Tuscany Self-Guided Tours | Italy Vacations

Tuscany

Highlights

Explore hilltop towns among Tuscany's rolling vineyards and farmlands, with stunning panoramic views
Savor gourmet food and wine featuring fresh, organic Tuscan produce like olive oil, pasta, and cheeses
Be immersed in Renaissance Florence with visits to the Uffizi Gallery, Pitti Palace, and lively piazzas
Wander through Siena, a UNESCO Site, famous for Piazza del Campo and its impressive Duomo
Enjoy Tuscany's scenic landscapes with vineyards, olive groves, and cypress-lined hills
Discover Chianti's vineyard-covered hills and savor its renowned wines

Tuscany is world-famous, located in central Italy, and known for its rolling hills, historic cities, and spectacular landscapes that seem straight out of a painting! With Florence as its capital, Tuscany is abundant in art and culture, delicious cuisine, and timeless hilltop villages. Equally well known, especially as a wine-producing region is Chianti. This sub-region within Tuscany is perfect for an active vacation with its own picturesque vineyards and enchanting countryside.

Experience the Best of Tuscany
Our enchanting Tuscany trips invite you to experience beauty firsthand with a selection of hiking and biking adventures that allow you to fully experience the region’s rich culture and impressive landscapes at your own pace.

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Our Tour Types

Hiking in Tuscany

Take a hiking adventure through the timeless landscapes of Tuscany, Italy. Our self-guided tours offer an immersive experience in the scenic settings of Tuscany's rolling hills, vineyards, and historic towns. Spend time under the Tuscan sun, walk through idyllic hilltop towns, enjoy the charm of medieval and Renaissance architecture, relax and explore the cultural heritage.

Cycling through Tuscany

Cycle through the most picturesque regions of Tuscany, Italy. Our biking vacations offer a perfect blend of challenge and discovery, catering to all levels of cyclists. Whether you’re pedaling on your own accord, or relaxing on an e-bike, you’ll cruise through the world-renowned winelands, discovering picture-postcard medieval and Renaissance hilltop villages.

Traveling Tuscany In Style

Enjoy the ‘finer things in life’ by treating yourself to elevated accommodation during your hiking adventure. Tuscany In Style invites you to savor every moment of your travel experience. Stay in a 10th century monastery and dine in a Michelin star restaurant. Pamper yourself with a spa treatment or take a dip in the infinity pool with panoramic views of the rolling Tuscan hills below. With Macs In Style, experience style and upgraded comfort with your hiking adventure.

Tuscany’s Slower Adventures

Slower Adventures combine hiking or biking with free time to experience the cultural at a more leisurely pace. While the active days are certainly still active, they’re generally shorter, allowing for more free time to savor your Tuscan surroundings. Whether you wish to window shop through towns and villages, sample the local wine, visit heritage sites, or relax with an afternoon espresso, the choice is all yours on a Slower Adventure in Tuscany.

Italy’s Pilgrimage: The Via Francigena

This popular pilgrimage connects Canterbury to Rome and passes through Tuscany, which is considered one of the most spectacular stretches of the Camino. Whether walking or biking the route, you’re in for an extraordinary experience that includes an array of cultures, cuisines, contrasting terrains and climates.

Discover Tuscany

Must-Visit Destinations in Tuscany

Florence: Discover world-class art and Renaissance architecture in this vibrant city, the cultural heart of Tuscany.
Siena: Wander through medieval streets and marvel at the stunning Piazza del Campo and the Duomo.
Chianti: Enjoy hiking and biking through scenic vineyards and olive groves in this renowned wine region.
Explore charming hilltop towns and indulge in local wine tastings.
Val d'Orcia: Walk through idyllic landscapes and capture the essence of a Tuscany Italy vacation.
Best Time to Visit Tuscany

Seasonal Highlights
Tuscany is popular year-round – So make sure you book as far in advance as possible to ensure availability for specific dates

April-June: Mild weather and blooming landscapes make it ideal for biking and hiking
July-Aug: Historic towns and villages are abuzz, yet the weather can get quite hot for hiking the hills (start early to avoid the heat and carry extra water)
Sept-Oct: Enjoy striking fall colors, grape harvest season, cooler weather and fewer crowds

Tuscany In Style

Walk Tuscan wine trails through the timeless landscapes of Chianti to Siena, staying in ‘In Style’ accommodation. This very special tour combines walking with opportunities to eat authentic Tuscan cuisine at a Michelin star restaurant, tour a vineyard and of course sample the world-renowned wines, and stay in the outstanding hotels. An intoxicating mix of exceptional experiences.