Active travelers who value independence and flexibility will appreciate this self-guided tour through the Tuscan countryside. Opt for a leisurely pace, or more involved hikes, as you first see the masterworks of Florence—the birthplace of the Renaissance—and then make your way to Chianti. You won't want to miss tasting some of the region's famous vintages, with Cypress tree views all around you. End your journey with an exploration of the preserved medieval city of Siena for a trip back in time.


  • Be wowed by Renaissance masterpieces in Florence
  • Sip on some of the most famous wines in the world in Chianti
  • Stroll through picturesque farms in Radda in Chianti
  • Marvel at the architectural grandeur of Siena

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Florence Florence
Day 2 Settignano to Fiesole Florence
Day 3 Greve in Chianti Greve in chianti
Day 4 Panzano Greve in chianti
Day 5 Radda in Chianti Radda in Chianti
Day 6 Radda in Chianti Radda in Chianti
Day 7 Siena Siena
Day 8 Departure via Florence  

Detailed Itinerary

Day 1: Arrive in Florence

Florence, the birthplace of the Renaissance
A view of historic Florence

Welcome to Italy! When you land in Florence Airport, Peretola (FLR), a driver will be waiting to take you to your hotel in the middle of the city. After you check in, you'll be free to explore the birthplace of the Italian Renaissance on your own. If you'd like, you can book a self-guided walking tour that will start and end at the city's hub of activity—Piazza della Signoria. We recommend having dinner at one of the city's countless quality restaurants or trattorias before returning to your hotel for the evening.

Day 2: Settignano to Fiesole

View of Florence from Fiesole
View of Florence from Fiesole

Today, you'll venture into the hills above Florence, where it is believed that Leonardo da Vinci tested his famous flying machine. You'll take a 25-minute bus ride up to the village of Settignano, and then begin your walk to the small town of Fiesole. Along the way, you'll have beautiful views of cypress trees, olive groves, and Florence's red-tile-roofed skyline below. In Fiesole, you can tour its Etruscan ruins and Franciscan monastery.

Day 3: Greve in Chianti

Chianti, one of Italy's most famous wine-growing regions
Chianti, one of Italy's most famous wine-growing regions

One of Tuscany's most famous areas, Chianti, is your destination today. From Florence, you'll travel either by bus or a private transfer 16 miles (27 km) south to Greve in Chianti. There, you'll find the capital of the Chianti wine-producing region. After you settle into your hotel, you might explore the local outdoor market, or begin your sampling of the region's more than 50 wines. 

You'll have two walking tours to choose from: 

Walk A: Greve in Chianti loop via Uzzano
Start from Greve in Chianti's main piazza, traveling through the Chianti Classico area passing by Villa Calcinaia and numerous vineyards or “aziende agricole” where Chianti is produced.

Walk B: Greve loop via Montefioralle
Travel through the forest among dense wild vegetation, villas, vineyards, and olive groves. You will pass by abandoned farms, ruins, and villas, before reaching the panoramic hamlet Montefioralle.

Plan your trip to Italy
Chat with a local specialist who can help organize your trip.

Day 4: Panzano


It's a day of discovery as you make a loop around the town of Panzano. You'll walk through the hills surrounding the area, with a backdrop of Chianti vineyards. Along the way, you'll discover ancient Roman farmsteads. Of course, there will be opportunities to stop and taste more vintages as you enjoy a leisurely day strolling in the countryside.

Day 5: Radda in Chianti

Chianti, one of the world's most famous wine-growing regions
Chianti, one of the world's most famous wine-growing regions

A short car transfer will take you deeper into Chianti, and to the highest of the area's hills — Monte San Michele. You'll start in Badiaccia and then descend through a forested valley of centuries-old chestnut trees, continuing toward the medieval hamlet, Volpaia, which is surrounded by vineyards and a castle. You might stop by a local enoteca (wine bar) for a glass of—what else— local wine, before continuing on to Radda in Chianti.

Day 6: Radda in Chianti


Spend a leisurely day exploring the area, perhaps taking a scenic walk around the center of Radda in Chianti. You might browse the local outdoor market, sip a cappuccino on the piazza, or people watch. Make your way to the hamlet of Vertine for lunch, and in the afternoon, treat yourself to a glass of Chianti at Colle Bereto—a celebrated local vineyard.

Day 7: Siena

Siena, Italy
Siena, Italy

After breakfast, you'll travel 28 miles (46 km) south by bus or a private transfer to the medieval stronghold city, Siena, which is also famous for its “Palio” horse race, held in its shell-shaped Piazza del Campo. You won't want to miss its particular central church, the Duomo, and medieval palaces. You might feel as if you are traveling back in time as you meander through the narrow streets of this historically-significant Tuscan city.

Day 8: Arrivederci Tuscany

Siena, Italy
Siena, Italy

Your itinerary will end after breakfast, but you may want to book extra nights in Siena to continue exploring its museums, galleries, and churches, or enjoying the atmosphere in its central piazza. A visit to the top of its bell tower is also quite a sight that you won't want to miss.


Map of Hiking Through Tuscany: Florence, Chianti, & Siena - 8 days
Map of Hiking Through Tuscany: Florence, Chianti, & Siena - 8 days