Year in Review: Top Bike Rides of 2019

I didn’t originally think I’d be able to find miles of car-free cycling in Southern California. After all, isn’t this a place known for its traffic? I was pleasantly surprised as soon as I turned from Malibu into the Santa Monica Mountains. Not a car in sight for miles!

I could have been riding the rocky coastlines of Corsica or Croatia, but the roadside cacti and beach views were giving off that California vibe. It’s hard to pick a favorite route from this trip, but a nine-mile stretch through Latigo Canyon stands out: it scales the ridges of desert mountains at 5% elevation, and the Pacific is always in your periphery.

I love California for its year-round cycling potential and had a great stay at the Four Seasons Westlake Village—they have the best pool. Whenever I’m in California I’m conscious of eating simple, clean, and light. I never leave Malibu without having seafood, and Onyx at the Four Seasons was excellent.

I’ve seen the popularity of Portugal skyrocket in recent years, which I think is so well-deserved. Still, people haven’t quite caught on to the Douro Valley. It’s a rustic slice of heaven where real life is happening all around you: a local leading his donkey who gives you a sweet smile; a one-man port producer who shows you the stone basins where his friends and family will stomp grapes come fall.

The riding is so amazingly varied: misty forests, cobblestone villages, bike paths, roads beside the Douro River, even a lunarlike stretch outside Ardãos. Personally, my favorite ride is a seven-kilometer descent into Pinhão—you can see forever from the mountaintops, then you wind your way through vineyards and end right on the banks of the Douro.

After a week of hills, I always appreciate a little luxury. Each hotel in Douro blew me away, but the Six Senses Douro Valley offers an acute focus on wine, their grounds are beyond gorgeous, and the breakfast is so good. Their exceptional spa treatments were the perfect way to cap off the trip.

Everyone loves the Greek Islands, but these are the spots that no one’s talking about. This summer, some friends and I cycled across the islands of Kos, Kalymnos, and Nisiros, to name a few. The cycling was challenging, but we were the only ones on the roads (except for some friendly goats and the rustle of palm trees).

There’s nothing like waking up on a yacht, hopping in a dinghy, and meeting my bike on a rugged, crystal-clear shoreline. Seeing the Aegean Sea as you ground down and pedal hard is so motivating—and so is what’s waiting at the end. Each ride descends into a port where grilled fresh fish and octopus was served. I wish we would all try to live more like the Greeks.

This destination has something for everyone, so if you’re not into earning the dramatic views on your bike you can sit back on the yacht and sip rosé under the Mediterranean sun. If you’re looking for a party, you won’t have to wander far—we had a blast celebrating and smashing plates on Symi.

In Gstaad, the challenges are proportionate to the reward; the cycling here is what it means to “work hard, play hard.” Switzerland hits on all cylinders: everything you encounter—from hotel service to road quality—is the top of the top.

The riding follows narrow roads that hug the mountains and unfurl alongside remote alpine cabins, art enclaves, and cow pastures. It isn’t long until we arrive at the epic switchbacks of the famed Jaunpass, which ascends smoothly into the Swiss Alps at 7.5% elevation. Focusing on the landscape of green hills below helps ease the pain.

After some grueling climbs I like a nice reward, and The Alpina is just the ticket. This hotel sits just above the village of Gstaad and features a high-end spa. I also loved the Michelin-starred Japanese restaurant—they fly in ingredients and fish directly from Tokyo. As the 1990 Margaux flows, you really start feeling like all the finer things in life are at your fingertips.

The Veneto region is classic Italy: ancient art, historic sites, unforgettable landscapes, and the best tortelli I’ve had in my life. Seriously, the tortelli we eat on the first night of the tour was like tasting fresh air, and to meet the family hand-rolling the pasta for us was something special.

One of the great benefits of cycling in Verona + Lake Garda is that you can set the pace however you like. It can be as laid-back as riding a path around Lake Garda or a flat route through the countryside, but there’s some serious elevation to be had in the Lessini Mountains too. Every riding level can find their stride here.

Throughout the week, I found myself feeling exceptionally dialed into the local culture—in no small part because of our guides’ knowledge and connections. On Day 2, Antonia welcomed us into her home in Mantua. We made our own balsamic vinegar with her family, just as they have been doing for years.

Nestled in the heel of Italy’s iconic boot, Puglia’s got those aquamarine ocean views that you rarely see outside the Caribbean. Between its hundreds of miles of coastline and centuries-old olive farms, the air you breathe has that fresh, sweet Mediterranean quality. It feels great in your lungs when you’re on the bike.

Of course, I’ve always believed cycling to be the most authentic way to discover a new place. In Puglia, the combination of constant views and DuVine’s connections makes this especially true. We spend Day 2 working our way down the seacoast, and around the 100-kilometer mark you finally reach the lighthouse at land’s end in Santa Maria di Leuca—so epic.

I really love the properties here, and they all have this luxurious quality while remaining so classically Apulian. The Masseria San Domenico is a great example—the masseria is so connected to Puglia’s history and roots, and these farmhouse-style homes have stood on estates for hundreds of years. I’d go back in a heartbeat!

The cycling in Morocco is off the beaten path, and that’s what makes it magical. My dreamy week in Marrakech was headquartered at Kasbah Tamadot in the Atlas Mountains, where we did some unforgettable mountain biking. We rode on gravel into rustic villages and met shepherds and muleteers on the way. It felt like we were the only visitors in a great, remote expanse.

Morocco is undeniably an adventurer’s destination, and I was game to give up my bike for a few days of hiking. On another day, we visited a Berber family at home and shared a lunch of tajines and traditional khobz bread. Meeting them was so enlightening; I was humbled by their openness and outpouring of love.

You can’t visit Marrakech without making a day of the markets. They sell everything from fresh pomegranates and bottles of orange blossom water to live chickens and lanterns. It was absolutely wild and such a feast for the senses!