Tuscany Bicycle Tours | Tuscany Cycling Tours

Pedal the romantic hills of central Italy on one of our Tuscany Bike Tours.

…Why take a Tuscany Bicycle Tour?

Food, Wine, Culture, and Romance in Tuscany…

What else could be on your wish list for a cycling tour? On our Tuscany bike tours, every town has its own rich history and secrets for you and your loved ones to discover.

And the food… oh the Tuscany food! Even the most low-key restaurants have amazing, delectable food.

Bike Tours on Your Terms!

You name the dates, riding distance, and other details of your tour. This is your self-guided bike trip, so you can do it your way, but rest assured – you’ll have worry-free routing by GPS, bike rental with safety equipment and tools, and a guide/concierge always available to help you when you need it.

Cycling Tours: Highlights & Tuscan Must-Dos

Before you book your Tuscany tour… Read about some of our own favorite Tuscan hidden gems in our blog!

Check out all of our posts about Tuscany on our blog page here.


Tuscany Bike Tour Inclusions


Private Bike Tours

Our private, custom bike tours provide highly personalized experiences.


Fit Your Needs

We are fully committed to providing low-hassle customizable tours that are created to fit each guest’s interests, and needs!


We're on Your Schedule

You name the dates and we curate your private tour.

Concierge Level Service

Ride in confidence with the support of a local dedicated concierge/guide.



Included in your tour are all luggage transfers, jerseys, comprehensive routing instructions, and much more. Read more about our bike tour pricing on our Pricing page.


Bicycle Rentals

High-quality rental bikes available – road, hybrid and eBike.


Learn More

Want more info? Click here to learn more. You can also check out our reviews on FacebookGoogle, and Bike Tour Reviews.

Our Tuscany Bike Tours


Your journey begins in Florence

Your first day of riding is fully guided, with a sightseeing ride out of Florence and into Chianti. Then pedal through well-known areas and towns within the region:

Our longer Tuscany bike tours include rides and stays in Montepulciano, Montalcino, and Cortona.


Let us plan your perfectly customized bike tour in Tuscany

As with all of our private, custom bike tours, we offer something for everyone:

  • Relaxed options that can be completed on e-bikes or hybrid bikes
  • Aggressive routes for avid cyclists on road bikes.

Our suggested itineraries range from 4 to 10 nights, or we can custom design a tour for your pace, needs, and interest.

Next Steps

1. Explore your Tuscany bicycle tour itinerary options

2. Complete the below form requesting more information or a custom tour proposal

  • This field is for validation purposes and should be left unchanged.

3. Complete the Registration Form

Click here to complete the Registration Form to secure your Tuscany bike tour.

Common Questions About our Tuscany Bicycle Tour

If this is a "self-guided" tour, why do I have a guide/concierge?

Our local contact is dedicated to ensuring that your holiday goes as smoothly as possible. Think of them as your local friend showing off their home while you’re in town for a visit. They are there from greeting you at the beginning to saying goodbye at the end. OBT concierges take care of curating excursions taking care of mechanical issues & roadside assistance, luggage transfers from hotel to hotel, providing assistance with routing, and much more. They are a phone call away, and there for you.

We deliver this level of service because you’re exploring an area unknown to you, and having a local contact provides great peace of mind. Let us streamline your holiday so that you can focus on having fun! OBT’s level of service is well above the typical self-guided experience.

What is included?

We take care of everything except pedaling the bike….except for eBikes. The eBikes we provide will help you pedal!

  • All hotel accommodations – mostly 3 and 4 stars but ask for custom accommodation requests.
  • An OBT cycling jersey!
  • Comprehensive routing instructions. GPS unit rentals are available.
  • Luggage transfers from hotel to hotel.
  • Meals as explained in the tour itinerary pages. Usually, this means all breakfasts, no lunches, and some dinners.
  • Detailed route notes, maps, and tourist information
  • Your personal guide/concierge

What is not included?:

  • Transportation to start location and from finish locations
  • Bikes, but we have rental bikes available
  • Travel and Health Insurance
  • Admission to site-seeing venues, unless explicitly mentioned as included
Why is a Private tour better?

Our tours are centered around accommodating our guests and the experience they are craving. Not the other way around.

Have you ever been stuck with a group of people you don’t know and may not particularly like? Or have been required to go along with tour plans or excursions that you were not excited about? Have you ever been in a tour group where you feel like you’re being herded along and hurried regardless of what you’d like to do? We’ve been there and don’t like it either. A private tour allows you to travel when you want and with whom you want. Bring your friends, family, partner, or simply yourself. Let us curate an experience for YOU!

We're on your schedule? How?

From when you register for the tour through the duration of your tour, we cater to your timing.

  • YOU get to name the dates of your tour. You don’t have to choose from a calendar of tours that require you to adjust the timing your vacation plans. Want to start on a Wednesday? Sure! Want to be on tour for 5 days rather than the 6 days on our sample itinerary? That is OK with us.
  • When on your tour you are not being pushed to get on the bike at a certain time with a group. You rise, have breakfast, and roll out when you’re ready.
  • Want to spend more time exploring an area on a daily riding route? Sure! Just make sure you get to the hotel in time for dinner.
Are bike rentals available? If so, what kind?

High-quality rental bikes available – road, hybrid and eBike. We will deliver the bikes to you and fit them to you at the beginning of the tour. Your guide/concierge is always available for help if you have a mechanical issue.

How customizable are your tours?

We are very flexible in the destinations we offer tours. Customization options include the number of days/nights on tour, accommodation level (but we DO NOT go under 3-star), new towns/villages within established destinations, and much more. We are open to trying new things in new destinations! Please ask if you’re not seeing what you want!

We have a minimum of 3 or 4 nights on tour, depending on destination.

How are you "a step above the typical self-guided tour"?

The level of service we deliver is beyond the average self-guided tour. You have the freedom of choosing your tour dates and the flexibility to customize your tour itinerary. During your tour, your local guide/concierge is there to help you every step of the way. We require them to have more regular contact with you, our guests, than what you’ll experience with other tour operators. In fact, some of our guides have been known to offer to ride with you on certain tour dates, if you wish.

If you’re looking to experience a polished professional tour, we are your only choice.

How short can a tour be? Do you provide one-day guiding?

We have a minimum of 3 or 4 nights on tour, depending on destination.  We do not provide one-day guiding.

Can I have a guided rather than a self-guided tour?

Yes, for most of our destinations and most of our itineraries we can create a fully guided experience. Note that a guided tour requires extra planning lead-time and additional cost.

Where can I learn more about OBT's Self-Guided tours?

You have two options:

What is the pricing of the tour?

Pricing varies on several factors: Number of days on tour, double or single occupancy of rooming, and level of accommodation. To discover more about pricing click on the itineraries above and find the “Pricing” tab halfway down the page. Each itinerary will have its own pricing structure.




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