trip train tickets between Rome and Florence. A private minibus will transport you through the Tuscan countryside. An English-speaking guide will lead the way and provide insights.

The highlights include a walking tour in Siena, a quick stop in Monteriggioni, and an hour to explore San Gimignano.

You’ll also enjoy a wine and olive oil tasting complemented by an authentic Tuscan lunch.

With the logistics handled, you can focus on savoring the sights, flavors, and culture of this beautiful region.

Important Information

To ensure a comfortable and enjoyable experience, it’s recommended to wear comfortable shoes, bring sunscreen, and dress casually for the tour.

The train travel between Rome and Florence is independent, so tour you will receive their train tickets via email. While no refunds are provided for missed trains, the tour requires a minimum of 3 participants to proceed.

Travelers can opt to stay longer in Florence and take a later train back to Rome if desired, providing more flexibility.

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Customer Feedback

According to reviews, customers have overwhelmingly positive experiences with this Tuscany and Siena wine tasting tour. The tour boasts an impressive 4.8/5 rating based on 5 reviews. Travelers highlight the amazing trip, knowledgeable guides, and enjoyable activities, though some wished for more inclusive costs. One reviewer noted, "The best part was the wine tasting and lunch at the winery. The views were breathtaking."

| Positive Experiences | Negative Feedback |

| — | — |

| Amazing trip | More inclusive costs |

| Knowledgeable guides | Limited gelato coverage |

| Enjoyable activities | |

| Stunning winery views | |

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Departure and Destinations

The tour departs at 6:45 AM from Rome, with travelers taking the fast train to Florence.

Once in Florence, the group boards a minibus and heads to the medieval town of Siena. There, they’ll take a 2-hour guided walking tour and have free time for lunch and shopping.

Next, they’ll visit the walled town of Monteriggioni, a filming location for "Gladiator."

The final stop is San Gimignano, known as the ‘Manhattan of Tuscany’ for its iconic towers. After an hour exploring, the group heads to a Tuscan winery for wine and olive oil tasting, plus an authentic Italian lunch.

Siena Walking Tour

After arriving in Siena, the group embarks on a 2-hour guided walking tour of the historic city.

The knowledgeable guide leads them through the charming medieval streets, pointing out key landmarks:

The grand Siena Cathedral, known for its distinctive black and white striped marble facade
Piazza del Campo, the iconic shell-shaped square and the site of the famous Palio horse race
The Torre del Mangia, a towering bell tower offering panoramic views of the city
Narrow alleyways lined with cafes, boutiques, and centuries-old architecture

The tour provides insight into Siena’s rich history and cultural traditions, whetting the appetite for the next stop on the Tuscan adventure.

Tuscan Wine Tasting and Lunch

After the guided tour of Siena, the group hops aboard the minibus and heads to a renowned Tuscan winery.

At the winery, they’ll get to taste a selection of the region’s finest wines and sample extra virgin olive oil. The expert staff leads them through the tasting, sharing insights into the winemaking process and the unique flavors.

Paired with an authentic Tuscan lunch, the wine tasting is a highlight of the day. Refueled, the group departs for the final stop in the medieval town of San Gimignano, famous for its towers and world-renowned gelato.

Questions About Your Stay

Can I Request a Vegetarian or Gluten-Free Meal Option?

Yes, you can request a vegetarian or gluten-free meal option. The tour company should accommodate dietary restrictions if you let them know in advance. Just be sure to specify your needs when booking the tour.

Is There a Discount for Children or Seniors?

The tour doesn’t offer any discounts for children or seniors. All participants, regardless of age, pay the same price. However, the small group size and flexible nature of the tour may be suitable for families or older travelers.

Can I Make Stops Along the Way for Photos or Extra Time?

Yes, the tour allows for some flexibility. You can make stops along the way for photos or extra time, though the schedule is fairly tight. The tour leader can likely accommodate minor adjustments if requested in advance.

How Many People Typically Join the Tour Group?

The tour group is typically small, limited to 8 participants. This allows for a more personalized experience and easier coordination of stops along the way. The small group size is a key feature of this tour.

Is There an Option to Extend the Stay in Florence or Siena?

Yes, the tour offers flexibility to extend one’s stay in Florence with a later train back to Rome. This allows travelers to spend more time exploring the city at their own pace.

Final Verdict On This Stay

This Tuscany and Siena tour from Rome promises a memorable day. Explore the medieval towns, savor local wine and cuisine, and learn about the region’s rich history and culture. It’s an excellent way to experience the best of Tuscany in a small group setting. With an early departure and a full itinerary, it’s a convenient and comprehensive day trip from the capital.