Starts
Ends
Pisa, Italy
Florence, Italy

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Earn USD 99+ in travel credits.
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25,000+ trip reviews, with an average rating of 4.8 out of 5.
Enjoy short walks in the classic rolling landscapes of southern Tuscany
Spend time in historic hill-top towns and cities of Florence and Siena
Enjoy wine tastings and delicious Tuscan cuisine
Experience the rolling hills and vineyard-dotted landscapes of Tuscany on the Tuscany Walking and Wine tour, an easy-paced 8-day journey created for travelers who appreciate the finer things in life. Starting in Pisa and ending in Florence, this walking tour blends scenic rambles with rich cultural encounters.
Meander through Chianti’s renowned vineyards, explore the sun-drenched medieval towns of San Gimignano, Pienza, and Montalcino, and sample some of Italy’s most celebrated wines—Brunello and Chianti among them. Along ancient pilgrimage paths, you’ll savor local cuisine and fresh produce, refueling your spirit as well as your palate.
The trip includes accommodations in carefully selected hotels, transport, and delicious meals, ensuring a seamless Italian experience. The unique selling point of this tour package is the harmonious combination of gentle hiking and gastronomic pleasure, offering access to Tuscany’s scenic beauty and culinary treasures. For those seeking an indulgent yet active escape, Tuscany Walking and Wine is the perfect getaway.
Itinerary was good. But I would have appreciated being able to see, even at a distance, the leaning tower. I had no wish to visit it. But perhaps a view could have been arranged when we left our Pisa hotel in the taxi?
Super holiday! The walks through the beautiful Tuscany countryside with Cypresses, Olive trees and vines will live with me for ever. Itinerary was perfect with challenging walks and time to relax afterwards. The accommodation was excellent, breakfasts substantial and wine tastings informative and very enjoyable. Definitely 5*!
A very enjoyable trip. Good leader, wonderful scenery and well chosen accommodation.
I enjoyed a great week in Tuscany, nothing was too much trouble for our Explore Leader, Enrico. We had a very delicious wine tasting on Day 2, with a great lunch and we finished the week with an Aperitif overlooking Florence. The hotel in Florence was changed quite late and if you were to have a room on the main street it was quite noisy. If you like walking, wine and food, I would definitely recommend this trip.
The entire experience was terrific ... the itinerary was well-paced and exciting, Tuscany is beautiful and the food was awesome, and best of all our guide AJ was the "star of the show" who made the trip really educational and memorable.