Tuscany Bicycle Tours

Pedal the romantic hills of central Italy.

A Step Above the Typical Self-Guided 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 food!  Even the most low-key restaurants have amazing, delectable food.


Tuscany Bike Tours on Your Terms!

You name the dates, riding distance, and other details of your tour. You have worry-free routing by GPS, and a guide/concierge always available to help you when you need it.

Private Bike Tours

Our private, custom bike tours provide highly personalized experiences.

Fit Your Needs

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.

Inclusions

Included in your tour are all luggage transfers, jerseys, GPS guidance, and much more.

Bicycle Rentals

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

Learn More

Want more info? Click here to learn more.

Review Standard Itineraries

Browse our most popular itineraries, visiting the most desirable sites in the region.

Request Custom Tour Proposal

If you prefer to have a special tour a different from our standard itineraries, request a custom tour.

Our Tuscany Tours

Your journey begins in Florence.

Pedal through well-known areas and towns within the region: Chianti, San Gimignano, and Siena.  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 Tuscany bike tours, we offer something for everyone—from relaxed options that can be completed on e-bikes or hybrid bikes, to 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.

Learn More About Our Tours:

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!
  • The use of a Garmin Touring GPS unit during the tour for worry-free routing. The unit comes with your daily routes pre-loaded. We also include comprehensive routing instructions, including cue sheets with maps.
  • 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.

Are GPS units provided?

Included in your tour fee in Asheville, Tuscany & Provence is the use of one of our Garmin Edge Touring GPS units for the duration of your tour. These easy to use GPS units provide an excellent worry-free routing method that you can depend on throughout your tour. When you arrive the daily routes will be preloaded, and ready for you to use each day of your tour. All you have to do is start the daily route at the beginning of your riding day, and follow the highlighted line!

At the beginning of your tour, your local guide will show you how to use the unit. Additionally, we provide instructions that you can reference when needed. As a backup and supplement to the GPS, we provide a local map as well as routing instructions.

For all other destinations, we GPS provide rental options.

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 OUR GUESTS SAY

“We thoroughly enjoyed every aspect of this tour – well thought out bike routes, very good hotel accommodations (nice, clean rooms and substantial breakfasts), and excellent choice of breweries and brewery restaurants (including brewery tours when available). It was obvious that a great deal of attention to detail had been given to this tour and customer service and client satisfaction was of ut… Read more

Florence

Siena

Panzano

San Gimignano

Montalcino

Montepulciano

Cortona

Volterra

Radda

Greve

Bicycle Tours
Bicycle Tours
Outfitter Bicycle Tours,Sesto Fiorentino,Tuscany-50019,
Telephone No.1.877.275.9241
Tuscany, Italy
Self-Guided Bike Tours & Guided Bike Tours in Tuscany, Italy.

Let us Start Curating Your Cycling Vacation!

Contact Us

USA & Canada: +1-877-275-9241

International: +1-415-322-0421

Email: info@outfittertours.com

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