Cycling Chianti & Tuscany

Giro de Tuscany!

Table of contents

Overview

Tuscan Tour Highlights

  • 5.5 days scenic cycling 
  • 300 miles +/-(average 60 miles/day)
  • challenging rides in Chianti  countryside
  • Siena, Montepulicano, Montalcino, Pienza
  • guilt-free enjoyment of hearty Tuscan meals

The Italians will tell you Tuscany is a special place. Indeed, there’s no other region in Italy comparable for sheer beauty, Italian food and friendly people.  Our trip takes in the best of what Tuscany offers avid cyclists.  Starting in the hilly Chianti countryside just north of Siena, we’ll make our way through vineyards, forests and portions of L’Eroica course finishing near the slopes of Monte Amiato and the Brunello wine region.

The Rides. What Tuscany lacks in pitched mountain passes it more than makes up for in demanding rolling terrain. The rides are designed for endurance cyclists who crave short little pitches, twisting fun descents and at least 50-70 miles in the saddle daily. We’ll stop along the way for refueling on Italian espressos, lunch and, of course, the usual goodies in the van. 

The Ride Strong Style.

The tour is designed with an obsessive tendency towards the most well-designed routes, multiple nights in one-of-a-kind hotels, authentic cuisine and, yes, loads of riding. We’ll operate our tour similar to our signature tours with knowledgeable local guides, cycling roughly 50-70 miles/day, eating well and sleeping even better! This is a guided, supported and well-designed trip, however, we can’t push your pedals. To enjoy this tour you should be a cyclist capable of riding the daily distances on undulating terrain. 

Itinerary


Day 1 – Arrival Day.

Your guides will meet you in Siena where we’ll transfer (20 minutes) to our special country retreat. Located in the heart of Chianti, only 15 km from Siena, we’ll spend the next two nights in an authentically restored medieval villa and, now, beautiful hotel. This fantastic property also sits in the center of the best Chianti cycling around. Short spin in the afternoon to test the bikes and loosen up our legs. Welcome reception and our first (of many) memorable Italian dinners. (Distance: 13 miles)

Day 2 – Chianti Classico Loop.

We have a beautiful loop ride of undulating hills through the Chianti countryside past the Castello di Meleto, through Radda in Chianti, Castellina in Chianti and north all along the dramatic Tuscan plateau to San Donato. From here there’s a super quiet (and hilly) secondary road looping south to lunch. It’s mostly downhill hill from here to our hotel (Distance: 55 miles with option to extend another 30 miles)

Day 3 – Chianti to Asciano.

Today is nothing short of spectacular with a postcard perfect route around Sienna in a counterclockwise rotation. We begin with a slight descent into the valley en-route to Castellina Scalo and Monteriggioni. Near Cennia, we turn east for some of the most picturesque riding of the day. Our charming borgo (medieval hamlet) for the next two nights sits high on a hill surrounded by an expansive property (Distance: roughly 75 miles)

Day 4 – Cortona Loop Ride.

We’ll mix things up with the only flat riding in the region through the prosperous agricultural area of Val di Chiana. We’ll start arcing east toward Lake Trasimeno with a welcome effortless spin and long views of Montepulciano. After a café at Castiglone del Lago, we’ll take a quiet to the Strada del Vino and up to the hill-town of Cortona for lunch. (Distance: 70 miles, mostly flat)

Day 5 – Asciano to San Quirico/Montalcino.

The morning brings us more short hills with long valley views before a mandatory espresso stop in Pienza and and a spin past Montepulciano.  Enjoy a long descent off the ridge into the charming UNESCO town of San Quirico d’Orcia before the steady grade into Brunello wine region.  We’ll spend 2 nights in our next hotel enjoying the small cafes, delicious restaurants and warm friendliness of the locals. (Distance: 60 miles)

Day 6 – Montalcino Loop.

Very near our hotel sits Monte Amiato, the highest peak in the region.  We’ll skirt the side and ridge of Monte Amiato (all involving some good concentrated climbing) taking us back to the Orcia Valley where local clubs do their time trial workouts.  Enjoy a final night celebration dinner in town tonight. (Distance: 50 or 70 miles)

Day 7 – Homeward Bound – Arrividerci!.

After breakfast we’ll transfer to the Siena train station for your departures home (or extended vacations in Italy).

Details

Our Classic Tuscany Trip Includes

  • Services of two or more of our smiling, experienced domestiques (i.e. guides) equipped with cell phone;
  • 6 nights accommodation in hotels de charme and small special hotels;
  • Breakfast daily (except arrival day), 3 dinners (including wine);
  • Energy snacks and hydration in the SAG vehichle;
  • Luggage transfer and sag support where possible on the course;
  • Route maps and daily distances; and
  • Ride Strong Travel Planner including information on packing, training and traveling with your bike.

Travel and Bikes

  • You are responsible for travel expenses to and from the arrival and departure city. We’ll send you a travel planner to help with all of the logistics of getting there;
  • You should bring your own bike and helmet (although we’ve been rumored to help arrange bike rentals if you prefer). Contact us during the registration process if you’d like to rent a bike; and
  • Passports are needed for all international tours.

Travel Insurance & Cancellations

Ride Strong Bike Tours strongly recommends purchasing peace of mind travel insurance for unexpected trip cancellations or any necessary medical insurance covering you during international travel. We’ll provide you with information about insurance plans upon receipt of your completed registration form and deposit. Please also see our Terms and Cancellation Policy. Ride Strong Bike Tours reserves the right to make modifications to hotels, dates, routes or tour pending confirmation of our hotels and registrations. We will notify you of any material modifications at our earliest possible convenience. Ride Strong Bike Tours also reserves the right to cancel a tour in the unlikely event of insufficient registrations, inclement weather, wars or other matters outside of our control.

Book this Tour

Book this Tour Now!

Registering for a Ride Strong bike tour is simple and secure. To make a booking for one of our cycling tours, please complete our online registration form. Your booking will be confirmed by email. Alternatively, you can go to our printer-friendly online registration form, print off the page and fax it to us. For any questions with your registration, please contact us at info@ridestrongbiketours.com. A single registration form may be used for up to four riders paying together with one credit card and with the same mailing address.

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Deposit and Payment

To reserve your cycling vacation, we require a deposit of $700 per person on our non-race tours and $1,000/person on Tour de France, Giro d’Italia or other special tours). Your final payment is due 90 days prior to your tour departure. If your trip departs in less than 90 days, full payment is due with your registration.

Your deposit and final payment can be made by check or a major credit card. Checks should be made payable to Ride Strong Bike Tours, LLC and mailed to Ride Strong Bike Tours, P.O. Box 82, Solana Beach, CA 92075. A 3.5% processing fee will be added to all payments made by credit card. We use PayPal for processing secure online credit card transactions. An invoice for your credit card payment + transaction fee will be delivered to you via email with a link allowing you to make online payment using the PayPal services.

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Travel Insurance

You are urged to take out the necessary travel insurance to guard against trip cancellation, delay, medical emergencies or illness. We’ll provide you with travel insurance information after receipt of your deposit and completed registration form.

Please Note

Even after your registration has been confirmed by return email, Ride Strong Bike Tours reserves the right to alter or cancel the published itineraries for whatever reason including, but not limited to, weather or road conditions, accommodation availability or low enrollment. Please see our Terms and Cancellation Policy for details.

 

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