Tuscany Bike Tour


Tuscany is one of the most iconic places in the world. And for good reasons!


Could it be the Italian’s love of cycling & pasta? Or could it be the exhilarating terrain and spectacular landscapes?


There’s no  better way to explore this magical area than by joining Jemison Cycling on our signature tour of Tuscany, Italy!

About this tour…

Can you see yourself cycling along tranquil roads and winding your way past old stone villas snuggled in the Tuscan hills?


With your bike you’ll ride over rolling hills, vineyard after vineyard.  True of all Tuscan terrain, there are hills to climb, and plenty of views to savor.


We’ll ride into the heart of Chianti, discovering medieval hilltop towns, artisan shops and family run cafes who serve coffee as a form of art .

Dining in Tuscany

Fine Dining on luxury cycling trip

If you have a passion for pasta, this is the trip for you!


Tuscany is known for it’s incredible food and it lives up to it’s reputation night after glorious night. Enjoy some of the ‘locals’ favorite restaurants as well and upscale dining at the best restaurants.


After our rides, you’ll sample Chianti and Super Tuscans wines from local villages.


A perfect combination of riding – food – wine, make this trip special.

 Jemsion Cycling Tour Accommodations for Tuscany

Siena – Villa il Vignale:  Luxurious self-indulgence, is what you’ll feel as you arrive to this 4-star, restored mansion in the heart of Tuscany. The rooms are incredibly spacious and the restaurant serves only fresh, organic ingredients. Post bike enjoy a massage in the wellness center or a swim in the pool.


Radda – Relais Poggiale:  This beautiful, 17th Century hotel is in the heart of Radda & in the center of the best Chianti vineyards. The swimming pool and restaurant are nestled in the vineyards, making this 4-star hotel an experience to remember.


San Gimignano – Relais il San Gimignano:  All the magic of the Tuscan countryside walking distance fron San Gimignano.

DATES to consider

Starting in 2023 Jemison Cycling Tours will be focusing on small private groups.  If you are a leader and have a few friends or family then we want to work with you.  These small private groups can be guided or self-guided. Self guided trips are great and Jemison Cycling Tours can offer the expertise, the routes and the luggage transfer. You will have the choice of riding with a guide or following a route on a GPS device.


*Private trip options*
your dates with 4 or more guests**

tuscany hotel on Jemison Cycling Tour

Physical Requirements




The best riding & quietest roads in Tuscany are in the hills.  Our trips are for “lifestyle” cyclists that love to ride. 40-60 miles per day average.




If your companion rides only a small amount we offer shorter rides. This is a great trip for non-cyclists, as the best of Tuscany can be experienced via tours in Florence, Siena, cooking classes & walks in the vineyards.


We’ve lived in Europe for over 20 years, researching, riding and choosing the best locations for your vacation.


Marty Jemison has ridden over 250,000 miles as a professional cyclist and will share the best riding roads with you.


Our guides are well traveled and have an attention to detail that is unparalleled by another other cycling tour company in the business. We’re focused on giving you a cycling vacation of a lifetime.

Package Inclusions:

European Knowledge – Jemison Cycling is owned & operated by a former Professional cyclist who raced over 900 days throughout Europe
All transfers
Van Support & Luggage Transfers
Ride Food – Drink Mix
One Guide per 4 Guests
All Accommodations
Snacks on the Fly
All Breakfasts
Most Dinners

2-marty leading the pack

Package Exclusions:


Bicycles (Rental Bikes available)
Personal incidentals & Guide Gratuities (our guides work hard for tips)
*Travel Insurance strongly suggested (www.TravelGuard.com)

Learn more about the tour!