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Tuscany Classic Walk

(1 customer review)

Tuscany has something for everyone: historical hilltop towns, delicious food and wine, rolling fields of vineyards and olive trees, and a warm hospitality. Start in Florence and then spend six days experiencing the best the region has to offer.

Duration: 7 nights / 8 days
Dates: Available upon request, contact us for details
Trip starts/ends: Florence / Chiusi train station
Activity level: 2-3 easy to moderate walking (other activity options available) [more info]
Group size: min 4 - max 14


  • guided walk in the Florentine hills or casual city walk
  • 6 guided walks through Tuscany
  • visit of the medieval towers of San Gimignano
  • wine-pairing lunch at a local producer of Vernaccia
  • guided visit of the beautiful city of Siena
  • pecorino cheese and olive oil tasting
  • visit of the open-air thermal baths at Bagno Vignoni
  • wine-tasting in Montalcino
  • 7 nights in charming accommodations

Trip price includes

  • 7 nights accommodation in 3 and 4 stars hotels
  • all breakfasts
  • 2 wine-tasting lunches
  • 5 dinners
  • guided visit of Siena
  • visit to cheese farm and tasting
  • all transfers and luggage transfers as per itinerary

Not included

  • 5 lunches and 1 dinner
  • drinks other than water at meals
  • activities not listed in the itinerary


Day 1: Arrival in Florence

Independent arrival in Florence. We haven’t scheduled a meeting this evening to allow for relaxed arrivals, so you’re free to arrange your own dinner (we’re happy to provide suggestions!). Overnight Florence. Dinner not included.


Days 2-4: San Gimignano Area

Follow your guide this morning to explore the highlights of Florence before heading to the countryside; OR – for those who have already spent time in Florence – head into the hills for a lovely morning walk through the narrow lanes and woods above the city. Spend the next 3 nights near the fascinating city of San Gimignano, whose 14 Medieval towers still remain from an original 72. You also visit the nearby hilltop town of Volterra, which was an important Etruscan city 2,500 years ago, as well as fabulous Siena, which rivaled Florence for control of trade and banking in the region for centuries. We offer beautiful walks each day to accompany the cityscapes, though any of our tours could become “light active” where you add more cultural experiences in place of the walks. 3 nights near San Gimignano.


Days 5-7: The Val d’Orcia and the landscapes of the Crete Senesi

We head south today into the iconic scenery of the Orcia river valley (the Val d’Orcia), whose vast wheat fields billow with green in the spring and spread out in browns and tans in the fall. Every view is dotted with cypress trees and the occasional stone farmhouse as we explore the historical hilltop towns nearby. See Pienza, former home to Pope Pius II and now the center of pecorino (sheep’s milk) cheese production, and Bagno Vignoni, whose natural thermal waters bubble up right in the town square. We’ll make sure to try plenty of the region’s world-famous food and wine too! 3 nights near Pienza.


Day 8: Tour Ends

We offer one group transfer to the Chiusi train station (on the line to Florence and Rome), or if your guide is driving back to Florence you can hitch a ride with them.


Getting there and away: You can fly directly into the Florence airport, which is well connected to a variety of European hubs, or take a train from Rome or Milan. Chiusi is also on a train line for easy onward connections.

1 review for Tuscany Classic Walk

  1. Mikel Moore

    While our time with Manu and Claire was part of a private departure, our travel included Florence, San Gimignano, Siena and Pienza. Traveling with Manu and Claire is, for us, traveling with trusted friends. This is our highest possible praise.
    Manu and Claire tend to all the details, provide the transportation, speak your language and Italian (along with other languages), share their knowledge of the places, the people, the food and the wine, expose you to new experiences, and accommodate your interests. They do all of this with efficiency and a smile. With guides like these, you are free to enjoy each moment and truly relax.
    The Wild Sage itineraries work perfectly for us. They include exercise, sightseeing, unique experiences, and time for relaxation and reflection. We found that every day included something memorable and special. Often these elements were part of Manu and Claire’s plan. At times they were unexpected and magical.
    Manu and Claire also worked with us to shape the travel itinerary we wanted for a private departure. With their help we were able to have exactly the trip we were hoping for, enhanced by their scouting, knowledge, and suggestions. We could ask for nothing more.
    We are already daydreaming about and planning our next adventure with Manu and Claire.

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