What happens after I enquire?

We will give you a call to discuss your plans so that we can put together a great quotation for you to look at. If you're happy, give us a call and we will make your booking. If you want to make any changes, that's what we are here for!

Are your cycling tours in Tuscany self guided?

Our cycling tours in Tuscany are self-guided, giving you the freedom to explore at your leisure. Armed with our detailed route packs, you can effortlessly navigate the Tuscan hills and the medieval villages.

What's Included on your Tuscany holidays?

Our self guided cycling holidays in Tuscany typically include airport and luggage transfers, the best bike hire, cycling friendly hotels and amazing routes for you to follow.

What are the dates of your Tuscany bike trips?

All of our self guided bike tours in Tuscany are entirely tailor made. You can choose what day you want to travel and what riding you want to do.

How fit do I need to be?

if you're riding in Tuscany you need to be comfortable that you can ride the hills as there's very little flat riding. The gradients are not too difficult other than those immediately outside hilltop towns (!) but you need to have a level of fitness to ride undulating roads and cover the daily distances.

When is the best time to go cycling in Tuscany?

The Spring, between April and June and the autumn, between September & October are the best time to ride in Tuscany. You can't really ride in the height of the summer as temperatures are far too hot.

Where is good to cycle in Tuscany?

We also love the countryside between Siena and Florence for the best riding in Tuscany. We also recommend starting in Florence as it's a beautiful city to get acquainted to Italian life.

Aerial view of a hillside villa with surrounding greenery and pool

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

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From

£1995

Where

Tuscany, Italy

Dates & Duration

Any Dates, Any Duration

How To Book

Make An Enquiry

Get in Touch

0207 157 1519

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

Accommodation

You will stay in curated, hand picked luxury accommodation throughout Chianti and the Val d'Orcia.

Great Bikes

From full carbon with disc brakes and DI2s to e-bikes and hybrid flatbar bikes, let us know what bike you want in Tuscany.

Airport Transfers

You have the flexibility to arrive and depart at any time. Just let us know the details and we will do the rest.

Digital Route Pack

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 you are given a chance to immerse yourself in Florence before you start your ride into the heart of Tuscany. The most important thing to do is find gelato and we know just the place. Marco Ottaviano Il Gelato on Matteo Palmieri is a favourite 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.

Your bike will be delivered today.
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 Certalo. 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 see
Day 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.

Reviews

What our Cyclists Say

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.

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Abby

I booked through Love Velo because the reviews were so good. I wasn't disappointed. Right from my first contact with LV they were easy to talk to and although I dithered (my first cycling trip abroad) they didn't press me. When I eventually confirmed my booking they took care of everything.

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Stephen

Everything about Love Velo has been faultless. From the initial notification of them teaming up with Le Col and to the pricing being unbelievable and then the customer service, top class. James, if all the staff are as attentive to every detail as you are then everyone will be as lucky as I have been. 100% at some point, hopefully in the near future I will be booking again with you guys. Thank you again

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Ian

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Tuscany through your lens