Our US office is closed Nov 14-15 for a company event—response times may be delayed. On-trip support is available as usual!

 

Classic Chianti: Florence to Siena

From $1,665.00
8 Days & 7 Nights
4.6
Read 30 reviews

Classic Chianti: Florence to Siena

  • Experience Tuscany’s Chianti at your own pace with a mix of hiking & time at leisure
  • Explore the two great medieval cities of Florence & Siena
  • Surround yourself with timeless landscapes of vineyards, olive groves & cypress trees
  • Sample the premium, world-class wines of the region, such as Montalbano
  • Hike into the glorious medieval city of Siena, a Gothic open-air museum
  • Stay in hand-picked accommodations all in enchanting locations
Discover the magic of Tuscany on this wonderful hiking tour. Begin with beguiling Florence, the Cradle of the Renaissance, visit medieval Siena, a UNESCO World Heritage Site and enjoy sublime hiking throughout in the Chianti region. Wander through beloved Tuscan landscapes and an intoxicating mix of serene scenery; quiet forests, pretty wooded valleys, row upon row of vineyards and iconic cypress trees, small hamlets and old farmhouses. This unforgettable getaway under the Tuscan sun has a plethora of highlights. Take a walking tour of Florence, a city of timeless beauty. See Michelangelo's David in the Uffizi and the stunning Duomo. At the end of your walking day sample the world-famous and full-bodied Chianti wines and spend your overnights in hand-picked accommodations all in glorious locations.

Itinerary

Day 1 Arrive Florence and overnight Day 2 Walking tour of Florence (self-guided); free afternoon 6 miles / 10 km Day 3 Private transfer to Radda in Chianti; loop hike via Castelvecchi & Volpaia Vineyards 8 miles / 13 km Day 4 Hike to Gaiole in Chianti via Vertine 9 miles / 14 km Day 5 Gaiole in Chianti loop hike via Badia a Coltibuono Monastery & Riecine Winery 9 miles / 15 km Day 6 Hike from Gaiole to Lecchi in Chianti 6 miles / 10 km Day 7 Transfer to Pievasciata or San Sano; hike to Siena 10 miles / 15 km Day 8 Onward travel from Siena
THIS TRIP'S CARBON SCORE

This trip has a carbon score of 4kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 4kg is equivalent to 2.5 avocados. Here at Macs, we pride ourselves on being a responsible travel company and continue to adopt, develop and innovate ways to positively impact the environment. Find out more information about how we've carbon counted our trips.

Reviews

Other Information

Is it for me? Accommodation & Meals Navigation What's Included When to go Travel & Transfers Info & FAQ
Featured
You May Also Like
  • 7 Days 6 Nights

    Tuscany In Style

    Hike Tuscan wine trails through timeless landscapes, staying in premium accommodation.
    Highlights
    • Stay in exceptional hotels & hike in Chianti
    • Enjoy wine tasting and a Michelin star dinner
    • Explore Siena, a UNESCO World Heritage Site
    From $3,715.00
    Activity
    Level
    Accommodations
    Level
  • Slower Adventures
    Type Slower Adventures
    10 Days 9 Nights

    Trails of Tuscany & Umbria

    Hike from medieval and Renaissance hilltop town of Tuscany and to Umbria, the green heart of Italy
    Highlights
    • Spend 10 inspiring days hiking Tuscany & Umbria
    • Explore renaissance Florence & Siena - UNESCO site
    • Trails through vineyards and olive groves
    From $2,240.00
    Activity
    Level
    Accommodations
    Level
  • Slower Adventures
    Type Slower Adventures
    8 Days 7 Nights

    Hiking in Umbria

    Hike through Umbria, the green heart of Italy, from Spoleto to Assisi.
    Highlights
    • Delve into Umbria's cultural and historic roots
    • Remarkable hilltop towns of Montefalco and Spell
    • An unspoiled region of old-world traditions
    From $1,800.00
    Activity
    Level
    Accommodations
    Level
  • Slower Adventures
    Type Slower Adventures
    7 Days 6 Nights

    Cycle Sicily's South

    Discover the UNESCO listed Baroque towns and charming fishing villages of south east Sicily.
    Highlights
    • Ride from the Mediterranean to the Ionian Sea
    • Discover the Baroque cities of Syracuse and Modica
    • Indulge in local cuisine; seafood is the specialty
    From $1,415.00
    Activity
    Level
    Accommodations
    Level

Why Macs

Reasons to believe in Macs Adventure:
The Biggest Choice

The Biggest Choice

Self-guided hiking & biking is all we do - we have hundreds of tried & tested trips.
Our Heritage

Founded in 2003

We’re still founder led & the world’s number one self-guided operator with mountains of experience.
Reviews

23,000+ Customer Reviews

Plus, with a Feefo Platinum Service Award & British Travel Awards, you know you're in good hands.
Positive Impact

B Corp Certified

We’re proud to be B Corp certified, reflecting our commitment to sustainable travel that supports communities and upholds the highest social and environmental standards.
Currency:
$ - USD - US Dollar
Country/Region name:
USAUSA