Aerial view of two people riding bicycles on a winding paved road through vineyards. There are houses, a river, and mountains in the background.

Sports

Best Bike Trips For All

Larry Olmsted

Two people riding bicycles on a winding road through green hills of Tuscany countryside and vineyards.

Unforgettable Travel Memories

One of literature’s greatest travelers, Ernest Hemingway wrote evocative descriptions of exotic landscapes from the green hills of Africa to the vastness of the American West. The Pulitzer Prize winner gave a simple explanation for his vivid geographic recall: “It is by riding a bicycle that you learn the contours of a country best … you have no such accurate remembrance of country you have driven through as you gain by riding a bicycle.”

When you drive, by the time you turn your head to see something that caught your eye, it’s gone. On foot you can take it all in, but you don’t cover much ground. Traveling by bicycle remains a happy medium, the means by which you see a mix of towns and countryside in a single day and make stops with ease, whether it be for Italian gelato or French wine. You exercise enough to feel good about the indulgences, and, with the right outfitter, if it rains or the hill gets too steep, you have refuge in the support van.

George Butterfield, credited with inventing the entire luxury guided cycling trips category in 1966, coined the perfect motto for his company, Butterfield & Robinson: “Slow Down to See the World.”

Cycling vacations have never been more popular nor offerings more plentiful. A pandemic-induced spike in fitness and cycling intersected with the ongoing trend of experiential travel, and the recent advent of motor-assisted e-bikes was fuel on the fire. E-bikes allow less-avid spouses to keep up with their partners, grandparents to join multigenerational trips, and occasional cyclists to tackle big mountain passes. In just the past three years, they have become standard options from every major tour company.

All top-tier tour operators include a cycling guide and on-route van support, use superior lodgings, manage luggage transport, invest in high-quality bike fleets, and arrange special meals and access for city or attraction tours along the way. Most offer both scheduled, small group departures as well as the option of making any trip private for your party. All are expanding destination offerings and reporting record bookings, with something for every taste. Here, a short list of the best.

Two people wearing cycling gear are riding bicycles on a winding road through the countryside of Burgundy, France. There is a church and several homes in the background.

Several cyclists are riding bicycles on a paved road next to a row of buildings, overlooking vineyards in Czech Republic and Austria. There are mountains in the distance.

A person riding a bicycle on a winding paved road on the coast of Chile. There are mountains in the distance.

Challenging, Athletic

Europe

Most full-service bike tours offer multiple daily ride options, but these usually top out in the low 40-mile range. While more than enough for casual riders, this distance is on the low side for avid cyclists. DuVine is the top tour operator with something for every ability, and its DuVine’s Challenge collection (Level 4) includes five Journey trips with roughly twice the daily mileage and elevation of their Level 3 tours, including the classic Tour de France ascents, such as the infamous Alpe d’Huez. The marquee offering is the Italian Coast-to-Coast Journey, across the width of the country, but there are also Journeys across the Alps in France and Switzerland, through Italy’s Dolomites, and across France’s Pyrenees. It’s a lot of time in the saddle, but all are supported in the same white-glove style as DuVine’s easier trips, and the company is renowned for its culinary emphasis, especially wine, with deep-dive tastings and pairings. From $4,600/person; duvine.com

A white plate of tagliatelle pasta with tomato sauce on a wooden table. There is a smaller plate of cherry tomatoes next to it.

Two tour guides holding a Toscana map in front of a white van. There is a woman in the foreground watching them.

Classic, Tried-and-True

Tuscany

Every major bike tour operator has trips to Tuscany, and with good reason—it’s the most popular spot and often the first place cyclists think to go on these kinds of trips. The hill towns, the countryside, the wine region, the food—it’s all amazing, and because cycling is such a popular sport in Italy, drivers are skilled, patient, and friendly. There are several excellent, white-glove companies in this space, but across the board, Butterfield & Robinson is the most luxurious. The company excels at deluxe accommodations, food, route planning, and support, has extremely high-caliber guides, and focuses on special experiences along the way, such as VIP tours of wineries and museums, often not open to the public. B&R’s top choice is Super Tuscan, starting in Florence and staying at Borgo San Felice, a Relais & Châteaux property, and the stunning Rosewood Castiglion del Bosco. butterfield.com

A female chef teaching a woman how to make pasta outdoors. There are glasses of red wine and a pasta machine on the table.

Culinary, Food-Focused

Italy and the United States

Racers eat to ride, but many leisure travelers ride to eat. Every top operator has great food with local flair, often including Michelin-starred stops, insider home-cooked meals, and winery visits. But Tourissimo, an Italy specialist, puts on four or five trips each year led by top-tier guest chefs, such as the James Beard Award–winner and TV star Mary Sue Milliken and James Beard Award–winner Jody Adams. The Chef Bike Tours are heavily regionally focused, in places like Sardinia, Sicily, Puglia, and Italy’s gourmet epicenter, Emilia Romagna. They include classes, demos, and lots of special meals. DuVine also has a deep culinary emphasis and puts on a couple of Chef on Wheels trips each year, in Italy and the United States, as well as specialty focused trips built around harvest season and truffles. tourissimo.travel

Beautiful French vineyard in Burgundy on a bright sunny day. The rows of healthy grape vines are growing on a hillside and are green and very leafy.

Aerial view of two cyclists on a winding road through California countryside and vineyards. There are houses and mountains in the background.

