Tour Details

  • Monday, September 25th to Tuesday, October 3, 2017
  • Three pigger riding—plenty of challenging riding and one 90-mile transfer day, some dirt riding required
  • $4,050 per person; $500 extra for a single room (Single rooms are limited)
  • Eight days of glorious riding, food, wine and transportation—all included. One lunch and dinner on your own.
  • We pick you up at the Pisa airport (PSA) Monday, Sept. 25 at 11 a.m. and drop you off Tuesday,Oct. 3 at the Florence or Pisa airport or the local train station–flights on Oct.3 must be scheduled after 10:00 a.m.
  • Bike rentals available
  • Vegetarian? Food restrictions? No problem!
  • September is harvest time—wine and fruit—so bring an appetite.
  • L’Eroica Bike Rally will be happening on this tour, read below for details!

Castagneto to Chianti

We’ll split the week in two amazing places in Tuscany—the tranquil coastline of Castagneto Carducci and the vine-coverd interior of Chianti. The roads are secluded and winding through vine-lined hills, chestnut forests and picturesque villages. We’ll enjoy the late summer weather on our bikes while indulging in the local food and wine.

For those of you looking for longer days in the saddle while still having time to soak in the culture of bella Toscana, this tour is for you!

Book it now!

All the particulars

Weather: Expect mid-60s to mid-70s, maybe 80s if summer is being stubborn. It will be Fall and cooler so bring a riding rain jacket (waterproof!) and a sweater for the evenings.

Riding level: This is a 3-pig tour. Fit, enthusiastic cyclists will love the riding. Be prepared for hills, and lots of ‘em–central Italy has very little flat or boring real estate! We can vary the mileage greatly on this itinerary, so if there’s a motivated group of riders, we’ll add some loops for them.

Mileage/Terrain: Typically we pedal 350 miles, on this tour–and much of it on the hills. Yes, central Italy and our little corner of Tuscany for this week are quite hilly. Daily rides will range from 35-70 miles with one 90-mile transfer day. There’s plenty of rolling, moderate terrain, too. The first half of the week we’ll be along the Etruscan coast, so plan on a flat-ish ride to the beach one day, then back into the rolling hills. The winding roads of Chianti cover some of the most tranquil and idyllic scenery in all of Italy. We like to get off the beaten track on the celebrated strade bianche, we’re talking dirt roads here people. Mount fatter tires–25 to 28mm–for comfy riding on the dirt sections.

Full disclaimer… the “driveway” to our hotel in Chianti is 500 meters of dirt road with a 4k dirt shortcut to avoid a busier paved route.  Most of our rides will start/finish with these dirt roads. We encourage our guests to try riding this strada bianca at a mellow pace. If you cannot wrap your head around dirt riding you’ll just start the first/last 4k of the ride in the van. We’ve had great success with dirt riding on this part of the tour–it’s worth a try!

The world-famous Eroica Bike Rally runs in this area of Chianti. The intrepid among us can ride some of the dirt sections of the course during our week, or participate in the event on Sunday, October 1!  (see below for details)

We love the dirt roads as they offer a special, historic perspective of Chianti. With that being said, every cyclist must ride within his/her limits. We’ll suggest dirt options along the way but it is never required. Alternative paved routes will not always be available, so if we’re covering dirt portions you don’t want to ride a cameo in the follow van will be your option.

Whom is this trip best suited to?  Cyclists, foodies, and wine geeks…like us. We’ll be tasting the local wine DOC stars: Chianti, Brunello, Montecucco, Bolgheri and Val di Cornia. Sound good? It’s why we keep going back! If you’ve kept your riding steady throughout the summer months you’ll be happily fit for the terrain.

As a non-rider, what else is there for me to do in the area? We do not have a separate itinerary for our non-cycling guests. We stay in tranquil, secluded spots and will visit some charming hill towns. Many guests arrive a few days early to soak in just a sliver of Florentine history, art, and architecture. Both hotels have marvelous pools to lounge by and are surrounded by roads to walk/run on. There is plenty of relaxing to be had for the mellow, non-cyclist and a cooking class to take part in. For those looking to be more adventurous they might consider renting a car to allow for more flexibility in sightseeing… or, hop in the follow van and join the ride as we pass through the many sweet villages of Tuscany!

