A day in Tuscany & Medieval Towns

If you’re considering a day trip to Tuscany from Florence, chances are you’ve come across several options. This particular private tour of Tuscany and medieval towns has garnered perfect 5-star reviews and recommendations from 100% of travelers—quite the endorsement. It’s designed for those who want to experience the region beyond the usual tourist spots, with a local guide showing you the hidden corners that Italians love to frequent.

What caught our attention about this experience? First, the personalized nature of the tour — it’s just your group, which means flexibility and a more intimate feel. Second, the emphasis on local favorites, from tucked-away villages to authentic wineries and restaurants. However, a possible consideration is the cost, which hovers around $1,022 for up to 8 people. While this might seem steep at first glance, the value lies in the customized, worry-free experience and the chance to explore Tuscany with a knowledgeable guide who’s on your wavelength.

This tour is ideal for travelers who want a relaxed, personalized day exploring Tuscany’s less-touristed spots, especially if you’re after local flavor, scenic views, and a taste of Italian countryside life. If you’re traveling with friends or family and prefer not to drive yourself, this could be a perfect fit. Keep in mind, if you’re looking for an organized, guided experience that takes the hassle out of logistics, this tour checks those boxes well.

Key Points

• Private, customizable experience tailored to your group’s interests
• Hassle-free transportation with pickup and drop-off included from Florence
• Local guidance providing authentic insights into Tuscany’s hidden gems
• Visit medieval towns and off-the-beaten-path spots most travelers miss
• Includes a recommended lunch at a traditional restaurant (own expense)
• Ideal for those wanting a relaxed, immersive day without the stress of planning

What You Can Expect from This Tuscany & Medieval Towns Tour

This is a full-day adventure that usually lasts around 8 to 9 hours, with the core goal of showing you the scenic, historical, and culinary treasures of Tuscany in a relaxed setting. What makes this tour stand out is its focus on hidden spots—places that most visitors never see, even on popular group trips. Your driver-guide is a local, and they are ready to share tips and recommendations, making the day more personal and authentic.

Pickup and Transportation

The tour kicks off with pickup from your accommodation in Florence, which means you won’t need to worry about navigating or parking. The vehicle? An air-conditioned private car, making the long drive comfortable, especially if you’re traveling with a group. Several reviews highlight how the vehicle’s comfort and the driver’s professionalism made the experience enjoyable from the start.

The Route and Stops

The itinerary is flexible, but the emphasis is on off-the-beaten-path towns and regions that locals love. While the exact schedule varies, you’ll likely visit medieval villages and perhaps wine country, depending on your driver’s recommendations. Travelers have loved the chance to explore towns like Lucca and San Donato, and the reviews praise the guides’ knowledge and ability to craft a personalized day.

One reviewer shared, “Alberto was a wonderful guide and driver. We started in Livorno and drove to Lucca and then to San Donato to one of our favorite restaurants in the world, La Toppa.” This shows how flexible and tailored the experience can be, and how guides really try to make the day memorable.

Food and Wine

The tour includes a lunch reservation at a traditional restaurant, which you pay for separately. It’s an opportunity to savor authentic Tuscan cuisine. Several reviews mention the wineries and restaurants as highlights—one reviewer called their winery lunch “delicious,” and others appreciated the local wine tastings. Guides often help with wine recommendations, ensuring you’re sampling some of the best regional offerings.

Hidden Gems and Off-the-Beaten-Path Spots

Most travelers love discovering medieval towns and lesser-known villages, away from the crowds. A reviewer noted, “Gianmaria instantly makes you feel welcome and like you’re visiting a friend,” which underscores the friendly, intimate vibe of the tour. These spots are not just scenic; they’re steeped in history and local character, making your day feel genuine and immersive.

Guides and Personal Service

The reviews are filled with praise for the guides—Gianmarie, Francesco, Claudio—who are described as knowledgeable, friendly, and professional. One reviewer shared, “Francesco made our experience unforgettable! He had so much knowledge to share about the region,” emphasizing how much the guides contribute to the experience.

Cost and Value

While $1,021.75 might seem hefty, especially for a group of eight, the value lies in the personalized service and the convenience of transportation and expert guidance. Comparing this to the cost of booking separate taxis, meals, and entry fees, the price becomes more understandable. The reviews suggest that many guests felt the experience was worth every penny, especially considering the quality of the guides and the exclusive access to local treasures.

In-Depth Look at the Itinerary

Since the itinerary is flexible and tailored, here’s a typical breakdown based on reviews and the tour description:

Morning: Departure and First Stop

You’ll be picked up early in the day from Florence, heading straight into the Tuscan countryside. The drive itself is part of the joy, with scenic views rolling past the window. Your guide will share insights about the area’s geography, history, and local customs—making the drive feel like a relaxed, informative chat.

