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Tuscany Classic Walk

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

Highlights

  • 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

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.

from 2.600 €
[info on prices]

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Activity Levels

Some tours have a range of activity levels through the week, where some walks may be more challenging than others, but this will give you a general idea of the type of walking/hiking involved on your tour.

1 – EASY: City walking, all or mostly paved, minimal climbing
2 – GENTLE: Moderate hills & easy terrain
3 – MODERATE: Some sustained hills with occasional steep grades on a mix of terrains
4 – HIKE: Classic hiking with rough/rocky terrain, sustained hills, and longer mileage
5 – CHALLENGING: Challenging hiking with steep climbs and descents over rocky terrain and some longer mileage

See below for more detail:

1 – EASY: City walking, all or mostly paved, with minimal climbing (though some cities may have steeper inclines). Archaeological sites may be unpaved but the grades and difficulty level is easy. TOURS: Sicily Coast-to-Coast and any “light active” version of a tour

2 – GENTLE: Moderate hills & easy terrain
The terrain is easy to navigate with packed earth or gravel roads. There are some climbs but nothing too challenging. TOURS: Tuscany, Puglia, Provence
[2+ The “plus” indicates more challenging terrain though the walks are gentle].

3 – MODERATE: Some sustained hills with occasional steep grades and rocky terrain
Here you find a mix of terrain with some steep stretches.
TOURS: Corsica, Sardinia, some of the Dolomites tours, and some hikes on the Greek Islands
[3+ The plus indicates rockier terrain or lots of stone steps (Amalfi, the Cinque Terre) or greater elevation gain/loss (the Dolomites)].

4 — HIKE: Classical hiking with rough terrain, sustained hills, and more mileage. These hikes are on a mix of rough terrain, sometimes involving steep stretches and difficult footing. TOURS: some of our hikes in Sardinia, some of the days in the Cinque Terre, some of the variants of our Dolomites tours.

5 – CHALLENGING: Longer days, challenging climbs, rocky terrain. We don’t do a lot of seriously challenging tours but we do have a Dolomites trip where we hike from hut to hut, so that’s probably the closest we get to a 5.

Info on prices

Some prices indicated on our website are for 2023 while others are already for 2024, and they all depend on the number of sign-ups and other factors (hotels, activities, and inclusions that may change with each departure) so please contact us for details.