My Top Five Destinations for Cycling and Art

From 2005-2018, I guided and managed bicycle tours all over the world for the luxury tour operator Trek Travel. When I lived on the road, guiding one to two week-long trips back to back for months on end, I rode through achingly beautiful landscapes and saw remarkable architecture ranging from Etruscan ruins in Spain to Medieval and Renaissance cathedrals in Italy and France. I would sneak in some drawing and watercolor whenever I could on the road, but it was in between guiding stints, when I worked from home designing and overseeing a portfolio of trips spanning the globe, that I got to spend more time in the studio working on larger artworks.

While I had the opportunity to ride some of the most iconic cycling routes on the planet, I also had the luck to experience some awe-inspiring landscapes that inspired much of my artwork and continue to this day to serve as fodder for my imagination. Here are in no particular order, my top five favorite places for the best cycling and art. I’ve added some of my paintings for a bit of color. When you look at each painting, see if you can find the elements – colors, shapes and marks – inspired by the landscapes in these places.

This will come as no surprise because Tuscany has been one of the most popular places for cycling and art (and food and drink and … the list goes on) Well it’s for good reason! I first spent time there when I was studying art and Italian for a semester abroad in Florence. As an artist, it was like going to Mecca for me. Years later, when I worked there as a guide, I learned that it was also heaven for cyclists.

Everywhere I’ve been in Tuscany, as soon as you leave a city and get on a small road, the riding is fantastic. I have a special place in my heart for the roads of the Chianti region, specifically around Radda in Chianti and Castellina in Chianti. It’s hilly, but the food, atmosphere and views make it totally worth it. When you have gotten your fill of riding (is that even possible?), spend a few days in Florence for all the art and architecture you can handle. And you don’t even have to step into a museum to see art (although I recommend you do!). Walk around the city to admire open-air sculptures, beautiful architecture or into the Duomo or any other church for that matter. The entire city is a work of art.
Best time to go is in the Spring or Fall because summers are scorching hot.

Possibly my favorite of all places to ride is in the Italian Alps and the Dolomites. These mountains are located in an area that feels both Italian and Austrian. Because the region changed hands over the years, the region has a distinct bicultural feel (imagine the best of both cultures) and just happens to be a mecca for outdoor sports. In the Alps three of my favorite climbs are Stelvio, Gavia and Mortirolo. All three climbs are tough and unrelenting and beautiful and they feature in the most hallowed chapters of the Giro d’Italia. Andy Hampsten’s legendary 1988 Gavia finish alone in a blizzard comes to mind…

In the Dolomites, my favorite ride is the classic Sella Ronda loop, where you climb four major climbs: Passo Sella, Passo Gardena, Passo Campolongo and Passo Pordoi. Along the base of some of the climbs are some quaint villages where you can stop for lunch or coffee – Arabba and Corvara are my favorites.

If you want a metropolitan feel nestled in the mountains, I recommend spending some time in Bolzano. There’s a great network of bike lanes into and out of the city if you’re in the mood for a meandering ride.

Get some world class culture at the start or end of your trip when you fly into and out of Milan or Venice. You’ll need to take a train (or 2) to get to the mountains, but while you’re in either city, you may as well take advantage of the best of the best! I love the duomo in Milan and if you’ve never experienced a gold-encrusted McDonald’s, there’s one in the arcade there.(Is it tacky to include a gold-encrusted fast food chain in this list? Maybe)

As for Venice, you could time your trip during the Biennale and take part in the one of the art world’s biggest events where you can see cutting edge artwork from all over the world.

Best time to ride in the Italian Alps is middle of the summer where you’re less likely to encounter snow in the mountains – although anything is possible there. I have seen snow in July on Stelvio. Summer time isn’t the best time for Milan and Venice – it gets hot and crowded – but we’re going to focus on the cycling since you can enjoy art without necessarily breaking a sweat.

Climb to your heart’s content with iconic Tour de France summits like Alpe D’huez, Galibier, Glandon… I recommend staying right in the village of Alpe D’huez – the only drawback being that you need to make the climb each time you go back to your base… but there are quieter side roads up the climb to switch things up a little.

When you want to enjoy some culture, check out Grenoble, a relatively short drive away. The city is ideally located at the base of the mountains and features The Grenoble Museum of Art with a collection that spans 13th century painting all the way to contemporary artworks. There is also a great scene of galleries showing contemporary art works. A notable one is Galerie Vent des Cimes.

Best time to visit is middle of the summer when the roads are open and not covered in snow! I recommend bringing layers because the weather can be spotty and occasionally even quite cold.

Provence, France

From the Alps, you can actually drive to Provence in a few hours.

If you use Bedouin as a base, you can ride to vineyards and wineries galore, or you can ride the giant of Provence: Ventoux! The mountain is part of the pre-Alps, and it is just as grueling as all the stories you’ve heard. Climb from Bedouin for the classic Tour de France experience. There’s even an official climb start point at the bike shop La Route du Ventoux. While you’re at it, I recommend stopping in at the shop. The guys there are super nice, they do great work, and they are well stocked with both new bikes and rentals. You can descend the mountain on the same road or down the other side to Malaucène to check out this nice little town and refuel with a lunch or coffee stop.

For a more mellow climbing experience, I HIGHLY recommend riding along the Gorges de la Nesques for one of the most satisfying climbing experiences of your life. The average grade is a gentle 2-3% and there is some kind of cycling magic that happens on that climb where you feel like you have wings – and the views are stunning. End the ride in Sault for a relaxed lunch… or if you’re feeling especially motivated, climb from Sault to Ventoux, for the most “gentle” of the 3 ascents on the mountain. And if you’re feeling a little crazy, climb all 3 ascents on Ventoux in a day for the coveted “Cinglés du Mont-Ventoux” claim to fame. The rules are here.

To get your culture on, make the short drive out to Avignon and check out these two museums (and there are plenty others) Collection Lambert Contemporary Art Museum and Musée Calvet, and art and archeology museum.

Best time to visit is spring or fall, and late spring or early fall is best if you want to climb Ventoux though because the weather on that mountain is particularly nasty.

I’ll admit I may be slightly biased because I called this city home for two years, but I think a location in the Southern Hemisphere helps balance things out.

Adelaide and the surrounding hills is known for its excellent riding and is the home of the Tour Down Under.

The CBD (central business district) is flat and cycling is definitely the best and quickest way to get around. Or you can challenge yourself with a ride out to Mount Lofty, where you can climb up any of the sides for a different challenge and a totally different landscape experience. If you’re there in January, you also get to experience the Tour Down Under, where you get great access to professional teams and world class racing right in the city.

As far as art, Adelaide has a great street art scene and as a result, some beautiful murals you can enjoy on a bike ride or a walk in the CBD. And if you happen to be in the city in February or March, I highly recommend experiencing an event at the Fringe festival. Adelaide has the second largest arts festival (after Edinburgh) and whether you’re interested in performing or visual arts, there is something for everyone – and it’s basically a big party for a month!

If you’re primarily riding, I’d recommend going in the spring or fall. Summers here are scorching hot and winters are quite rainy. And remember, it’s in the Southern Hemisphere, so if you’re traveling from anywhere north, seasons are reversed. And if you’re flying from the US or Europe, the jet lag is cruel. (Don’t resist that nap on the day you get there. You’ll be wiped out anyway and your internal clock will be so messed up, just get as much sleep as you can.)

That wraps up my top five places for cycling and art.

What are your most legendary rides? What if you could have a painting of that ride made just for you? Ask me about my Epic Ride series, custom paintings based on your favorite – most epic – rides you’ve done, want to do, or have seen the pros ride.