I had 6 days off between tours in Tuscany at the beginning of October last year and was itching for one last adventure before heading back to Boston for the winter.  I’d narrowed my choices down to two epic bike trips: riding from Tuscany to Prague or cycling around Sicily.  It was the cold, wet weather forecast in the Alps that decided things for me.  I wasn’t about to brave the Brenner Pass in an October rainstorm.  So, instead, I decided to head south to sunny Sicily, where summer was still in full swing.

I arrived in Palermo only after a nervous night of train travel.

It turns out bikes aren’t allowed on night trains, but I managed to smuggle mine aboard anyways, disassembling it and wrapping it in a fleece jacket and raincoat so it lost all identifiable features.  Needless to say, it was a relief to get off the train and set off on two wheels.

While I was not necessarily “on assignment for DuVine”, it was hard to turn off my guide sensibilities entirely and not see all of Italy for its tour potential.  Consequently, my impressions of Palermo were largely negative.  Like many Southern Italian cities, it’s a place that you either love or could do without.  It is an aging beauty to whom age has not been terribly kind.  Allied bombing in WWII hasn’t helped, but evening the historic buildings that did survive are often uncared for, covered in the black soot from a century of motorists.  The fact that many of these buildings come from the Baroque period only further emphasizes the sense of decay as the pigeons and graffiti seems to mock the original exuberance and pretentiousness of their designers.  The city’s saving grace is its atmosphere, the hustle and bustle of a place where life is lived on the streets.  But would this make up for its other flaws?  I didn’t think so and I set off into the countryside to find a more positive image of the island.

The greeness of the Sicilian countryside

It didn’t take long.  Immediately after climbing out of the city and onto the surrounding plateau, the landscape opens up.  Two things struck me immediately: the greenness of the countryside and the ruggedness of the mountains.  In a way, it was reminiscent of Switzerland where the rural idyll of green pastures and tidy chalets butts up against the untamed bulk of the Alps.  Here too, great spires of rock emerged from the vineyards and fields.  This would be prime country for a trip, I thought.

However, the towns I passed through, such as Corleone (to whom the Godfather owes his name), were uniformly drab, made up of the universally lamented post-war apartment blocks surrounded by poorly zoned grocery stores and gas stations.

When DuVine creates tours in Europe, we look for the perfect marriage between the work of man and the work of nature.  Rides should only cross the most scenic landscapes and pass through the most attractive towns.  Our entire tour-creating team is famous for elaborate routes that ride along a scenic ridge or avoid a stretch of sprawl.  We only have 6 days to make guests fall in love with these regions, so why not seek out the best?  And this area south of Palermo was nice, but I was convinced that there was better.

I rode that day to Agrigento, famous for its still-standing Greek temples.  Again I was disappointed with the work of man.  The temples were fantastic, but the descendants of these early Greek settlers had strayed far from the simple elegance of their ancestors in the creation of the modern-day city.  Did Sicily really lack any truly attractive towns?  I was losing hope.

The moment of truth came the next evening as I was walking around the streets of Ragusa.  Here again, the city seemed devoid of true charm.  Laid out in a grid pattern, with the streets running precipitously downhill, it was certainly not ugly, but neither was it particularly memorable.  On a tip from my effusive hosts at my B and B, I followed Corso Italia downhill looking for something they called Ragusa Ibla.  I was not looking forward to the climb back up and was almost on the verge of turning around, when this view came into sight:

Ragusa Ibla

While the main city of Ragusa is perched on the hillside above the Irminio valley, Ragusa Ibla is a city apart, perched on a smaller hill of its own that rises from the valley.  The division between the two reflects the differing attitudes of the locals after an earthquake wiped out the original city in 1693.  The nobles rebuilt on the old site of Ragusa Ibla, whereas most of the townspeople said “never again” opting for a safer site on the hillside above.  The result of this noble building boom is the aesthetic gem you see in the picture.  In fact, the whole southeast corner of the island experienced a stunning Baroque makeover during this period of rebuilding.   Finally, I had found the Sicily I had been hoping for.

The next day on the bike confirmed my judgment.  Not only did every town have this beautiful Baroque layout, but the landscape was some of the most beautiful I had ever seen.  From steep gorges to open plateaus, every direction brought a new delight for the eyes.  And from a cyclist’s standpoint, the roads couldn’t have been better.  Often I would go 15 minutes without seeing a car, all while navigating through winding descents, bright green pastures and sweet climbs, that lure you on with tantalizing views around each curve.

Incredible cycling roads

Unfortunately, my time was limited and I had to head back to Messina for a train back north.  However, the memories of those two days on a bike stuck with me and when Andy asked me to create a bike trip in Sicily, I knew right where it had to be: Ragusa and surroundings.

So, I’ve spend the winter physically at a desk in Boston, but mentally exploring this corner of the island.  We’ve looked at every luxury hotel in the region, finally settling on 3 that are not only beautiful places to stay, but also offer guests a window into the past, as they are all restored historic buildings.  The food and wine options are staggering, and from dinner at Sicily’s top restaurant to chocolate and cheese tastings, we will have the full flavor of one of Italy’s most highly esteemed regional cuisines.

Fabio, one of DuVine’s newest guides, and himself a Sicilian (albeit from Trapani on the west coast) is already raving about the tour.  He has been out cycling the routes these past few days and reports that it is the best riding he has ever seen (better even than Tuscany).  I’m about to go down and join him, so I’ll see if his claims stand up to my soft spot for Tuscany.

Fabio, our new guide

By the end of the month, we’ll have all the finishing touches worked out and be eagerly awaiting the first tour.  No other company in the world offers a unique and personalized bike trip quite like this in Sicily that focuses on this one region alone.  There are no long van transfers or whirlwind tours, just great biking from place to place, time to explore the UNESCO world heritage towns of Ragusa, Siracusa, Noto and Modica and the opportunity to get a real feel for Sicily.  All of us here at DuVine are expecting great things!

Tanti Auguri,
Tom Coppock
Guide and Italian Manager

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