Discover Cuba
November 3-11, 2025
SWS Adventure begins in:
Discover Cuba on Land | 9 nights
Sail with Seth… On Land! Join us for our first-ever land-only trip to the captivating island of Cuba from November 3 to November 11, 2025. This extraordinary expedition invites you to explore the rich tapestry of Cuban culture and history in a way that brings you face-to-face with the vibrant life of the island.
Discover how much of Cuba’s pre-Castro heritage has been beautifully preserved as you wander through the colorful colonial cities of Trinidad and Cienfuegos. Experience the charm of cobblestoned streets, relax in lush mountain surroundings, and snorkel in the tropical coral reefs of the Bay of Pigs, a destination famed for its stunning underwater biodiversity. In Havana, immerse yourself in the 500-year-old city, taking time to visit Ernest Hemingway’s historic home and understand the profound impact he had on the island. Throughout your travels, engage closely with the people who call Cuba home—interact with coffee growers, artists, dancers, and historians, and gain insight into the everyday lives of Cubans.
Rest assured, all interactions and activities during your time in Cuba are fully compliant with the U.S. government’s “Support for the Cuban People” general license guidelines. Our partnership with Classic Journeys ensures that your trip is 100% legal and that all necessary record-keeping for the Office of Foreign Assets Control (OFAC) is managed on your behalf, allowing you to focus on what truly matters—experiencing the beauty and warmth of Cuba.
Your journey begins in Miami, Florida, where you’ll fly to Havana, setting the stage for an unforgettable exploration of this enchanting island. After immersing yourself in Cuba’s rich culture and stunning landscapes, you’ll return to Miami to reflect on your incredible adventure. Don’t miss this unique opportunity to experience Cuba like never before—join Sail with Seth for this remarkable land journey!