What bike/gears/tires should I bring? Your favorite road bike will love Tuscany. In general, when heading towards the mythic rides of Chianti, we ride larger tires and maybe slightly easier (shorter, like a 13×27 in the rear) gears for the climbs. Compact cranks are the way to go for this trip too. Chianti offers fine dirt road riding, and more rubber means more comfort and stickier adhesion–some of us even ride 33mm tires! They’re great on the descents and soften bumpy dirt.  Don’t be intimidated; all of the dirt is at a relaxed pace. Bring your trusty steed, with perhaps a slightly wider tire (25-28mm) if you’re interested in opting for more gravel roads.

Bike Rentals: Rentals are available for this tour. Rentals cost 250€ for the week. If you’re interested in a rental check out our Rentals section on the Travel Help page or email

Single Rooms: single rooms are limited on this tour and will be allocated on a first come basis. Please request a single room on your booking form if you are interested and we will do out best to accommodate you.

Where do we go?

Guilty as charged–we love to ride great roads, eat and drink like royalty, and put the legs up once in a while, too. This week features two of our favorite corners of the world, and they happen to be a beautiful day’s bike ride apart.

The first four days of our trip is based at our home town of Castagneto Carducci. Situated along the Mediterranean coast and in the Bolgheri wine DOC, our first hotel is family-run with deep cycling routes and a keen knowledge of how to keep us well fed. Some of the world’s most famous wines are from here, and there are still families making genuine wines too. Nice beaches without crowds are a short ride away. We are lucky to call it home. These days will include rides winding through chestnut forests, olive groves and vines.

From Castagneto Carducci we will ride through the Metallifere hills towards Siena and into the glory of Chianti. This will be our long day on the bike (90k) and worth every pedal–the scenery is spectacular and the experience is not to be missed.

Our second hotel is a wonderfully restored farm near the village of San Gusme. Our rooms at this inn are apartments, the renovated living quarters of farmers from centuries ago. Away from traffic, this is the ideal Tuscan experience. Our meals are all home-cooked by the staff of locals, the wine produced within 10k of the farm.

Travel Details:

Schedule your flights in and out of Pisa airport (PSA) or into Pisa and out of Florence (FLR) on Oct. 3. The shuttle on Monday the 25th will be from Pisa airport only at 11:00 a.m.. At the end of the tour we can drop you off at Florence airport after 10:00 a.m. or Pisa Airport after 11:00 a.m.

Cinghiale Shuttle Schedule

Pick-up: Monday, September 25, 11 a.m. at the Pisa airport.

Drop-off: Tuesday, Oct. 3, at the Pisa airport by 11:00 a.m. or Florence airport 10:00 a.m.—early morning flights on Oct 3 are NOT accommodated due to our location in Chianti, please schedule afternoon flights home on the 3rd.


The world-famous Eroica Bike Rally runs in this area of Chianti. We’ve experienced L’Eroica before and it is truly one of our collective best days on the bike, ever. The energy is amazing as cyclists of all ages bring out their ‘old’ bikes, in traditional garb, and head out to ride the strade bianche. Rest stops are traditional with all sorts of delights to fuel the ride.

We’ll soak in as much of the good ole days as we can on September 30th and October 1st, exploring the exposition of L’Eroica on Saturday and the ride itself on Sunday.

If you are interested in riding the actual event of L’Eroica please indicate so on your booking form in the comments field and please visit the Eroica website for specific details and requirements of the ride.

For our guests not interested in participating in the Eroica itself we will have a guided ride that day as well.


Florence: Consider arriving early or staying a couple days longer to experience Florence. A few days will only whet the appetite, but this is the Renaissance city. Art, architecture, history, philosophy–Florence is unparalleled. For you race fans, think about visiting Florence to see the race on Sunday.

Named in the first century BCE, Firenze, “The Florid,” was built by the Romans on the Arno river. With hot springs, a water source, and a strategic location, Florence quickly grew into a favored city. The Romans left behind an amphitheater and gradually Florence, under the eye of the powerful Medici family, grew into the most cosmopolitan city in Europe by the late Middle Ages. Soon after, Donatello, Brunelleschi, Michelangelo, and daVinci jump-started the Renaissance…and the rest is history.

