Journey through medieval towns, rolling vineyards, and sun-kissed countryside on a guided walking tour. Explore Siena, Chianti, San Gimignano, and the breathtaking Val d’Orcia at a relaxed pace, with enriching local encounters. Enjoy farm-to-table cuisine at rustic trattorias, paired with occasional live music. Stay in charming family-run hotels and engage with artisans and winemakers for an authentic experience. Choose between small group or private excursions for a personalized Tuscan adventure filled with culture, flavors, and unforgettable memories.
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Gianni S. is the provider of this trip
The provider speaks: English
I’m Gianni, owner and guide of the company. I am a Ph.D. geologist with over two decades of experience in the realm of guided walking tours in Italy. For the past 22 years, I’ve dedicated myself to crafting remarkable journeys through this enchanting country. Hailing from Siena, a captivating medieval town nestled in the heart of Tuscany, Italy, I remain firmly rooted here. The allure of this exquisite place has held me steadfast, and it’s from here that I continue to operate and shape unforgettable experiences.
Tour highlights
Authentic Tuscan Experiences
Stroll through medieval towns, vineyards, and rolling countryside while engaging with local artisans, winemakers, and chefs for a truly immersive journey.
Culinary and Wine Delights
Savor farm-to-table meals, enjoy exclusive wine tastings in Chianti and Montalcino, and learn the secrets of Tuscan cuisine in hands-on cooking classes.
Scenic Walks and Cultural Treasures
Explore iconic sites like Siena, San Gimignano, and Pienza, with breathtaking hikes through wheat fields, olive groves, and vineyards, all complemented by expert storytelling.
Route details
Day 1
Rendezvous in Siena: Unveiling the City’s Charm
Meet at the hotel lobby at 4:00 pm to begin your Tuscan adventure with an insightful tour introduction. Accompanied by an expert art guide, explore Siena’s hidden gems—from the captivating Piazza del Campo to charming alleys and the historic Palio horse race district’s museum. Conclude the evening with a delightful dining experience at Babazuf, a family-owned gem where Marco and Chef Giovanni masterfully blend tradition with modern Italian flavors.
📍 6 km / 3.7 miles (leisurely town stroll)
🏨 La Villa Hotel – Siena
🍽 Dinner included
Day 2
A Day in Chianti – Vineyards, Flavors and Culinary Delights
Day 3
San Gimignano – Towers, Trails and Farmhouse Flavors
Day 4
Montalcino and Pienza – Wine, Walks and Tuscan Flavors
Day 5
Bagno Vignoni and San Quirico d’Orcia – Thermal Springs and Tuscan Traditions
Day 6
Monticchiello – Saffron, Cheese and a Grand Farewell
Day 7
Departure Day – Farewell
Difficulty
Moderate
Does not require physical training but involves moderate physical activity
Tour provider's comments
A walk rating of 2+ on a scale from 1 to 5 typically indicates that the walk or hike is of moderate difficulty, but slightly easier than a full 3 rating. Here’s a breakdown of what this might mean:
- Terrain: The terrain may be uneven, with some inclines or obstacles, but generally manageable for most people with moderate fitness. There could be a mix of flat and mildly challenging sections.
- Distance: The distance is not overly long but might require more time than an easy walk. This could be somewhere between 3 to 5 miles (5-8 km), though it varies depending on the setting.
- Elevation gain: There could be some uphill or downhill sections, but nothing too steep or sustained. The elevation changes would be noticeable but not strenuous.
- Skill level: It would be suitable for beginners looking to challenge themselves slightly, or for intermediate walkers looking for a more relaxed outing.
Accommodation
Comfort
Upscale
Hotel
6 nights
6 nights
Hotel
6 night stay at small hotels (3 and 4 stars). Book early and we will try to accommodate you in a room with a view.
Very comfortable to stylish – ensuite bathroom.
Tickets to group meeting place
Group meeting place
Siena
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Partnered with
Weather during the tour
Weather conditions along the route
You will get a weather forecast for this tour’s route based on
- the forecasts for this season
- the statistics from previous years’ trips
Tour conditions
Included
- 6 night stay at small hotels (3 and 4 stars);
- all breakfasts, 5 lunches, 4 dinners. Local wine is always included with lunches and dinners. Vegetarian? Vegan? No problem!;
- transportation along the tour;
- we carry your luggage from hotel to hotel;
- 1 local guide for groups smaller than 10 (groups larger than 10 people will be guided by 2 local guides);
- entrance tickets for all the special events;
- Chianti wine tasting and winery visit: you will talk to the owner;
- learn about saffron making or cheese making (according to availability) at a small farmhouse in Pienza;
- learn how to tell the quality of extra virgin olive oil along an olive oil tasting;
- full cooking class in an ancient building;
- all taxes.
Extras
- transportation to the starting place and from the ending place of your trip;
- tips for the guides;
- 2 dinners when you are on your own along the tour;
- single supplement.
Group size
From 2 to 12 tourists
Duration
7 days
6 nights
It's important to know
Personal equipment you need for the tour
- Walking shoes with good traction (sometimes we might have mud on the trail)
- Hat, Swimming suit, sun cream, water bottle to refill with tap water
- Dinners at Italian restaurants do not require any special dress code.
Wear shoes with good traction
Cancellation of booking
Dates and Prices
- from15 – 21 Jun7 days 6 nights
- from7 – 13 Sep7 days 6 nights
- from7 – 13 Oct7 days 6 nights
