Lake Como, Italy
The punishing Colma di Sormano is part of a 42-mile loop that begins just beyond the terrazzo floor lobby of Hotel Villa Flori on the southeastern shore of the lake. The dizzying ascent, with 24% lengths, figures prominently in the annual Giro di Lombardia race, so tackle it with a rider from ComoLagoBike, whose main guide is former pro Alberto Elli.
Stay: Most of the 53 rooms of the Flori, a 19th century wedding gift from a nobleman to his daughter, offers lake views from her private balconies. But the views are even better from the rooftop spa and cedar-flanked garden, where you can load up Belgian waffles for breakfast.
Treat yourself to: Fresh Japanese whiskey with jasmine tea at the hotel Vista Palazzo’s Infinity Bar is the culmination of a world-inspired menu. Any lingering pain in your legs is almost guaranteed to ease.
The spectacular 10km Sa Calobra – where Sir Bradley Wiggins trained before winning the 2012 Tour de France – has more switchbacks than the notoriously difficult Alpe d’Huez.
Stay: The capital Palma has as many excellent bicycle shops as it does cafes and tapas bars, but the bougainvillea La Residencia, a Belmond hotel with stone architecture, terraced pools and a rugged backdrop, places its guests in the heart of the best riding on the island.
Treat yourself to: Complete an additional 20 miles on your journey by climbing the Coll de Soller. Ca’n Topa, a restaurant perched at the top, is where local runners congregate for double ristrettos and orange-infused cake.
Above the lavender fields of the Luberon valley stands Mont Ventoux, one of the royal climbs of the Tour de France. Known locally as the “Giant of Provence”, it has three roads leading to the summit; by taking the 13 miles and 5,000 feet of ascent from Bédoin, you will have the right to brag the most.
Stay: With its whitewashed houses and cobbled streets, Gordes, perched on a hill, is one of the prettiest towns in Provence. This is the house of Airelles Gordes La Bastide, an 18th century cliffside residence converted into a retreat with antique guest rooms and a 17,000 square foot Sisley spa.
Treat yourself to: Grégory Mirer, a Parisian transplant, conjures up simple but spectacular dishes at the Michelin-starred restaurant Hôtel les Bories & Spa, think leg of lamb with candied eggplant and fresh herbs from its garden.
The vistas get more and more spectacular as you make your way to Kotor Serpentine, a single lane road that winds its way up the slopes in a tight series of 25 hairpins as it gains nearly 3,000 feet of altitude.
Stay: the One & Only Portonovi recently opened on the magnificent Bay of Kotor, where rugged mountains crash against a sapphire shore. Explore the resort’s 60-hectare seaside, enjoy its five swimming pools or admire all the Mediterranean splendor from its floor-to-ceiling windows.
Treat yourself to: Whether you continue to drive to Lovcen National Park, home to a mausoleum atop the highest massif in the region, or turn around for a freehand descent, plan a stop at the mountainside restaurant The Adriatic Bride. His Njeguski prsutMontenegrin prosciutto is smoked with beech wood and owes its unique salinity to the sea breezes that blow in the alpine air.
Thanks to its extensive network of dirt roads, the wind strafed Tinos is best explored by gravel bike. Take the 10km trail up Mount Tsiknias, which boasts steep ramps and a craggy summit that reliably rises out of the low cloud cover.
Stay: The most famous Athenians unplug on this charming and un-touristy island 15 minutes north of Mykonos. Sleep at least Infinity View Tinos, where most of the 16 suites, stacked like sugar cubes above the coast, offer Aegean Sea views from the privacy of your own plunge pool.
Treat yourself to: Head to rock-strewn Livada Beach for a quick dip in the island’s clearest waters. There the Nikos Darmis promenade tavern (no website) serves a protein restoration froutalia omelet with wild artichoke, a heritage delicacy cultivated in the mineral-rich soil of the island.