We like reading about Florence in the Eyewitness Guide to Florence and Tuscany, available through Amazon Books or your favorite local bookseller. Irving Stone’s The Agony and the Ecstasy, about Michelangelo painting the Sistine ceiling, is also insightful about Florence during the Renaissance.

If you are interested in a walking guide let us know in an email.

Siena: One of our favorite cities in Italy, Siena is well preserved and romantic, the site of the infamous Palio horse race. Riders from each of the city’s neighborhoods, called contrade, compete for bragging rights until the next event. The city feels much like it did 700 years ago, with high, imposing walls surrounding the center, and a town hall and cathedral filled with important frescoes and art. You may see the work of Pisano, Ghirlandaio, Michelangelo, Ghiberti, and Donatello here. September, too, is the only month of the year in which the town uncovers the legendary mosaics on floor of the cathedral–a rare opportunity!

Trip details

Included in the cost of the tour:

Eight nights and eight days fully supported riding, with guides and hotel accommodations; transportation to airport (PSA) on the first and ninth day (PSA/FLR).

Eight breakfasts, seven lunches, seven dinners (with wine!).

Snacks and drinks on rides, transportation and admission to scheduled sightseeing stops and special events, provided.

Pick-up at the Pisa Airport and drop-off at the Pisa airport (PSA) or Florence airport (FLR).

Not included with the tour: Airfare. Tip for guides.

Tour Cost is $4,050 per person.

Single rooms are $500 extra per person. Please request a single room on your booking form if you’re interested.

Deposit $1,000 per person. Please wait for us to respond to your booking form to send in your deposit.

Final payment A balance of $3,050 per person ($3,550 for a single room) is due by June 26, 2017. If you are signing on after this date, just drop us a line and we’ll arrange a different payment schedule.

Confirmation and communication

Once you’ve sent us your booking form, you can expect the following communication and requests from us:

A reservation email–Andy or Elaine will respond, letting you know about availability for the tour. If we have space available, they’ll instruct you to send your deposit of $1,000 per person, by check, to our address (provided in the email).

A deposit email–we’ll acknowledge receipt of your deposit, confirming your spot(s) on the tour, and give you a balance and its due date.

Balance email–once we’ve received your balance payment, we’ll acknowledge its receipt, and remind you to send us your travel details so we can confirm ground transportation/ shuttle times with you.

For cancellations, see below.

Trip files–One month before your trip, we’ll send you an email with five attachments, including an agreement to sign, a medical questionnaire that must be filled out, travel info, contact info for each day of the trip, and a suggested packing list.

Itinerary–Upon arriving in Italy, we’ll provide you with a detailed itinerary and route map.

Travel confirmation—Send your travel plans to us at least one month before the trip (airline, flight number, arrival and departure days and times) to We’d like to know how you’re arriving in Italy, so we can make sure everyone’s covered in getting to the tour on time.

Contact us

If this info hasn’t answered all your questions, then drop us a line via email or by phone:

Andy in the US– (303) 506-1788 or Elaine (303) 888-4543 (US mountain time)

In the spring and fall we are in Italy, so please call: (Central Euro time; please call during daylight hours in Italy.) Andy in Italy (011 39) 333 97 60 997 or Elaine (011 39) 346 68 55 070

Booking Travel

Specific information for your tour is contained in the Travel Details section above, so please read it carefully. Please visit our Travel Help and FAQ’s page to answer questions about booking, travel, and your tour.


If you decide not to come or cannot come for any reason, the amount you have paid is fully refundable up to 91 days before your trip. We do not refund money after 90 days. This means if you cancel within 90 days of your trip, you will forfeit the full amount you’ve paid.

We reserve the right to cancel your reservation with us if we have not received your balance payment by July 5, 2016.

We do not overbook our tours and we strongly recommend travel insurance. Please purchase travel insurance that covers trip cancellations (for any reason), lost luggage, and unforeseen medical emergencies.

Travel insurance:

Visit for an insurance quote and for a travel health insurance quote.

Thanks for your interest and we hope to see you soon!