A Tailored Cycling Trip in Tuscany
Tuscany Short Bike Tour
Chianti's dramatic views unfold with rolling hills, vineyards, olive groves, and cypress-lined Strada Bianchi roads. #LoveVelo #LoveCycling #RideFurther
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Trip Highlights
Bike Tours in Tuscany
- The Tuscan Hills. Explore tree lined rolling hills and sip cappuccino in a Chianti town square.
- The Wine Visit Montepulciano and enjoy a glass of local wine in the medieval hilltop town.
- San Giminano. The medieval skyscraper town is a sight to behold with epic views across the Tuscan countryside.
- Siena. Visit Piazza del Campo which holds the famous 'Palio' horse race, a twice annual local race that has been a feature of Siena since the 15th century.
- Tuscan Life. Step into the heart of Tuscany and be greeted by rolling hills, quaint farmhouses, and the scent of cypress trees.
This is a trip that goes from place to place
You will stay in curated, cycling friendly, boutique hotels.
We have the best bikes in the Algarve including lightweight leisure bikes, e-bikes and road bikes.
We will provide you with airport transfers and luggage transfers to take your belongings from hotel to hotel.
As part of your cycling adventure, we will provide you with our curated set of digital routes. Just download to your Garmin or Wahoo, or navigate from your phone.
Arrive & Depart At Any Time
Your Day by Day Itinerary
Day 1 - Arrival in Florence
Arrive into Florence airport and we will be on hand to take you to your hotel in Florence. Spend the afternoon exploring the capital of Tuscany and take an evening stroll on the Ponte Vecchio. If it’s romance you’re after, there are an abundance of restaurants sitting on the banks of the Ponte Vecchio, where you can wine and dine by the reflecting sunset.
Day 2 - Explore Florence
Today is a chance to immerse yourself in Florence and discover Renaissance art, spectacular architecture, and the best gelato in the city. Marco Ottaviano Il Gelato on Via Matteo Palmieri is the place to go as they use seasonal fruits and not too much sugar. Spend some time visiting Michelangelo's David, wonder in the magnificence of the Duomo and watch life go by in this extraordinary city.
Day 3 - Cycle to Radda in Chianti
50km total distance
Today's route is a beautiful 50km taking in some climbing and some descents through this undulating and hilly countryside. You will make your way to Radda in Chianti, a beautiful medieval town, perched on a hill with stunning views. Deep tasting, spicy and peppery olive oil, is a feature of Chianti and you will notice colour and texture changes as you ride through the region. From there, you will cycle through the Cypress tree lined roads of Greve in Chianti and Panzano until you reach your hotel just outside of Gaiole in Chianti.
Day 4 - Cycle to San Gimignano
57km total distance
Today is one of our favourite Tuscan routes. You will head west through quiet Chianti countryside towards Poggibonsi. Then it's a climb to San Gimignano, a sight for any seasoned traveler, and a UNESCO World Heritage Site. Encircled by its medieval walls and with its hilltop views, 12th century skyscrapers loom over the Piazza della Cisterna. We recommend a plate of Pappardelle, a favourite in Tuscany, in one of the numerous restaurants and cafes in the town. Your overnight stay will be just outside the walls of this famous city.
Day 5 - Cycle to Siena
40km total distance
Today's ride takes you further into the heart of Tuscany on your way to Siena, a UNESCO World Heritage Site. The Piazza del Campo is the highlight with its open square featuring the Mangia Tower. If you happen to be in Siena on 2 July and 16 August, one of the most thrilling Tuscan experiences is Palio di Siena. The horse race has been run since the 14th century and the Piazza del Campo is turned from a square with people milling about, to a horse track featuring bareback riders being thrown from their mounts in ever tightening turns.
Day 6 - Departure
Today we bid you arrivederci and will organise for your transfer back to Florence. Remember all of our trips can be tailored so if you want to spend longer in the stunning Tuscan countryside, we can organise that for you.
We Are Rated Excellent
Read Our Awesome 5* Reviews
This was my first cycling holiday and was a fantastic experience. The great routes through Tuscany and beautiful hotels were well planned and made it an all-round amazing trip!
Read full reviewSK
Awesome customer Service like it used to be. When planning my husband's 50th birthday and knowing very little about cycling I decided to try Love Velo and I can't recommend them, and the service I've received from James Danvers highly enough.
Read full reviewAbby
We recently travelled to Tuscany with Love Velo, I honestly couldn't recommend this company more. The hotels they chose were incredible, everything worked seemlessly e.g. Transfers, and the bike hire was excellent. I have already recommended Love Velo to friends and we look forward to another trip with them.
Read full reviewJodie
Speak to an Expert
We are your Tuscany cycling vacation experts. Speak to one of the team who has in depth local knowledge and let us curate the perfect bike tour in Tuscany for you.
How It Works
Speak To An Expert
When you’re ready to plan your cycling adventure, our experts are here to make it happen. Call us Toll Free on 1-800-557-9119 or make an online inquiry.
We Will Tailor Your Quotation
We will provide you a tailored quotation to include whatever you're looking for on your cycling vacation.
Pay Your Deposit
We take just a small deposit to confirm your trip, with the balance payable 12 weeks prior to travel.
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Tuscany through your lens
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For more information about other exciting cycling experiences we offer, visit our Italy cycling vacations page.
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