Greater Antilles Hiking Trips

Explore the intriguing island of Cuba on this active 8-day People-to-People multisport tour. Bike, hike, and kayak wild coastal sites and tranquil countryside. Experience great colonial cities including Havana, Cienfuegos, Trinidad, and Sancti Spiritus. Discover Cuba's history, rich traditions, and dynamic present on this Cuba multisport trip.

Rolled cigars, rum spiked with sugarcane juice, and colorful vintage cars - these are the icons of Cuba that await you on this 5-day People-to-People classic Cuba tour. Find yourself immersed in legendary Cuban culture as you explore legendary Havana, the tobacco mecca Vuelta Abajo, and breathtaking Valle de Viñales.

Discover natural beauty and rich Cuban heritage on this 8-day People-to-People walking tour in Cuba. Visit Cienfuegos, Trinidad, Playa Larga, Vinales, Havana, and five parks & reserves. Explore by foot and encounter local experts, farmers, and artists as you gain insight into their history, traditions & vibrant culture on this highlights Cuba trip.

A cycling tour through western Cuba takes you off the well-traveled tourist track and onto roads where the island's rich history isn't just remembered—it is lived every day. It reveals Cuba’s greatest resource and truest legend: its people.

Pick up your 4x4 and set off into the Dominican Republic's central mountains for an active 8-day adventure. You drive over high mountain passes, explore coffee plantations, and rappel down canyons. The trip culminates in a challenging 2-day trek to the summit of Pico Duarte, the highest peak in the Caribbean.

Depart from San Juan and explore Caribbean islands on an 8-day cruise aboard Silver Dawn. Visit St John, Gustavia, Antigua, Martinique, St Kitts, and Jost Van Dyke. Swim in clear waters, snorkel vibrant reefs, hike rainforest trails, and relax on white sand beaches. Discover a mix of nature, culture, and coastal views.

Spend 15 days driving the Dominican Republic's north coast, from the colonial streets of Santo Domingo to the fishing village of Punta Rucia, the surfer town of Cabarete, and the beaches of Las Terrenas on the Samana Peninsula. This self-drive tour combines a guided city tour, snorkeling, and open coastal roads with free time at each stop.

This 15-day self-drive tour crosses the Dominican Republic from Santo Domingo's Colonial Zone to the cool highlands of Jarabacoa, the surf town of Cabarete, and the beaches of the Samaná Peninsula. Along the way, you raft rivers, hike to waterfalls, bike through history, and explore secluded coves reachable only by boat.