Adventure Collective
Cycling & Cultural Retreat in Tuscany Vineyards - Florence

Cycling & Cultural Retreat in Tuscany Vineyards

Sienamoderate

Difficulty

moderate

Duration

3–5 hours per day

Fitness Level

Moderately fit riders comfortable with uphill cycling and long days

Overview

Experience Tuscany’s rolling hills by bike while savoring wine tastings and cooking classes at a historic vineyard farmhouse. Discover why this cultural cycling retreat is a standout in outdoor travel.

North Andover, Massachusetts

A Taste of Tuscany

October 18-25, 2025 • Activity Level 2 • Yoga, Cycle, Hike, Culinary

Select participants and date

About This Adventure

Experience the enchanting beauty of Tuscany on this immersive retreat. Explore medieval Siena and vibrant Florence while staying in a charming 15th-century farmhouse surrounded by vineyards. Enjoy cooking classes, wine tastings, daily yoga, and cycling through picturesque landscapes, creating unforgettable memories in this idyllic Italian setting.

The perfect mix of italian culture, history and active adventure

About

During this retreat, we’ll embark on a journey through the lush rolling hill towns of Tuscany, immersing ourselves in the timeless beauty of the region. Our exploration will lead us to the medieval city of Siena and Tuscany’s vibrant capital, Florence. Throughout our stay, we’ll reside in a charming mid-15th-century farmhouse nestled within its own vineyard, just outside the picturesque medieval village of San Gimignano. The enchanting setting of this farmhouse, surrounded by vineyards and overlooking the Tuscan countryside, promises to be an experience you’ll forever cherish.

Package Includes

  • 8 Days/7 nights in a shared or single room
  • 7 Breakfasts, 3 Lunches, 5 Dinners
  • 2 Cooking Classes
  • Wine Tasting & Tour of Property
  • Florence and Siena City Tours
  • Cycling through the Vineyards Tour
  • Yoga daily
  • Unlimited use of pool
  • Entrance fees, porter service
  • English Speaking Private Guides
  • Airport Transfers

Not Included

  • Airfare
  • Meals not mentioned above
  • Additional tours, excursions or other not included in the above itinerary

Adventure Tips

Stay Hydrated on the Hilly Routes

Carry plenty of water, especially on warmer days, as Tuscan hills can be deceptively demanding.

Bring a Comfortable Bike Seat

Smooth but sometimes uneven roads mean comfort is key for enjoying long rides through the countryside.

Reserve Cooking Classes Early

Popular classes fill quickly; book ahead to secure your spot and enjoy hands-on Tuscan cuisine preparation.

Wear Sunscreen and Protective Clothing

Tuscany’s sun can be strong during midday rides; protect skin and eyes to stay comfortable.

Local Insights

Wildlife

  • European hoopoe bird with its distinctive crown feathers
  • Wild boar occasionally spotted in forested vineyards

History

Tuscany’s vineyards trace back to Etruscan civilization, and Siena’s historic center is a UNESCO World Heritage site.

Conservation

The retreat supports sustainable farming practices and encourages low-impact cycling to preserve the landscape.

Select participants and date

Adventure Hotspots in Florence

Frequently Asked Questions

Recommended Gear

Road or Hybrid Bike

Essential

Reliable bike suited for mixed paved and gravel roads typical of Tuscany.

spring specific

Padded Cycling Shorts

Essential

Enhances comfort during extended rides over varied terrain.

Lightweight Rain Jacket

Spring showers are possible; stay dry without overheating.

spring specific

Reusable Water Bottle

Essential

Keeps you hydrated throughout cycling and vineyard tours.