Great Explorations

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National Geographic

“We found the people we met made the trip so special. Several of us have already been talking about which trip to go on next year.”

– Kay & Jim D,
Burlington, VT

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Guest Travelogue Tuscany

We asked Christin Kyle, a recent traveler with us, to write a short travelogue about her experience in Tuscany. Christin wanted us to create a custom trip for family and friends. Here is what she came back with…

Cycling Through Tuscany

This was a trip to look forward to. I’d managed to convince a group of family and friends to try an active vacation in Europe, and Tuscany was the destination of choice. I asked Great Explorations to create a custom trip for our group of 10; after a great first-time cycling trip in Provence with the company a few years back, I was ready to cycle the hills (and reap the rewards) of Tuscany and wanted to bring friends.

After counting the word ‘hill’ seven times in the Tuscany cycling trip itinerary on the Great Explorations website, I grew a little anxious and called GE to investigate. My dilemma? Though there were a few of us on this trip who might want to crank out the mileage (including my boyfriend who sought a daily work-out), most of the group’s cycle training would be modest at best. With our varied goals and fitness levels, was this trip really going to work?

The GE travel advisor assured me that we’d have daily route options to allow people to ride the pace and the distance they enjoyed. The support van, whose primary role was to move our luggage between hotels, would also be there to provide a lift along the way if necessary. The flexible nature made this trip seem like the right fit and Great Explorations assured we’d have the ‘trip of a lifetime’. We signed up!

We arrived in Tuscany in late October and were rewarded with sunny, warm weather throughout the week. Siena, the quintessential Tuscan town, was our starting point and we were greeted there by Great Explorations owner (and our guide on this trip), Robbin

McKinney. We were fitted with our choice of brand new Cannondale bikes (racing for me and my boyfriend and hybrids for the others) which were finely tuned and ready to ride. Each came with a handlebar bag with map cover so we could easily follow the detailed route instructions and maps.

Day 1 started with a ride north out of Siena…happily downhill! Within a few kilometers we were in the vineyards of Chianti, passing through the rows of sun-ripened vines. Just before lunch, we had our first real hill to climb and some of the group opted to ‘stretch their legs and walk a bit’. We were all rewarded at the top with cold drinks and a Great Explorations lunch with delicious bruschetta appetizers, hearty soups and home-made pastas washed down by some Chianti red. With renewed energy, we continued on (and up) to Radda, and then to our final destination of Castellina, a wine making village in the Chianti region. We checked into the luxurious Palazzo Squarcialupi, and found our luggage waiting in our rooms. Formerly a palace from the 15th century, this distinctive hotel has been lovingly restored with large comfortable rooms, swimming pool and gardens, and a boutique spa. The family who owns the hotel still carries on the wine trade - Chianti Classico is made in the cellar with grapes from the surrounding countryside. Robbin had organized a wine tasting on this first night, where a wine expert gave an introduction to and explained the nuances of Chianti wine. Afterwards, we continued to a nearby restaurant that was filled with locals (always a good sign!) and our table was waiting for us, laden with appetizers of prosciutto, salads and breads. We heartily celebrated our first ride, elated with our achievements of the day.

For Day 2, Robbin described two ride options: a ride to San Gigminano, or one he thought would be more suitable for our group. A few of us chose the latter, taking in an interesting castle in Meleto and the village of Gaiole in Chianti, while others did a different, shorter option, electing to visit Radda and return to Castellina early afternoon for a cooking course in a farmhouse that Great Explorations had rented.

We began Day 3 with a 10km descent to the charming village of Monteriggioni, skirted by medieval ramparts over 500 meters high with 14 four-sided towers. Picture a miniature San Gigmignano, but without the crowds. We lingered over lattes and visited local art galleries. The afternoon ride included a moderate climb but the distance was modest and we arrived in Sovicille and our next hotel, the 200 year old Villa Cennina, a former monastery in the hills south of Siena. Robbin brought in a chef who taught us to make fresh pasta and sauces and then we all sat down in a candlelit dining room to enjoy the meal we helped to cook ourselves!

From Sovicille we began Day 4 by heading further south, across a dramatic region known as the crete. Much of the ride was along a tiny road that wasn’t on any maps, but was beautifully paved and rolling through views we will never forget. Along the way, we stopped to visit an eccentric sculptor who invited us into his castle for a private tour of his art collection. After arriving at Asciano, some of us continued with an optional ride to Monte Oliveto monastery and some took a shuttle there in the van. This side-trip was well worth it as we took a private tour of the famous fresco cycles that were painted by Signorelli and Sonoma in the 15th and 16th centuries. Back in Asciano we checked into the family-run Hotel Le Pace, and later enjoyed dinner at a restaurant in town that had recently opened.

On Day 5, some of the group was interested in the museums in Asciano and the rest of us left early towards Pienza. Robbin had made plans for us all to meet up at a spot just past the

village of Castlemuzio, where a sumptuous surprise picnic was waiting and we lazed away part of the day there.

An afternoon stop included a visit to another monastery - where the English Patient was filmed. In Pienza, we checked into the luxurious Hotel Il Chiostro, with lovely views over the countryside. We were on our own for dinner and followed recommendations from the Travelogue we’d received on arrival in Tuscany. A satisfying end to another dream day in Italy…


Day 6 already?! For our final day of riding our route began on a winding road to Montepulciano, where we were led to an enoteca for olive oil, cheese and wine tasting. After a visit to a local museum we continued on to what was probably our favourite ride of the week, the corkscrew descent to Monticchiello and the incomparable restaurant of Le Porta, where Robbin had reserved us a table on the terrace overlooking a fine slice of Tuscany. Although we could have sat here all afternoon, we knew the last hill climb to Pienza would take some energy so we set off, well-rested and fuelled for the trip. We arrived back early enough to do some shopping, and enjoyed a final dinner in the Il Chiostro dining room.

Reflecting back on this adventure, I can honestly say it was a trip of a lifetime, for the entire group. We’re hooked on ‘active vacations’ and will be back for more…

Christin Kyle, Tuscany, September, 2006