Looking for a challenge? Backroads has long been a favorite of riders who love big days in the saddle. With more than 20 biking trips that include Level 5 routes—our toughest option—these adventures will thrill guests who want to log longer miles, power up sustained climbs and enjoy the satisfaction of pushing their limits.
Each of these six-day trips tops 240 cumulative miles and knocks out as much as 27,700 feet of elevation gain (whoa, Cyprus!), should you choose to ride the rigorous routes. Want to raise the bar even higher? Opt for an acoustic departure, what we call Unplugged, and pedal under your own power, without any e-boosting assists, alongside others who also prefer to use just their legs and lungs.
What sets Backroads apart is choice. You can challenge yourself on our hardest routes while traveling with partners, friends or family who prefer shorter rides or an e-bike (or, better yet, one of our new performance e-bikes), while still sharing the same great hotels, meals and moments off the bike.
Here are seven of the most challenging Backroads biking tours in 2026, with more options on the horizon in 2027.
California Wine Country
Total Mileage: 269
Total Elevation Gain: 16,800 feet
Challenges: A 62-miler on Day 2; the steep-but-short Franz Valley School Road uphill; the most cumulative mileage of any Backroads biking trip
The Payoff: Looking for the best biking in California? You got it. Pedal power will take you from San Francisco to the charming Napa town of Calistoga via majestic old-growth redwood forests, the Russian River, the Sonoma coast and the nation’s most renowned vineyards. Active mornings and afternoons are balanced by evenings at award-winning luxury hotels—including the Lodge at Bodega Bay and Solage, an Auberge Resort—and wine tastings each day.
Guests Say It Best: “I have never before done that many miles back to back, but with the excellent lunches and ‘snack roads’ support stops, it was totally doable. And weirdly addictive. Biking through wine country was heavenly. In the afternoons we did massages, wine tastings and relaxed,” wrote Laura Vricella.
Discover Backroads’ California Wine Country Bike Tour
Tuscany
Total Mileage: 262
Total Elevation Gain: 23,400 feet
Challenges: A 65-miler on Day 2, with 5,700 feet of elevation gain; Monteluco Challenge, a four-mile leg-burning climb on an 8 percent grade
The Payoff: Biking in Tuscany is hill-filled, which makes it so picturesque but also tough on the thighs if you’re pedaling without e-assist! We’ve been leading Tuscany bike tours for decades and have perfected this trip, not to mention established wonderful relationships with locals whom we’ve come to love (and vice versa). Highlights include riding through Val d’Orcia, a UNESCO World Heritage landscape with cypress-lined lanes, climbs that top out at medieval villages with views for miles, thermal pools that ease tired muscles and tastings of the region’s most remarkable wines—Brunello, Chianti Classico and Vino Nobile di Montepulciano, among others.
Guests Say It Best: “Each day unfolded like a postcard—rolling hills draped in vineyards, sun-drenched olive groves and medieval hilltop towns. Routes were perfectly curated, challenging just enough to earn that next glass of Chianti,” wrote Janie McLaughlin. “We dined on farm-to-table feasts, indulged in handmade pasta and shared laughter over long, rustic tables with local wine flowing freely. This wasn't just a bike trip—it was an unforgettable immersion into the heart and soul of Tuscany.”
Discover Backroads’ Tuscany Bike Tour
Southern Spain’s Andalucia
Total Mileage: 258
Total Elevation Gain: 22,900
Challenges: Day 2’s 60-mile route with 6,300 feet of elevation gain
The Payoff: If you follow the Vuelta a España, Spain’s Tour de France, you’re familiar with Andalucia. The region is synonymous with long climbs and dramatic terrain, and we bookend our Andalucia bike tour in two of its most historic cities, Sevilla and Granada. Visit a cork-oak forest and the remote, wild Sierra de las Nieves National Park, home to boar and ibex. Pause from pedaling to hike the thrilling gorge of Caminito del Rey. And kick back at day’s end at the absolutely stunning La Bobadilla Hotel, modeled after the whitewashed pueblos blancos dotting the region.
Guests Say It Best: “If you want challenging climbs on an Unplugged bike, this tour has them,” wrote guest Karen Fienberg. “The gorgeous scenery will take your mind off the suffering! Extremely fun descents, too.” Backroads employee Annette Wegscheider, who took the trip, added: “Doing some of the climbs included in the Vuelta puts the pro riders' performances in perspective!”
