Discover Authentic Tuscany on a Private Tour

Tailor-made e-bike, horseback riding, hiking & wine experiences with a certified local guide.

⭐⭐ ⭐⭐⭐  54+ Five-Star Reviews – Highly Rated on Google & TripAdvisor

100% Private & Custom

Tailored entirely to your pace, schedule, and group preferences.

Door-to-Door Pickup

Complimentary pickup from your villa, hotel, or agriturismo across Tuscany.

Certified Local Expert

Guided by licensed, local English-speaking professionals born and raised in Tuscany.

Private Chianti Horseback Riding, Gourmet Winery Lunch & Wine Tasting

✦ 100% Private & Personalized
✦ Door-to-Door Transport (Pickup at Hotel/Villa)
✦ Guided Countryside Ride & Gourmet Winery Lunch

Ride through scenic vineyards and olive groves with a dedicated instructor, followed by a relaxed wine tasting lunch.

From €290 / person (Exclusive private experience · Min. 2 people)

Private Chianti E-Bike Tour, Gourmet Winery Lunch & Wine Tasting

✦ 100% Private & Personalized
✦ Door-to-Door Transport (Pickup at Hotel/Villa)
✦ Authentic Gourmet Lunch & Fine Wine

Enjoy a seamless e-bike ride through Tuscan hills with a dedicated local guide, tailored to your pace.

From €290 / person (Exclusive private experience · Min. 2 people)

Private Tuscan Cooking Class, Gourmet Villa Lunch & Wine Tasting

✦ 100% Private & Personalized
✦ Door-to-Door Transport (Pickup at Hotel/Villa)
✦ Hands-On Culinary Masterclass & Villa Lunch

Prepare authentic regional recipes and handmade pasta with a private chef, then enjoy your meal paired with fine wines.

From €360 / person (Exclusive private experience · Min. 2 people)

Private Chianti Vespa Tour, Gourmet Winery Lunch & Wine Tasting

✦ 100% Private & Personalized
✦ Door-to-Door Transport (Pickup at Hotel/Villa)
✦ Scenic Countryside Drive & Gourmet Winery Lunch

Ride iconic Italian Vespas along quiet Tuscan roads with a dedicated guide, ending at an exclusive boutique winery.

From €310 / person (Exclusive private experience · Min. 2 people)

Private Chianti Hiking Tour, Gourmet Winery Lunch & Wine Tasting

✦ 100% Private & Personalized
✦ Door-to-Door Transport (Pickup at Hotel/Villa)
✦ Scenic Nature Trail & Gourmet Winery Lunch

Walk breathtaking Tuscan ridge paths with a dedicated local guide, completely tailored to your walking pace.

From €290 / person (Exclusive private experience · Min. 2 people)

Private Silent Disco & Aperitivo: Anywhere in Tuscany

✦ 100% Private & Personalized
✦ Wireless Headphones with Music
✦ Iconic Tuscan Sightseeing & Local Wine Included

Explore Florence or scenic Tuscan towns with a private high-energy silent disco walk, perfect for groups and celebrations.

From €30 / person (Exclusive private experience · Min. 4 people)

Private Tuscan Truffle Hunting, Gourmet Winery Lunch & Wine Tasting

✦ 100% Private & Personalized
✦ Door-to-Door Transport (Pickup at Hotel/Villa)
✦ Authentic Truffle Hunt & Multi-Course Gourmet Lunch

Immerse yourself in Tuscan woods with an expert hunter and trained dogs, followed by a luxury fresh truffle lunch.

From €370 / person (Exclusive private experience · Min. 2 people)

