Tour Details

  • 9 nights, 8 days of riding through Tuscany’s beautiful Spring terrain
  • 3 pig riding, with a mellow Spring pace—This is a giro-style tour where we will transfer three times to different locations: three 100k transfer days and shorter loop rides throughout Tuscany
  • $4,200 per person, single room supplement varies from $400 or $550
  • Single rooms are limited at some locations and singles will need to share a room for 3 nights during the week .
  • Fly in and out of Florence (FLR), Pisa (PSA), or Rome (FCO) airports for easiest access to the train.
  • Tour starts on May 28th from Chiusi-Chianciano Terme train station with shuttles at 3pm and 5pm.
  • Tour ends on June 6th in Siena with drop offs in town or at the train station, and Florence airport
  • We will officially start the tour over dinner at our inn near Montichiello on Sunday May 28th and begin riding Monday May 29th
  • Schedule your return flight for late June 6th or June 7th

What is so jolly about this trip?

Our Giro trips are made to roam and this journey is designed by our guides to explore the out of the way places we love to visit on our own. Jolly is how Italians call a Joker, and we plan on having as much fun as possible visiting four locations in southern Tuscany.

We have been touring with fun, happy guests since 1998 and love repeating our best trips, but we make sure we are searching for new adventures around Italy as well. We listen carefully to our consiglieri guides, and have had wonderful adventures with our giro-style trips in Basilicata and Sicily—So why not repeat this tactic in Tuscany? We considered all provinces and are pulled to the southern and wilder edges of the region. These locations are known to us from previous exploration, but we have never stayed as long as we would like in any of them.

We’ll go full Cinghiale on this tour and turn over as many new stones as possible. Sangiovese wines, Etruscan Ruins, the heart of Tuscan cuisine—andiamo!

Book it now!

All the particulars:

The end of May should be fine weather, we’re going with 70s with a chance of 80s. Bring a rain jacket, but plan on mild, sunny weather.

Riding Level
This is a three-pigger with plenty of climbing.

The terrain will be mostly rolling hills including three transfer days with vertically challenging routes, one day that finishes at 1,400 meters. Our distances will be kind, and there are a few flat roads to enjoy. We know it’s Springtime and will keep the pace mellow so we can enjoy the surrounding views.

Plan on cycling about 290 miles during the trip, much of it on rolling hills that average about three miles in length. Our ride distances range from 40 kilometers to 100 kilometers on the longest day. Strong riders are encouraged to let us know when they want a little extra, and there is no shame in keeping our follow van driver, Gerardo, company for part of the longer days.

Where do we go? 

We’ve been rediscovering Tuscany and look forward to spending time cycling in different and new-to-us places over this week. Our rides will take us on some of Tuscany’s most spectacularly abandoned roads, our wines will be local and draw from the areas of Montepulciano, Chianti, Montecucco, Val d’Orcia and Montalcino’s Brunello goodness.
Our first inn is a gorgeous 19th century farm manor, very close to Monticchiello in the val d’Orcia, with a kitchen serving organic foods—And wine. Very nice wines with a gorgeous vino nobile di Montepulciano. We’ll spend our first rides looping around the area near Montepulciano and Pienza,.

After three nights there we will ride 90 km to Sovana in the province of Grossetto. Sovana has been inhabited for thousands of years with it’s peak perhaps being the Etruscan culture before Rome came to power. We will spend two nights here and explore the Etruscan archeological remnants nearby. The next stage is on the up-and-up to Monte Amiata, which hosted the Giro d’Italia as a mountain top finish. We have often visited this extinct volcano to enjoy the wooded slopes and our friend’s wonderful hotel. The food here is amazing, and we will have a rest day with options to hike in the woods.

Our ride from the mountain will be a joy for the first hours, and then a struggle up through the vineyards into the Brunello DOC of Castelnuovo del Abate to Montalcino. We will visit our favorite winery nearby to sample wines and enjoy the vineyard over dinner.

Cultural Highlights include: UNESCO Val d’Orcia area, Monticchiello, Sovana, Monte Amiata, Montalcino

As a non-rider, what is there for me to do in the area? It is a wonderfully scenic trip for non riders. We will not have a specific program as an alternative to riding. Many afternoons will have walking trips to sights, and all of our accommodations will be situated in ideal spots. Two hotels are situated in the country, and two in towns.