Gourmand

Wine Country

All the top, classic biking hot spots are in wine country, a close second is Burgundy, and B&R has dedicated local offices in both (George Butterfield lives in Burgundy, where he has his own vineyards). The gold standard tour is Burgundy Wine Country Biking. But oddly the company does not operate scheduled trips in America’s top destination: California wine country. Backroads, the nation’s oldest active travel specialist (1979) has the most options here, with multiple wine country trips of varied difficulty and length. backroads.com

Three cyclists riding bikes on a winding road through the countryside and vineyards of Piedmont California. There is a brick wine cellar in the middle of the vineyard.

A traditional wooden yacht sailing in a large body of water with mountains in the background.

Bike By Boat

Europe

A hot trend has been using boats instead of hotels, which many travelers love because of the two-in-one vacation concept and the fact that you unpack only once, without constantly changing hotels. Most top companies now offer European river cruise trips, but none more than Backroads, which takes the concept global and uses top luxury lines like AmaWaterways. Backroads’ river destinations include Bordeaux, Portugal’s Douro River, the Rhine, Holland and Belgium, a Danube trip that cycles through five countries, the Mekong (Vietnam, Cambodia, and Laos), and the historic, epic Seine River Cruise from Paris to Normandy, including Versailles and expert-guided private tours of World War II sites.

DuVine explores niches that competitors don’t offer, and some of its very best trips use sailboats and yachts. These offer the same one-stop lodging appeal while visiting islands with amazing cycling that are not otherwise accessible. The stars are a trio of trips in Turkey and Greece, based out of the Turkish beach resort Bodrum on chartered gulets—the classic, Turkish wooden yachts that are stable and spacious, around 90 feet for just six couples. No other North American company offers cycling trips in these lightly visited but gorgeous destinations, and they are a prime choice for boat lovers or anyone looking for something different. The star is the Croatian Isles Yacht + Bike Tour.

Two people riding bicycles on a gravel covered dirt road next to a rocky mountain and a body of water. There are grass covered mountains in the distance.

Gravel Grinding

Worldwide

For several years, the fastest-growing segment of cycling has been gravel grinding: riding slightly heavier duty road bikes with beefier tires on dirt and gravel roads. The main appeal is greatly reduced auto traffic, while getting farther into nature, and while it’s more physically demanding because of increased rolling resistance, it is not technical like mountain biking. The world’s most famous gravel riding is on the Strade Bianche, or “white roads “of Tuscany, hundreds of miles of lesser-trafficked, white gravel roads hidden in plain sight in a beloved—and otherwise crowded—tourist hot spot. This is a fast-emerging pilgrimage, and currently Tourissimo is the top Italy specialist leading scheduled, guided group trips, including the Tuscany Strade Bianche. DuVine has released a detailed, guided itinerary (also offered as a private tour) and Gray & Co. does custom trips here with a high degree of luxury. One of the world’s best resorts, Rosewood Castiglion del Bosco, sits on a white road in the heart of the area. Gray & Co. has also been doing a lot of trips based out of guest ranches in Montana and Wyoming, and has seen an uptick in exotic gravel-centric destinations such as Iceland. Thomson Bike Tours, best known as the official premium tour operator of the Tour de France, also does a scheduled group Tuscany trip. But gravel riding is becoming wildly popular in bucolic spots around the world, such as Vermont, where more than half the state’s mileage of roadways remains unpaved. No top company has jumped into this category more than Thomson, with gravel trips in many destinations including Scotland, Iceland, Spain, Bali, Morocco, and Portugal. thomsonbiketours.com

Two people riding bicycles on a paved road overlooking a harbor and city with many tall skyscrapers. There are mountains and ocean in the distance.

In the foreground, there is a large wooden table set for a meal with glasses, plates, bowls and glasses. In the background there is a view of mountains and houses in Verona, Italy.

Overhead view of three cyclists riding on a narrow, winding paved road through rocky mountains next to a large body of water.

Bespoke, Ultra-Luxury

Almost Anywhere

Gray & Co. is the only company to ever win Travel + Leisure’s Best Tour Operator in the World without offering any tours—at least not off-the-rack. They have no scheduled departures and do nothing but bespoke, one-off trips for high-net-worth clients, including frequent, repeat customers with preferences for travel by private jet. As founder Cari Gray puts it simply, “No one else does what we do, period.” Staff-to-guest ratios are the highest in the business and every activity, hotel, and meal is highly curated. Group interests are foremost in trip planning—one participant might cycle all day while another rides for half and then meets with an artist, astronomer, historian, chef, or bird-watcher to pursue their individual passion. Gray’s clientele have typically done all the standard itineraries and are looking for the best of the road less traveled. She is an expert on hidden-gem cycling hot spots such as Mallorca, Colombia, and Argentina, and very high on riding in South Africa—which can be easily combined with a luxury safari. Other favorites include Scotland, Japan, and New Zealand/Australia, but she has run active travel trips even to places unknown for sweat or exertion, including St. Barth. From $4,000/person/day; grayandco.ca

Photo Credits: Courtesy Backroads/Andrew Opila; Butterfield & Robinson/Rosapaola Lucibelli; DuVine/Gwen Kidera; Backroads/Russell Grange; iStock; DuVine/PatitucciPhoto; DuVine/Gwen Kidera