Tailor-Made Adventures & Authentic Experiences in Tuscany

Reviews

Real Experiences, Real Reviews

Posted on Google Google
Samantha Rose Lavin profile picture
Samantha Rose Lavin
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We had an incredible tour of Chianti and Siena with Tom! The tour included wine tasting, an incredible lunch, a few hours in Siena and a stunning scenic drive through the country side. He can tailor the day according to the desires of your specific group. Tom was extremely professional and knowledgeable. He picked us up and dropped us off right by our hotel. His van is clean and comfortable and we felt very safe with him. He went out of his way to show us authentic villages with plenty of time for photos. I highly recommend Tom for a fun, unique and informative tour. He was very kind and speaks perfect English. I will be using him on my next trip and would give 6 stars if I could!!
Posted on Google Google
Emily Mason profile picture
Emily Mason
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Highly highly recommend booking with Tom! We enjoyed a hiking tour as well as the truffle hunting, and these two days were hands down the best part of our entire trip. Tom is so kind and truly cares for his guest experience and will go out of his way to make it memorable. I would not hesitate to book with Tom if you would like an incredibly authentic and fun experience!
Posted on Google Google
Grant Mason profile picture
Grant Mason
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We did two tours with Tom. A hike around Tuscany with a lunch and wine and a truffle hunting excursion. Tom was the perfect host and so wonderful with his time and knowledge of the area. I can’t express how wonderful he was with us.
Posted on Google Google
Verity Elks Riches profile picture
Verity Elks Riches
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Tom is the goat! Couldn’t recommend him more. We had an incredible day spent truffle hunting & wine tasting.
Posted on Google Google
Alice Waterhouse profile picture
Alice Waterhouse
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Tom is a legend, had the best day exploring Tuscany truffle hunting & wine tasting!
Posted on Google Google
Karen McDonald profile picture
Karen McDonald
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The private tour with Tom was FABULOUS!!! We highly recommend if you prefer special treatment. Thank you so much for the wonderful experience.
Posted on Google Google
Melissa Feldhake profile picture
Melissa Feldhake
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Incredible day at a fantastic, small winery with panoramic views of Tuscany. After an informative (off-road) tour in a vintage Land Rover through the vineyard, which had breathtaking views of San Gimignano, we enjoyed an amazing lunch with a paired wine tasting. After, we went to San Gimignano and explored the city with our local guide. We would absolutely recommend!
Posted on Google Google
Melissa Guilbeau profile picture
Melissa Guilbeau
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Our Vespa tour with Tommaso was absolutely fabulous! It was the highlight of our trip. Tommaso was fun, kind and very knowledgeable. I cannot recommend Tuscany by Tom enough. It was worth every penny!
Posted on Google Google
Darin Bradbury profile picture
Darin Bradbury
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Tomaso, was absolutely fabulous. We had a wonderful day, felt like we were local insiders. He was fun, lively, and helpful. He Made our day with him the pinnacle of our two week trip.
Posted on Google Google
Alyssa Malenic profile picture
Alyssa Malenic
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This was our second tour with Tom. Once on our honeymoon in 2024, and now with our toddler and parents! We had the most amazing day each time. We reached back out to Tom when we decided we were visiting Florence again and he was so creative and accommodating to make sure the day was exciting, but doable with a toddler! He picked us up in the morning with a generous gift for our toddler to keep him busy on the drive to our tour. Our son loved it and it was such a thoughtful touch! We started the day harvesting grapes and learning about the winemaking process at a beautiful family vineyard. Then we had a delicious lunch at the most picturesque resort/farm, followed by a super fun and leisurely e-bike ride to a beautiful Tuscan town! We loved that it was all off the beaten path. Tom made sure our son’s peanut allergy was attended to at lunch — attention to every detail! He also took loads of pictures to share with us so we didn’t have to stop and think about taking them ourselves. As someone who is terrible at photography myself, this was so appreciated! Everytime we book a tour with Tom we walk away with it being the best day of our trip, and feeling like we have a friend in Tuscany. 100% recommend Tuscany by Tom to anyone and everyone!!
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About us

Your Local Host for Unforgettable Experiences in Tuscany

Meet Tommaso Degl’Innocenti – Local Expert for Private Tuscany Adventures

Born in Vinci, right in the heart of the Tuscan countryside, Tommaso is a passionate world traveler who has explored 83 countries. Today, he uses that global perspective to design flawless, stress-free vacations back home. As a certified Tour Leader, E-Bike Guide, and horseback riding instructor, he specializes in private outdoor adventures across Florence, the Chianti region, and the hidden gems of Tuscany.

Since 2010, Tommaso has been crafting tailor-made itineraries blending authentic culture, nature, and local traditions. From seamless logistics to unique activities, explore Tuscany with a true local who knows its soul and handles every detail for you!