Columbus called it “the most beautiful land human eyes have ever seen.” Five hundred years later, it still has charm—though it is not a luxury destination. But today’s Cuba is a rare find for adventurous travellers: unspoiled beaches, rolling countryside, timeless architecture, fresh music, and vintage cars all dazzle against a palette of vibrant hues. And lucky for us, there are some patches of roads in good enough condition for two-wheeled explorations in Gray & Co. style.

Old Havana is the city that time forgot. Great art, architecture, music, dance, and mojitos are the rule. Two hours away, the town of Viñales features fields of tobacco nestled between dramatic limestone rocks. Bike to the coast along tranquil roads with ox and horse carts. Enjoy fresh seafood, live music, and some well-earned beach time. Near the Spanish Colonial town of Trinidad—and the newly renovated Ibostar Grand Hotel—we ride to the white sand beaches of Playa Ancon for an espresso and a dip in the Caribbean.

Please note that Americans must have a valid visa to travel legally to Cuba. For all nationalities, this is a trip that requires much advance planning to secure the best accommodations and experiences.