Tuscan Getaway

Difficulty

Moderate

Comfort

Upscale

Immerse yourself in the heart of Tuscany, a 5-day journey through rolling vineyards, medieval villages, and cypress-lined hills. From Siena’s Renaissance beauty to the breathtaking Val d’Orcia, every step feels like a living postcard. Indulge in authentic flavors at family-run trattorias, sip world-class Chianti wines, and experience the warmth of Tuscan hospitality. We’ve distilled the best of our 7-day tour into an unforgettable experience, blending art, history, and the Italian way of life. More than a trip, this is a journey of connection—where friendly locals, passionate winemakers, and skilled artisans turn moments into lifelong memories. Join us and discover Tuscany, not just as a destination, but as a way of living.

Price (in euros) for the tour depends on the occupancy number of your private group:
2-3 - 3690 pp; 4-5 - 3190 pp; 6-7 - 2990 pp; 8-9 - 2890 pp; 10-11 - 2790 pp; 12 and more - 2690 pp.

Hiking and Trekking

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 Encounters

Meet passionate locals, from a NYTimes Bestselling author in Chianti to dedicated farmers and artisans, bringing Tuscany’s rich traditions to life.

Flavors of Tuscany

Indulge in farm-to-table dining, from truffle-infused pici pasta and world-class Chianti wines to handcrafted pecorino cheese and saffron-infused delicacies.

Scenic Walks and Hidden Gem

Wander through rolling wheat fields, medieval villages, and cypress-lined paths, uncovering the beauty of Siena, Val d’Orcia, and Monticchiello on foot.

Route details

At 4:00 pm, we gather in the hotel lobby to begin our Tuscan adventure with an engaging tour introduction. Accompanied by an expert art guide, we’ll explore Siena’s timeless wonders, from the iconic Piazza del Campo to its charming labyrinth of medieval alleys and the fascinating Palio horse race district museum. As the evening unfolds, we indulge in an exquisite dinner at Babazuf, a beloved family-owned restaurant where Marco and Chef Giovanni masterfully blend tradition with contemporary Italian flavors.

🚶‍♂️ 6 km / 3.7 miles (town stroll)
🏨 La Villa Hotel – Siena
🍽️ Dinner included

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

4 nights

4 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

4 night stay at small hotels (3 and 4 stars). Book early and we will try to accommodate you in a room with a view;
all breakfasts, 3 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;
local guide;
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;
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;
single supplement.

Group size

From 2 to 12 tourists

Duration

5 days

4 nights

It's important to know

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