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Discover Tuscany's charm on this small-group day trip from Florence, featuring wine tastings, visits to Montepulciano and Pienza, and scenic countryside views.
The From Florence: Tuscany Hills Small Group Wine Tour offers a full-day escape into the heart of Tuscany, ideal for those who want to combine wine tasting, historic village visits, and breathtaking landscapes. Priced with a full-day itinerary, it departs from Florence and explores notable destinations such as Montepulciano, Pienza, and Montalcino, with guided wine tastings at two local wineries. The tour lasts approximately 12.5 hours, making it a satisfying yet manageable way to experience Tuscany’s famous wine regions and medieval towns. With over 350 reviews and an average rating of 4.3 out of 5, it’s clear this tour appeals to travelers seeking a comprehensive and relaxed day in Tuscany, though some reviews note long travel times and busy schedule as considerations.
Most importantly, this trip is focused on wine lovers and those interested in Tuscany’s scenic beauty. It’s suitable for those who don’t mind a full schedule and moderate walking, but it’s not designed for wheelchair users or travelers seeking accessible options. This tour balances cultural exploration with wine education, offering a well-rounded experience for visitors eager to see Tuscany beyond Florence’s city streets.


This tour begins at one of two meeting points in Florence, either Via dell’ Oriuolo or a nearby location, depending on the booking option. The bus departs for Tuscany and returns later in the day, with drop-offs at the same meeting points. The group size is small enough to keep the experience intimate, and the coach ride lasts around 2.33 hours to reach the first destination.
The tour concludes with a scenic drive back to Florence, arriving after approximately 2 hours of travel. Travelers should be prepared for a long day, but the comfortable transportation and engaging guides help make the experience enjoyable from start to finish.
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Montepulciano and Pienza are the main highlights of this tour, both celebrated for their Renaissance architecture and picturesque streets. In Montepulciano, visitors enjoy free time to explore, take photos of historic churches, and stroll through charming lanes. The town also features a famous film saga setting, adding a touch of cinematic charm.
In Pienza, architectural beauty and spectacular views of the Val d’Orcia create an atmosphere straight out of a storybook. The town offers ample opportunity for independent exploration and lunch before heading to the next destination. Both towns are known for their atmosphere and scenic appeal, with some reviews mentioning shorter visits due to the busy schedule, but still appreciating the stunning scenery and cultural richness.

This tour features two wine tastings at carefully selected wineries, each offering a variety of local wines. The first cellar showcases three different types of wine, helping visitors understand the differences in taste and texture. The experience includes olive oil tasting with home-produced olive oil and Tuscan bread, adding depth to the understanding of local produce.
The second winery visit in Montepulciano emphasizes Nobile di Montepulciano, one of Tuscany’s esteemed wines, paired with traditional snacks. Many reviews highlight the generous tastings and the knowledgeable guides who explain the winemaking process and regional specialties. The wine experiences are described as very enjoyable, often cited as a highlight of the day.

Driving through Val d’Orcia, the tour offers stunning panoramic views of rolling hills, cypress trees, and medieval villages. The area’s landscape is UNESCO World Heritage Site status, recognized for its unique harmony of nature and human activity. Stops in Pienza allow visitors to absorb the scenery, with plenty of photo opportunities.
The scenic views are a major draw, inspiring poets and artists for generations. While the time in Pienza might be brief, the visual impact of the landscape remains memorable. This part of the tour emphasizes Tuscany’s natural beauty, complemented by visits to age-old towns that showcase historical architecture.
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The tour is led by experienced guides who are praised for their knowledge, friendly attitude, and multilingual skills in English, Spanish, and Italian. Some reviews mention guides like Marco, Luca, and Alessandro, who go above and beyond—translating, providing local tips, and helping capture memories.
Transportation involves comfortable, air-conditioned coaches with small group sizes, ensuring a personalized atmosphere. The long bus rides are inevitable, but the scenic drives and informative commentary help pass the time. Some travelers note delays or long travel times, but overall, the quality of transport and guiding receive positive remarks.

Lunch in Pienza allows for independent exploration and the chance to enjoy local cuisine. Many participants appreciate the free time to shop for cheese, wines, and souvenirs. The tour includes traditional snacks paired with wine, enhancing the tasting experience.
While some reviews mention shorter visits or difficulties finding places open, most find the opportunity to purchase some of Tuscany’s finest cheeses and wines worthwhile. The food tasting at wineries features Tuscan bread and local snacks, adding a culinary dimension to the day.

This tour involves walking through medieval towns, which can include steep hills and uneven streets. Guests are advised to wear comfortable shoes and clothing suited for walking and outdoor sightseeing.
Unfortunately, the tour is not accessible for wheelchair users, and pets are not allowed. Travelers should be prepared for a full day of sightseeing and moderate physical activity.

While the tour offers a balanced schedule of sightseeing, wine tasting, and free time, some reviews mention long bus rides and short visits in towns. The pacing is generally considered good, but it requires patience and willingness to sit on a coach for extended periods.
The guides’ enthusiasm and knowledge significantly enhance the experience, compensating for the busy schedule. Many find the scenery, towns, and wines worth the full-day commitment.

This small-group tour is ideal for wine enthusiasts and culture lovers who want a rundown of Tuscany’s wine regions and medieval villages. It’s perfect for travelers who don’t mind a long, full day and appreciate guided experiences that combine scenery with tastings.
Those seeking more flexibility or shorter visits might find it less satisfying, especially given some reviews about short stops and travel times. However, excellent guides and beautiful destinations make this a worthwhile trip for many.
This tour delivers a well-rounded introduction to Tuscany’s landscapes, towns, and wines. The quality of the wine tastings, knowledgeable guides, and picturesque stops stand out as key strengths. The full-day schedule offers an immersive experience, but it does require patience with travel times.
It suits travellers interested in wine, history, and scenic drives, willing to devote a long day to exploring. The small group size fosters a friendly atmosphere, and the scenic countryside provides stunning photo opportunities. For those looking to sample Tuscany’s best wines and see iconic towns, this tour offers good value and memorable moments.
How long is the tour?
The tour lasts approximately 12.5 hours, including travel, sightseeing, and tastings.
Where does the tour start and end?
It begins at either Via dell’ Oriuolo or a nearby Florence location, with drop-offs at the same spot.
How many wineries are visited?
Visitors enjoy two winery visits, each with wine tastings and local snacks.
Is the tour accessible for wheelchair users?
No, this tour is not suitable for wheelchair users due to the walking involved in towns.
Can I buy wine and cheese during the tour?
Yes, there are shopping opportunities at wineries and in towns to purchase regional wines and cheeses.
What should I bring?
Comfortable shoes and clothes are recommended, as walking and outdoor sightseeing are involved.
Are there vegetarian options?
The provided data does not specify dietary accommodations.
Is there free time at each stop?
Yes, travelers have free time in Montepulciano, Pienza, and Montalcino to explore, shop, and dine.
How many people usually join the tour?
It operates as a small group with fewer participants for a more personalized experience.
What is the main highlight of this tour?
The tour’s wine tastings, stunning scenery, and visits to historic towns are its key features.