Vibrant and packed with Victorian mansions, Costa Rica's rowdy, bustling capital was built on the profits of the coffee trade and working "golden bean" plantations still surround the city. Try freshly roasted local beans at Mercado Central. For shinier gold, visit the Museo del Oro. Many renovated landmarks now house stylish hotels. Usually viewed as a hub, rather than a destination, nightlife is concentrated in Spanish village-inspired El Pueblo. Don't miss the elegant 1897 National Theater.

The Cayman Islands are made up of three islands: Grand Cayman, Cayman Brac and Little Cayman. The largest, Grand Cayman has a cosmopolitan vibe, gourmet restaurants, world-class diving and the famous Seven Mile Beach. Cayman Brac is a nature lover's heaven of stunning diving and breathtaking walks along the rocky bluff. The smallest island, Little Cayman is home to just 150 people. Visitors enjoy the relaxed atmosphere and diving, especially Bloody Bay Wall, considered one of the world's best wall dives.

Situated on Grand Cayman’s west shore, Seven Mile Beach actually now measures only 5.5 miles. But its gorgeous clear waters and coral sands still lure visitors from around the world. Beach bars, such as the Royal Palms, provide drinks and a lively atmosphere, and restaurants abound. Swim with friendly stingrays at Stingray City, shop Seven Mile Shops, snorkel and scuba in the enticing waters around Cemetery Reef. Visit nearby Cayman capital George Town and the fascinating Cayman Turtle Farm.

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.