Luxury Tuscany by Bike

  • Road Cycling
  • Spain
  • 5 Nights
  • 4* Accommodation

Fine wine, finer food and a country that has cycling in its blood. Italy is a fabulous place to visit on 2 wheels whether you’re looking for a relaxing trip with the family to Puglia or to ride through Tuscan landscapes that are so striking they look photoshopped.Come and explore the stunning Chianti countryside. You will visit all the main Chianti towns, explore endless olive groves and vineyards, and see incredible medieval cities such as San Giminano and Siena, UNESCO World Heritage Sites. You will spend the 7 nights in various luxury hotels set in beautiful, picturesque locations all over Tuscany. From the vineyards in Chianti to the boutique residence in Florence, the great accommodation will be a real highlight of the trip.

  • 7 Nights luxury accommodation
  • Bed & Breakfast
  • Routes
  • Airport transfers
  • Dedicated telephone hotline
  • Great bike hire
  • Essential bike repair euipment
  • Daily baggage transfer

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

Explore Florence

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

Cycle into Chianti

Total distance 60km

Total climb 1200m

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

Explore San Giminano

Total distance 56km

Total climb 950m

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.

Day 5

Exploring the South of Chianti

Total distance 60km

Total climb 1000m

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.

You will pass through Radda in Chianti, a beautiful medieval town, perched on a hill with stunning views. From there, it’s on to Castellina in Chianti and some spectacular roads leading to this hidden Chianti landmark. Castellina’s history goes back to the Bronze Age and like Gaiole, it’s neighbour, it’s well known for its deep tasting, spicy and peppery olive oil. You will notice the colour and texture changes in the olive oils you taste as you ride through the region.

Day 6

Cycle to Siena

Total distance 70km

Total climb 1200m

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.

The city will be flying the flags of the local contrade, or city ward and the right to fly the flag is won and lost in an epic biannual horse race known as the Palio di Siena, that has been run since the 14th century. Run on 2 July and 16 August, the Piazza del Campo is turned from a popular square into a horse track featuring bareback riders being thrown from their mounts in ever tightening turns. If you happen to be travelling at this time, this is one of the ultimate Tuscan experiences.

Your hotel tonight is the stunning Castello di Casole. This is a hotel quite unlike any other. Offering stunning views over the countryside from the pool and sat within opulent grounds, this is our favourite luxury hotel in Tuscany.

Day 7

Rest Day

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.

Day 8


Today you will be transferred back to the airport for your return flight home.

  • 7 Nights luxury accommodation
  • Bed & Breakfast
  • Routes
  • Airport transfers
  • Dedicated telephone hotline
  • Great bike hire
  • Essential bike repair euipment
  • Daily baggage transfer

01425 206694

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