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Tuscany

World-famous Tuscany, in central Italy, is known for its rolling hills, historic cities and landscapes that seem straight out of a painting. With Florence as its capital, it's abundant in art, culture, delicious cuisine and timeless hilltop villages – and in Chianti, one of Italy's best-known wine regions.

Walk from Florence to Siena through the vineyards of Chianti, or from Volterra via San Gimignano to Siena on Relaxed Trails of Tuscany. Cycle from Poggibonsi to Siena and on through Montalcino and Pienza to Montepulciano, or walk Tuscany In Style, staying in a 10th-century monastery and dining at a Michelin-star restaurant.

Pilgrims can also follow the Via Francigena through Tuscany on its way to Rome, on foot or by bike.

10 routes

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Routes in Tuscany

  • Italy · Switzerland

    Via Francigena

    • Walking
    • 8–50 days
    • Easy - Moderate to Moderate - Challenging
    from$2,540CAD pp
    View Route
  • Italy

    Hill Towns of Tuscany

    • Walking
    • 8 days
    • Easy - Moderate
    from$3,050CAD pp
    View Route
  • Italy

    Classic Tuscany

    • Walking
    • 5 days
    • Moderate
    from$1,685CAD pp
    View Route
  • Italy

    Classic Chianti

    • Walking
    • 5–8 days
    • Easy - Moderate
    from$2,165CAD pp
    View Route
  • Italy

    Trails of Tuscany & Umbria

    • Walking
    • 10 days
    • Easy - Moderate
    from$3,720CAD pp
    View Route
  • Italy

    Cycling Tuscany: Chianti & Siena

    • Cycling
    • 8 days
    • Moderate
    from$3,115CAD pp
    View Route
  • Italy

    Relaxed Trails of Tuscany

    • Walking
    • 7 days
    • Easy - Moderate
    from$2,325CAD pp
    View Route
  • Italy

    Wine Trails of Umbria By Bike

    • Cycling
    • 8 days
    • Easy - Moderate
    from$3,510CAD pp
    View Route
  • Italy

    Cycling Tuscany: Florence to Montepulciano

    • Cycling
    • 8 days
    • Moderate - Challenging
    from$4,000CAD pp
    View Route
  • Italy

    Biking the Via Francigena: Lucca to Rome

    • Cycling
    • 11 days
    • Moderate
    from$5,035CAD pp
    View Route

Here's why Tuscany is a favorite with self-guided travelers:

  • Hilltop towns among rolling vineyards and farmland, with panoramic views
  • Renaissance Florence, with the Uffizi Gallery, the Pitti Palace and lively piazzas
  • Siena, a UNESCO site famous for the Piazza del Campo and its Duomo
  • Chianti's vineyard-covered hills and renowned wines
  • Gourmet food and wine, from olive oil and pasta to local cheeses

Tuscany like a local

  • When's the best time to visit Tuscany?

    April to June brings mild weather and blooming landscapes, July and August can be hot for hiking the hills (start early and carry extra water), and September to October brings fall colors and the grape harvest. Tuscany is popular year-round, so book as far ahead as you can.

  • What are the must-visit places in Tuscany?

    Florence, Siena, the vineyards of Chianti, hilltop towns like San Gimignano and Montepulciano, and the idyllic landscapes of the Val d'Orcia.

  • What is a Slower Adventure?

    Active days that are generally shorter, with more time to browse towns, sample local wine, visit heritage sites or relax with an afternoon espresso.

  • What is Tuscany In Style?

    Our upgraded walking trip from Chianti to Siena, with outstanding hotels, a vineyard tour and a Michelin-star dinner.

  • Can I ride an e-bike?

    Yes – on our Tuscany biking trips, pedal under your own steam or relax on an e-bike.

  • Where will I stay?

    In hand-picked hotels and guesthouses in historic towns and the Tuscan countryside.

More regions to explore

  • Italian Lakes

    Lake Como villas, Lake Garda shores and the islands of Lake Maggiore.

    View all 3 routes

  • Puglia

    Trulli villages, white towns and the Salento coast in Italy's heel.

    View all 2 routes

  • Sicily

    Wild western coastline, the Egadi Islands and the Baroque towns of the south.

    View all 2 routes

  • Umbria

    Hill towns, Sagrantino vineyards and the footsteps of St Francis.

    View all 3 routes

Know before you go