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Cycle through South Tuscany’s scenic roads, from Siena’s countryside to Monte Amiata and the Tuscan coast. Discover stunning landscapes, rich culture, and amazing food and wine—ideal for couples or small groups.
Cycle through South Tuscany in Italy with short ascents and descents through scenic roads and paths. Travel from south of Siena, climbing up the Tuscan volcano, Monte Amiata, and ending at the Tuscan coast. What a wonderful way to discover Tuscany’s extraordinary scenery, cultural heritage and incredible food and wine; perfect for a couple or small group of friends.
Highlights:
Briefing and bike testing on arrival day
Mountain bike rental for 6 days (optional upgrades available)
Itineraries are fully customizable. Pricing available upon request, based on two (2) passengers travelling together sharing one room.
Subject to availability at time of booking. Blackout periods apply. Not valid during trade shows, bank holidays and other special events.
International airfare not included. **European city/tourist taxes collected locally unless otherwise indicated.
For full terms and conditions, click here.
Tuscan Cycling Tour: Italy
Photo gallery
Have a sneak peak of what your trip might look like.
Bicycles
Cycling along Tuscan Roads
Views of Maremma
Roads in Maremma
Rural Landscapes of Tuscany
Tuscan Cycling Tour: Italy
Travel itinerary
FLORENCE | VAL D’ORCIA | MONTE AMIATA | MAREMMA
Day 1
Dinner
FLORENCE — PIENZA
Arrival in Florence and transfer to your hotel in Pienza, Tuscany. Positioned high atop a hill with breathtaking panoramic views of the Orcia Valley, this tiny village is a Renaissance treat and known for its unique city planning. Enjoy your afternoon at leisure followed by an evening briefing and bike testing, dinner and overnight.
Day 2
Breakfast / Dinner
LA CRETE SENESI (45km)
After breakfast, depart for your first tour (medium level) which takes you to the Crete Senesi, an area of the Italian region of Tuscany south of Siena. This area is known for its distinctive gray soil known as ‘mattaione’, which offers a beautiful countryside dotted with Tuscan farmhouses, castles and ancient villages. After covering 45km, return to your hotel for dinner.
Day 3
Breakfast / Dinner
NOBILE DI MONTEPULCIANO WINE ROAD (85 km)
After breakfast, check out of the hotel and begin your 85km (difficult level) day with smooth hills en route to Montepulciano, famous for its two excellent wines. Reach Bagno Vignoni and its ancient thermal waters, then climb steep sections to reach Monte Amiata, passing through Castiglioned’Orcia and Seggiano. Opt to take the van or cycle to the hotel for dinner and overnight.
Day 4
Breakfast / Dinner
THE ETRUSCANS (85 km)
After breakfast, begin your 85km, difficult level trek toward Prato della Contessa and Quaranta, passing the old town of Pigelleto. Along plain roads, arrive in Sorano, home of the Orsini Fortress. Visit the Etruscan village of Pitigliano, known for its white wine. Sovana is your next stop where you will visit the old centre and historic sites. Choose to cycle back or take the van to return to the hotel for dinner and overnight.
Day 5
Breakfast / Dinner
BRUNELLO WINE ROAD (60 km)
Enjoy a buffet breakfast. Begin your 60km (medium level) journey by following the downhill roads to Seggiano, watching the landscape slowly change. Reach Monte Amiata Scalo and continue on to Abbey of Sant’Antimo. Take the ‘hard’ way up to Montalcino, then take a secondary road down the rolling hills of Siena; visit the castle and enjoy a tasting of full-bodied dry Brunello wine. Sightsee in the old village and return to the hotel from Sant’Angelo in Colle for dinner.
Day 6
Breakfast / Dinner
VOLCANO OF MONTE AMIATA TO THE HILLS OF MAREMMA (85 km)
After breakfast, pack your luggage and drive to the starting point of today’s route in Paganico, located in the valley of the Ombrone River for an 85km (medium level) ride. Travel through the hills of Maremma between the commune towns of Volterra and Masa Marittima, journey through the wilderness and continue down the cultural highway of Strada del Vino, the wine trail. Dinner and overnight in the heart of the Etruscan coast.
Day 7
Breakfast / Dinner
TUSCAN COAST
After breakfast, customize your Tuscan coast trail with our expert’s suggestions, followed by a day-long guided biking tour. Enjoy dinner at the ‘ZiMartino Restaurant’.
Day 8
Breakfast
TUSCANY — HOME
After breakfast, check-out of the hotel followed by a transfer to the airport for your departure home.
Tuscan Cycling Tour: Italy
FLORENCE | VAL D’ORCIA | MONTE AMIATA | MAREMMA
Package Includes:
Total of 7 nights accommodation at charming Boutique hotels
2 nights in Pienza, Val d’Orcia
3 nights in Castel del Piano, Monte Amiata
2 nights in Castagneto Carducci, Maremma
Briefing and bike testing on arrival day
Mountain bike rental for 6 days (optional upgrades available)
Breakfast and dinner daily at hotels (beverages not included)
Hotel taxes and service charges
Not Included:
Beverages not included with lunches
International or domestic airfare; airport or departure taxes
Gratuities to guides and drivers
Items of a personal nature
Travel insurance
Reciprocity and/or local taxes if applicable
Visas required for entry into the country as necessary. Please discuss this with your travel agent to determine your requirements prior to departure.
Itineraries are fully customizable. Pricing available upon request, based on two (2) passengers travelling together sharing one room.
Subject to availability at time of booking. Blackout periods apply. Not valid during trade shows, bank holidays and other special events.
International airfare not included. **European city/tourist taxes collected locally unless otherwise indicated.
For full terms and conditions, click here.
8 days
On Request
On their recent trip to Italy:
"We did a 28-day holiday in Italy from mid-September to mid-October with Gateways and I just want to let you know that it was a fabulous trip. We did provide input into what we wanted to do and where we wanted to go and then Gateways came up with an itinerary for us. We tweaked the schedule a couple of times, but were very happy with our plan before we left Canada. I wanted to thank you for organizing a trip that didn't have any glitches. Every hotel, transportation or tour that was booked occurred exactly as it should have. We were very happy with our guides, accommodations and train tickets/private rides. We had a great dinner/wine-tasting/creating your own wine outing at a vineyard in Tuscany on our 40th anniversary. We got to walk up the Leaning Tower of Pisa, take a gondola in Venice, float into the Blue Grotto and so much more. Really enjoyed the trip to the lemon farm/pizza-making excursion in the hills outside of Sorrento. And I'm very glad that we had someone picking us up at the train station in Venice and getting us on a private water taxi to get to our hotel and back to the train station because it eliminated the chance of wasting a couple of hours trying to get on the right ferry with all those people getting off the train at one time...this thank you would have come a couple of months ago, [our travel agent] just responded to my original email to give me your name and email."
Mr. & Mrs. C., Alberta
January 29, 2024
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