Start your trip in La Gomera, one of the archipelago’s oldest islands, where Garajonay National Park and a rugged interior set the stage for fascinating exploration • Ride the rolling blacktop from central Alajeró to the port capital of San Sebastián—Christopher Columbus pit stopped here—passing deep volcanic ravines, terraced fields and palms and pausing for a delicious island lunch • Get schooled in the local whistled language, pottery practices and cooking • Wheel to incredible viewpoints and through an ancient laurel forest filled with giant ferns and birds like the Island Canary • Dine at a historic clifftop parador with views over the Atlantic to Tenerife.

Hop a quick ferry east to Tenerife, the Canaries’ largest island and home to Spain’s tallest peak—a volcano whose slopes we’ll skirt today on various routes • Relax at a winery during a leisurely lunch that might include local specialties such as artisanal cheeses, charcuterie and island-grown fruit like dwarf bananas, which have a distinctive taste • Wheel through fragrant pine forests and almond groves • Enjoy a guided walking tour of leafy San Cristóbal de La Laguna, a UNESCO-recognized city with colorful colonial mansions and the islands’ first university.

A hill climb on 12,198-foot Mount Teide? Epic! Our scenic route up its north side is a favorite of pro cyclists, wends through a national park and sees us lunching near the top with glorious views for miles • Marvel at the diverse landscapes and flora, from native violets to otherworldly rock formations to black-sand gullies • Explore the colonial communities of Icod de los Vinos, known for its 800-year-old dragon tree and Malvasia dessert wine • Bike the serpentine switchbacks of northwestern Masca, where dramatic panoramas of a spectacular valley unfold around every bend • Kick back for some R&R (or a round of golf) at our home base, a Small Luxury Hotels of the World property • Cap things off with a final ride along Tenerife’s wild, windswept northwestern coast.