U.S. citizens still need to jump through a few hoops to visit Cuba, but as visitors from around the world know, this island offers some amazing opportunities for cultural exchange. Havana is a mix of old-world architecture and of-the-moment culture. Head out of the capital city to the small town of Trinidad to see more Spanish colonial architecture. It’s a UNESCO World Heritage Site and a fantastic home base for a visit to the Valley of the Sugar Mills, a pocket of land that formerly served as the center of Cuba’s sugar industry.

Puerto Rico offers the perfect balance of rum-soaked nightlife and tranquil retreat. The Spanish colonial buildings of San Juan set a perfect backdrop for a day of shopping and sightseeing. Hike the massive El Yunque rainforest to see waterfalls, stone towers, and colorful Puerto Rican wildlife. As far as beaches go, it doesn’t get better than the private sands of Isla de Vieques – particularly Mosquito Bay, where by moonlight the water glows blue-green thanks to magical microorganisms.

The festive city of San Juan is the perfect place to experience true Puerto Rican culture. Get to know its roots by exploring the vibrant neighborhood of El Viejo San Juan (Old San Juan), which consists mostly of Spanish colonial buildings. Flesh out your self-guided history lesson with a visit to El Castillo San Felipe del Morro, a 16th century citadel that’s a UNESCO World Heritage Site. Then reward yourself with a cooling dip at Luquillo or Carolina Beach, then a tasty tour of the Bacardi rum plant.

Topnotch golf courses, art galleries and seals share the dramatic oceanside landscape of La Jolla, an affluent community 15 minutes from downtown San Diego. Swimmers, snorkelers and kayakers dip into La Jolla Cove, where the protected waters shield an abundance of bright orange Garibaldi fish and sea caves indent the cliffs. The Museum of Contemporary Art San Diego, the family-friendly Birch Aquarium and the acclaimed La Jolla Playhouse deliver breaks from the sun.

The Hawaiian island of Maui is a destination for true nature lovers. The ethereal bamboo forest and churning waterfalls in Haleakala National Park can be explored via the Waimoku Falls Trail. Stretch out on warm, golden sands or hit the surf for an unforgettable windsurfing or snorkeling session. Driving the scenic road to Hana along the island’s northeastern shore will be among the most spectacular journeys of your life. Time stands still at the Hawaiian village of Keanae, definitely worth a visit.