Mid-Morning: Medieval Towns

Expect to visit medieval villages that most travelers never see. For example, one reviewer mentioned visiting two medieval towns and ending with a wine tasting at a family-run winery. These towns usually feature cobbled streets, ancient walls, and charming plazas—perfect for wandering and taking photos.

Lunch Break

Your guide will organize a reservation at a traditional Tuscan restaurant, which you’ll pay for separately. The reviews mention that the meal was a highlight, with delicious local dishes and wine. Guides often help with wine recommendations, adding a layer of expert tastings to your day.

Afternoon: Hidden Spots & Wineries

Post-lunch, you might visit a winery for a tasting, often at a family-run estate. The reviews describe these experiences as “delicious” and “fabulous,” with some guides also offering wine suggestions based on their regional expertise.

Late Afternoon: Scenic Drives & Return

As the day winds down, your driver will take you back through picturesque landscapes, possibly stopping at more tiny towns or scenic viewpoints for photos. The journey back to Florence is a relaxing conclusion, with plenty of time to reflect and share impressions.

What the Reviews Say

Many comments praise the knowledge and friendliness of the guides. One reviewer called their guide “the best driver in Italy,” and others appreciated the flexibility and personal touch. They also highlight how the guides go above and beyond—making restaurant reservations, sharing recommendations, and making everyone feel at home.

The “great ride and guide” reviews underscore how important the vehicle, driver, and guide are to the overall experience. Several travelers found the day to be “the highlight” of their trip, especially mentioning the wine tastings and medieval towns as standout moments.

A common theme is the feeling of insider access—visiting places that are not crowded, tasting authentic local food, and learning from passionate guides. This tour clearly appeals to those who want more than just a cookie-cutter trip, valuing genuine connections and regional expertise.

Practical Considerations

• Price: At just over $1,000 for up to 8 people, it’s a good deal if you’re traveling with friends or family and want a private experience. It’s a convenient all-in-one option for transport, guiding, and exclusive visits.
• Duration: Around 8–9 hours, so be prepared for a full day—comfortable shoes and relaxed expectations are key.
• Booking: The tour is booked on average 42 days in advance, so plan ahead if you want to secure a spot.
• Cancellation Policy: Free cancellation up to 24 hours before, offering some flexibility if your plans change.

Who Should Book This Tour?

This is a great pick for those who want a tailored, intimate experience of Tuscany’s countryside and medieval towns. If you prefer not to drive, love good food and wine, and enjoy storytelling from passionate guides, you’ll find this tour well worth it. It’s perfect for travelers looking to escape the crowds, explore local favorites, and enjoy a leisurely day with all logistics handled for you.

If you’re traveling with friends or family and want a private, customizable day, this tour hits the mark. However, if you’re on a strict budget or prefer self-guided exploration, you might want to consider other options.

FAQs

Is transportation included in the tour price?
Yes, you’ll be picked up from your accommodation in Florence and transported in a private, air-conditioned vehicle throughout the day.

Can I customize the itinerary?
While the tour is flexible, it’s primarily designed to showcase hidden gems and local favorites. Your driver-guide can suggest stops based on your interests.

What about lunch?
Lunch is organized at a traditional restaurant and paid for separately. The guide will help make the reservation, ensuring you enjoy authentic Tuscan cuisine.

Is this tour suitable for children?
Most travelers participate comfortably, but since it’s a full-day private trip, consider your children’s stamina and interest in medieval towns and wine tastings.

How far in advance should I book?
Most bookings are made about 42 days before the trip, so early planning is advised, especially in peak seasons.

What if I need to cancel?
You can cancel up to 24 hours before for a full refund, providing flexible planning options.

Are the guides knowledgeable about the region?
Absolutely. Many reviews highlight guides like Gianmarie, Francesco, and Claudio as being highly professional and passionate about sharing their region.

Is the experience worth the cost?
Given the personalized service, exclusive visits, and local insights, many guests feel the experience offers good value—especially for groups seeking a hassle-free, memorable day in Tuscany.

If you’re after a relaxed, authentic taste of Tuscany that goes beyond the usual tourist routes, this private tour offers a compelling package. With expert guides, scenic drives, and insider visits, you’ll get a real feel for what makes Tuscany special—its medieval charm, local flavors, and breathtaking landscapes.

It’s best suited for travelers who value comfort, personalization, and regional knowledge. The price might be a consideration for some, but many find the experience well worth it for the quality and convenience. Whether you’re a history buff, wine lover, or just eager to see the lesser-known towns, this tour can deliver a memorable slice of Italy’s heartland.

Enjoy your Tuscan adventure—exploring the hidden side of Italy with the comfort and insights that make a trip truly special.