What Bike/Gears/Tires should I bring? Your favorite road bike will do just fine. Lately we’ve been riding compact cranksets to make the hills a bit more casual, so if you tend to suffer on the up, consider a triple or a compact. We will ride a 1 km gravel driveway at the first hotel to start and end our rides there. The dirt options are littered around us, but most routes are on pavement.

Bike Rentals
There are rentals available for this tour. If you’re interested in a rental please send in a form from our website.

Travel Details

This tour begins at the Chiusi-Chianciano Terme train station.

Use Pisa (PSA), Florence (FLR) and Rome (FCO) as potential airports. From there take a train to our pickup point. We will pick up in the afternoon with two meeting times at 3pm and 5pm on the 28th. We suggest coming in a day early and getting over jet lag. Pisa is a mellow place to get over jetlag. Florence is more stunning and busy. Rome is madness, and a must see, but think of hitting it hard after the tour when you are over the time change.

We will meet at the Chiusi train station at 3:00 or 5:00pm in the afternoon. It is a short drive from there to our inn near Monticchiello. Our goal is to get everyone together and happily fed over dinner. Lets call it a prologue.

The riding fun will start the next morning. Therefore this trip is one day longer than most of our trips.

Cinghiale Shuttle Schedule

Pick up: Saturday, May 28 at 3:00pm and 5:00pm at the Chiusi-Chianciano Terme train station

Pisa to Chuisi train schedule (use Pisa Centrale as the station, and your date of travel).

Florence to Chuisi train schedule (use Firenze S.M.N. as the station,  and your date of travel).

Rome to Chuisi train schedule (use Roma Termini as your station, and your date of travel).

Drop off: Tuesday, June 6th, our shuttle will take guests to Siena, where we encourage you to spend a few days, or take a train from Siena to other parts of Italy and your eventual airport city. By train Florence is closer (1.5 hours), but Rome (3 to 4 hours) has great flights and train connections.

We will also take guests to Florence airport arriving late-morning or mid-day depending on our guests preferences. Please note that we will not get you to the airport in time for morning flights, so schedule flights accordingly. Hint: Don’t hurry home.

Trip Details

Included in the cost of the tour:

Nine nights and eight days fully supported riding, with guides. Transportation on first and the tenth day (June 6)—Pick-up at Chiusi train station, and drop-off in Siena or Florence.

Hotel rooms for nine nights; Nine breakfasts, eight lunches, eight dinners with wine.

Snacks and drinks on rides provided. Transportation and admission to scheduled sightseeing stops and special events included.

Not included with the tour: Airfare. Tips for guides. Bike rental if needed.

Tour cost is $4,200 per person

Single rooms are $400 or $550 extra, per person, depending on availability. Please request a single on your booking form if you’re interested. One of our inns has limited rooms, and we want everyone to enjoy this trip, so we are asking all single guests to share a room for the three nights we will be near Monticchiello, our first hotel. If we have space to accommodate single rooms we will reassess the rooming situation in late March. So please let us know if your participation is dependent on a single room or if you are willing to share a room for the first three nights. We have use of apartments at this inn, so there is a possibility to split the apartments into bedrooms and sleeping on a roll away bed in a living room. The bathroom would need to be shared.

Single rooms in our other towns will be accommodated in one or two structures managed by the same proprietor. Meaning an annex or sister hotel close by. Bummed? Don’t be, it will work out fine. Price if you have your own room the whole time: $550. Price if you have one for six of the nine nights: $400.

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 $3,200 per person ($3,750 [$3,600] for a single room) is due by February 28, 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 where to send your deposit of $1,000 per person.

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 your ground transportation shuttle times with you.

Tour 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, and a suggested packing list.

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

Contact us—If this info hasn’t answered all your questions, then drop us a line via email or by phone:
Elaine in the US (303) 888-4543 or Andy in the US (303) 506-1788 (mountain time) after October 15th.

Andy and Elaine in Italy (Central European time; please call during daylight hours!)
(011 39) 333 97 60 997 or (011 39) 346 685 5070

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. You can of course find someone to buy your place from you.

We reserve the right to cancel your reservation with us if we have not received your balance payment by March 31, 2017.

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!