A Magical Week of Cycling in Tuscany

Join Italiaoutdoors Food and Wine on our distinctive bike and wine tour of the Tuscan countryside. Spend your day cycling through picturesque vineyards and serene olive orchards, stopping to explore ancient hilltop villages. Take a moment to immerse yourself in medieval and Renaissance history before enjoying a snack of bruschetta and a taste of Brunello with the locals. Each evening, our private wine tastings will introduce you to the amazing regional nature of Italian wines, as we explore the famous wines of Chianti, as well as lesser known regions such as Brunello di Montalcino, Vino Nobile di Montepulciano, and Vernaccia di San Gimignano, along with world-renowned Super Tuscans and Vin Santo.

montepulciano cycling tour tuscany
Montepulciano, Italy


Every Italiaoutdoors Food and Wine tour is designed and led by owners and expert guides Vernon McClure and Kathy Bechtel. Our small group size (4-8) allows us unparalleled access to small family producers, the opportunity to join the locals at their favorite neighborhood trattoria, or dine at that exclusive ten table ristorante. Together with the personalized attention of our owner/guides Kathy and Vernon, our tours deliver the ideal combination of guided activities with the freedom to relax, enjoy, and experience the spontaneous. We hope you can join us on this unique and intimate Tuscan journey as we explore one of the most beautiful regions in Italy ‘as a local’.

To begin your adventure, This email address is being protected from spambots. You need JavaScript enabled to view it., so we can provide more detail, learn about your travel style, your cycling, and help with your pre- and post-tour travel.

7 days/6 nights, Tour Cost: $4395 USD ppdo*

2018 Dates: May 6 - 12, 2018. Guaranteed Departure, only 4 spots left.

October 6 - 13, 2018. SOLD OUT.

This email address is being protected from spambots. You need JavaScript enabled to view it. to request your preferred 2018 dates.


Includes: 6 nights accommodations in 3 star or better hotels, all ground transportation, 5 full days of cycling, guide services, all breakfasts, 3 dinners with wine, daily wine tastings.

We're welcoming single travelers on our tours with one of the lowest single supplements in the industry - only $300!

Limited to 8 participants, for a highly personalized experience and the best access to small local producers.

Click here to learn more about how we design our tours for all levels of cyclists.

Have a small group of 4 or more? This trip can be run as a private trip for your group, for the same price. We can customize the rides for the skill and fitness level of your group, from expert climbers to casual tourist riders.


custom tours italy


Highlights of our Tuscany adventure:


  • tuscany-abbey-view-private-cycling-tourCycling through the scenic countryside of Tuscany, surrounded by vineyards and olive orchards
  • Visiting a family estate to taste their wines and olive oils
  • Stopping to refuel as the locals do, at a small cafe
  • Daily wine tastings as we immerse ourselves in the history and flavors of the Tuscan wine scene
  • The wine towns of Montepulciano and Montalcino, where we can sample wine at the local enoteca, and salumi at the famed town butcher
  • Dining on our favorite Tuscan dishes: bistecca alla fiorentina with steaks from the local Chianina cattle, homemade pici pasta, many flavors of Pecorino cheeses, and the local salumi, spiced with fennel.

Our tour includes:

  • siena italy bike tour
    Limited to 8 participants maximum
  • 6 nights accommodations at 3+ star hotels
  • All ground transfers
  • All breakfasts, snacks on the road as we bike, 4 dinners; the dinners include local wines
  • Wine tastings
  • Bike rental, equipped with water bottle, bag, and GPS
  • Support along bike route
  • All tips, gratuities, and local taxes
  • Any entry fees to museums, villas, other venues we may visit
  • Services of two guides throughout the trip
  • Single supplement of $600 - reduced to $300, a 50% savings!

To receive a detailed itinerary, ask any question, or to sign up, This email address is being protected from spambots. You need JavaScript enabled to view it.. We personally work with each and every guest to make sure our trip is customized to your abilities and preferences. We're also happy just to chat, and hear how you would like to travel.


Learn More: