Tuscany Wine and Gastro Cycling Tour

History, Art, Wine, Gastronomy and enjoyable cycling – Tuscany has it all!

Tour Highlights

  • Cycle through the Orcia Valley, a UNESCO World Heritage Site
  • Explore the cultural cities of Siena and Florence
  • Taste famous Chianti, Brunello, Nobile and Vernaccia wines
  • Cycle through the classic rolling Crete Senesi hills
  • Take a part in an exclusive, private cooking class
  • View the 13 towers of medieval San Gimignano
  • Enjoy famous Tuscan gastronomy

Pedal our favorite Tuscan roads— on our way from breathtaking Val D'orcia to glorious Siena and Florence. Taste local treats like pasta, pecorino cheese, and bruschetta with local olive oil while tasting the finest Brunello, Wine Nobile, and Chianti Classico wines.

From $ 2650
Activity Level Recreational / Active non-riders are welcome
Duration 6 days / 5 nights in luxury 4 star hotels
Start / End Sinalunga / Florence
Daily Mileage 24 - 32 mi
Daily Biking 3-4 hours
Meals All breakfast, 5 gourmet dinners, 5 Lunches, 3 Wine tastings and Cheese tasting

Itinerary Map

Day 1

ARRIVAL TO SINALUNGA Warm up ride 10mi.

Transfer from the La Chiusi train station to the hotel in Sinalunga. Afternoon gathering with guides and the group, bike fitting, warm-up ride, welcome drink and group dinner.
Day 2

VAL D'ORCIA AND PIENZA 22mi. + OPTIONAL 7mi. Show more detail Hide more detail

The ride sets off from the hotel through the sleepy town of Montisi, overlooking the magnificent Crete Senesi. We continue through the olive groves and vineyards, making a stop in the medieval town of Pienzi, the home of Pecorino cheese, where we will enjoy a cheese tasting and lunch. Following this is a descent through the stunning Val'Dorcia Valley, a UNESCO heritage site. We end today's ride in the quaint town of San Quirico d'Orcia, and spend the night in a hotel in the town centre. Enjoy a relaxing afternoon strolling through the streets, or relax with a massage in the hotel spa.
Day 3

MONTALCINO AND BRUNELLO WINE REGION 24 mi. + OPTIONAL 10 mi. Show more detail Hide more detail

The morning begins with a climb towards the town of Castiglione, with its medieval fortress. After the descent, we enter into the famous wine growing region, Brunello di Montalcino, and at its heart, the town of Montalcino. Here we will enjoy lunch and a tasting of the famous wines in the fortress. After lunch, we will descend through the vineyards to our hotel. Tonight's entertainment features cooking classes with our friend August, who is sure to reveal some of his secrets in preparing famous Tuscan dishes.
Day 4

CRETE SENESI AND ASSA VALLEY 20mi. + OPTIONAL 10mi. Show more detail Hide more detail

We ride through the Asso Valley, arriving in the Crete Sensi region, where you will feel as though we have entered into another world that can only be described as “lunar”, with its gently sloping white hills, almost completely colourless. After a picnic with a stunning view, we will arrive at Siena, and head to our gorgeous hotel in the Chianti hills.
Day 5

CHIANTI CLASSICO 24 mi. + OPTIONAL 11 mi. Show more detail Hide more detail

Today's ride runs through the famous Chianti region, past the down of Castellina in Chianti, Radda in Chianti, and past the endless vineyards of the Castignolli hills, where we will enjoy a wine tasting and lunch. This is followed by a descent and climb from Castello di Brolio, and this circular ride ends back at the hotel. Enjoy an afternoon at the pool in the sun, before we depart for Siena for sightseeing and dinner.
Day 6

SAN GIMIGNANO AND FLORENCE 21mi. + OPTIONAL 10mi. Show more detail Hide more detail

The final day of our tour begins from the hotel. We ride through the Chianti region, past the town of Tavarnelle val'di Pesa, ending in the famous medieval town of San Gimignano, where we will enjoy lunch and pay a visit to the Vercnacca wine museum and have a tasting. In the afternoon, transfer to your hotel in Florence and a farewell to your guide, until your next adventure.


Hotel Relas la Chiusa, Montefollonico

Originally an olive mill, la Chiusa’s  rooms have been sympathetically designed and enjoy a beautiful view from the garden of Montepulciano, Monte Amiata and the stunning countryside.

Hotel Il Piccolo Castello, Monteriggioni

Surrounded by 2 hectares of rich parkland, Il Piccolo Castello is a 4-star hotel immersed in the Tuscan countryside, situated only 1 km from the castle walls of Monteriggioni.

Do you know we offer e-bikes on all tours?

What's Included

Come & Go

  • Exceptional customer service and unforgetable experience.
  • Collection from Chiusi train station.
  • Delivery of your luggage to your hotel room each day.
  • Transfer to your hotel in Florence.

On the road

  • Two vans support with free Wi-Fi internet - will carry fruit, snacks and drinks, bike spares, first aid kit, and, if needed, tired cyclists.
  • Two or three tour leaders per departure.
  • Choice of high quality hybrid and road bikes.
  • Water bottle and bike bag.
  • Quality helmets.
  • Unlimited fruit, snacks and drinks during the rides.
  • RideWithGPS mobile application for routes and navigation.

Wine & Dine

  • 5 gourmet dinners with drinks.
  • 5 lunches with drinks.
  • 3 Wine tastings in famous wineries.
  • Pecorino Cheese tasting.

Stay & Sleep

  • Welcome drink.
  • 5 nights accommodation in luxury 4 star hotels.
  • Breakfast for all 5 nights.


  • Entry fees to attractions and historical sites.

What's not included


  • The price does not include flights.


  • The price does not include travel and trip cancellation insurances.


  • Gratuities for your guides are not included in your trip price. Please tip your guides based on their guest care, service and level of professionalism.

Dates & Prices

* You can download our Terms And Conditions here