Experience the best of Tuscany
Luxury Tuscany by Bike
Experience the thrill of cycling through Tuscany's rolling hills, followed by luxurious stays in boutique hotels and charming villas. #Lovevelo #LoveCycling #Ridefurther
Cycling Holidays in Tuscany
What to Expect on This Trip
- Luxury Cycling in Tuscany. Experience the perfect blend of world-class cycling and indulgent luxury, surrounded by Tuscany’s breathtaking landscapes.
- Stay in Style. Unwind in boutique hotels, historic villas, and luxury agriturismos, offering premium comfort and authentic Tuscan charm.
- Ride Through Rolling Hills. Cycle along Tuscany’s iconic rolling hills, with smooth roads leading to picturesque villages and vineyards.
- Exclusive Wine and Dine. Enjoy private wine tastings and gourmet meals, featuring Tuscany’s finest produce and culinary traditions.
- Tailored Experiences. Customize your routes and services, with private guides, support vehicles, and premium bike rentals ensuring an unforgettable journey.
This is a trip based in a single location
You will stay in curated, hand picked luxury accommodation throughout Chianti and the Val d'Orcia.
From full carbon with disc brakes and DI2s to e-bikes and hybrid flatbar bikes, let us know what bike you want in Tuscany.
You have the flexibility to arrive and depart at any time. Just let us know the details and we will do the rest.
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
A Typical Itinerary
Day 1
Arrive into Pisa or Florence airport and you will be picked up and taken to your hotel in Florence. Spend the afternoon exploring the capital of Tuscany and take an evening stroll on the Ponte Vecchio.
Day 2
Today is a chance to immerse yourself in Florence and discover Renaissance art, spectacular architecture and the best gelato in the city. 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
60km total distance
Leave your bags at the hotel for collection and begin your ride out of Florence and into the lush Chianti countryside. You will gently climb out of Florence towards San Casciano before another couple of larger hills stand in your way of some lovely gentle downhill through Certaldo. Stop along the route in the quiet Tuscan countryside to enjoy a coffee and relax in your surroundings. To blend in, remember cappuccino is a morning drink in Italy and not to be drunk after lunch!
The rest of your journey is uphill but it is worth the effort as you arrive at your hotel. The grounds are stunning, the pool beautiful and the vista is endless.
Day 4
56km total distance
There's no need to pack your bags today as you will be returning to the same hotel this evening. Today is one of our favourite Tuscan routes. The morning will see you spend most of your time on downhill sections for about 20km. Then it's a climb to San Gimignano, a sight for any seasoned traveller, and a UNESCO World Heritage Site. Encircled by its medieval walls and with it's 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.
From there, the route heads back out into the countryside finishing with a bit of climbing back up to the hotel.
The medieval San Giminano skyscrapers are a must seeDay 5
60km total distance
You can leave your bags at the hotel as you will be returning there at the end of the day. Today's route is a beautiful 60km loop taking in some climbing and some downhills through this undulating and hilly countryside.
Day 6
70km total distance
Pack up your bags today and they will be collected from the hotel. Today's ride takes us down through the countryside and into Siena, a UNESCO World Heritage Site. The Piazza del Campo is the highlight with it's open square featuring the Mangia Tower.
Day 7
Today is a day to rest your legs after a few days on the bike. You are in one of the finest hotels that Tuscany can offer so relax and unwind.
Make An Enquiry
We are the cycling holiday experts.
Whether you're a keen road cyclist, enjoy riding an e-bike or hybrid bike, or want to get your family more active, we have the perfect cycling holiday for you.
What our Cyclists Say
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
Tuscany Perfection. Oli did an awesome job organizing our trip. I needed his help to pull together a custom trip early and he did everything. Our guide Francesco was incredible. He was a pleasure to ride with and planned routes that were beautiful but challenging. We can’t wait to plan another trip.
Read full reviewSarah
Our trip booked through Love Velo far exceeded our expectations. Our trip was three days in Italy and we rode from Florence to Siena. Picking up the bikes in Florence could not have been easier. All of the accommodations were excellent and the baggage transfers went off without a hitch. I would definitely use Love Velo again and wouldn't hesitate to recommend it to others.
Read full reviewSV
Tuscany through your lens
Join Us on A Tuscany Bike Tour
Why us
Why book with Love Velo?
ABTOT protected
Many of our holidays are protected by ABTOT and you can find our bond using membership number 5523.
Trust
Rated 5* on Trustpilot, 10,000+ Cyclists Travel with Us Yearly.
Exclusive Perks
Free Access to Rewards and Discounts on Top Brands like Garmin, Le Col and Oakley.
Easy Payment
Spread Your Tour Cost Interest-Free.
Other Holidays You Might Enjoy
You may also like these trips
FAQs
Tuscany Cycling Holiday FAQs