Discover Backroads’ Southern Spain’s Andalucia Bike Tour
Cyprus
Total Mileage: 253
Total Elevation Gain: 27,700
Challenges: The most total elevation gain of any Backroads biking trip; back-to-back days with 7,000 and 6,600 feet of elevation gain
The Payoff: Who knew that biking in Cyprus could be one of the hardest cycling adventures in Europe? We’re thrilled to offer this new trip and show you the magical terrain, culture and cuisine of this binational Mediterranean island. Our route along quiet, well-paved roads sets the stage for scenic, ever-changing views: turquoise coasts, pine and cedar forests, Mount Olympus (mythical home of the Greek gods), stone monasteries, terraced olive groves, ancient ruins. Sip Cypriot wine and sample shared plates of grilled Halloumi and dozens of other meze dishes. And expect to return home with a tan—Cyprus enjoys an average 320 days of sun annually.
Guests Say It Best: Our first Cyprus Bike Tour departs in May, with reviews to follow. Initial response to this trip has been popular, with several dates already sold out, so view the remaining available departures and get ready to bike with our crew!
Discover Backroads’ Cyprus Bike Tour
Provence Wine Country to Luberon
Total Mileage: 252
Total Elevation Gain: 21,800
Challenges: Day 3’s 60-mile ride with 7,500 feet of elevation gain; tackling formidable Mont Ventoux, the bucket-list Tour de France climb
The Payoff: A number of Backroads biking guests are drawn to this Provence Bike Tour specifically to ride Mont Ventoux, a legendary Tour de France summit regularly featured in the famous race. But this trip has other iconic moments on and off the road: we bike past lavender fields, stay at a Relais & Châteaux property, have a private tasting of 100-point wines, pedal in one of France’s wildest gorges and learn how to play pétanque. In short, it’s an amazing itinerary that ties together popular Provence and lesser-known Luberon for a defining bike experience in the South of France.
Guests Say It Best: “This was by far the most difficult and yet most exhilarating vacation we have ever taken. The challenge of the Provence countryside was exciting and such a feeling of accomplishment,” said guest Connie Carlson.
Discover Backroads’ Provence Wine Country to Luberon Bike Tour
Spain’s Mallorca
Total Mileage: 245
Total Elevation Gain: 22,200
Challenges: Ample hills and serpentine sections, notably Sa Calobra, a roller-coaster road of hairpin turns carved into cliffs; back-to-back days with 5,500 and 5,100 feet of elevation gain; a 59-miler on day two
The Payoff: An extraordinary exploration that encompasses nearly all of the island—the southern capital of Palma and its beautiful bay; the rugged, terraced interior; the sparkling west coast; and a grand finale on the northern Cap de Formentor. Premiere hotels in stunning locales, farm-to-table (and boat-to-table) dishes and incredibly friendly locals make for an unforgettable Mallorca bike tour and, we’d argue, some of the best biking in Spain.
Guests Say It Best: “Cycling in Mallorca is quite simply hard to beat! This trip is tough with the climbing, but the views, the road quality and the hotels/food make it all worth it. Highly recommend!” said Christopher Jackson. Another guest, Ken Finkelstein, added, “This Mallorca trip was reputed to be one of Backroads' best, and it more than lived up to this advance billing. Truly extraordinary. Amazing scenery, fantastic weather and superlative biking, with some challenging uphill climbs and truly exhilarating downhills, usually with a spectacular view.”
Discover Backroads’ Spain’s Mallorca Bike Tour
A Taste of Camino de Santiago
Total Mileage: 243
Total Elevation Gain: 23,300
Challenges: Day 4’s 54-miler with 5,400 feet of elevation gain
The Payoff: Starting in Santiago de Compostela, Spain, and ending in Porto, Portugal, ride the most scenic sections of this world-famous pilgrimage route. Historic hotels await at the end of each ride, from a medieval castle on a surf-battered bluff to a dreamy Baroque villa. Galician wine is on pour, pine forests offer quiet contemplation and thermal waters await the hour you pull in at the end of an exhilarating day. A Camino de Santiago Biking Tour that sets the standard.
Guests Say It Best: “Between the scenery, food, bike rides, and our incredible leaders, it's hard to pick a favorite part of the trip! Riding the Spanish coast and mountains of Galicia and Portugal, sampling the regional food and seeing the amazing history, culture, music and terrain of this region was an overwhelmingly positive experience,” wrote Bimal Desai, who took this as a father-son trip.
Discover Backroads’ A Taste of Camino de Santiago Bike Tour
