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For nearly 400 years, the Netherlands and France have shared the island known as St. Maarten on the Dutch side and St. Martin on the French. Home to 37 beaches and an array of tropical experiences, the island’s dual cultural profile sets it apart from other Caribbean destinations. Philipsburg, the capital of the Dutch side, is a bustling port with a lively waterfront, colorful shopping district, casinos, and restaurants serving international fare. Water sports, like sailing, and rainforest explorations are all within easy reach of its docks.

A narrow waterway separates Guadeloupe’s two largest islands, whose wing-like shapes inspired the nickname – “le papillon,” or butterfly – for this overseas department of France. The busy port town of Pointe-à-Pitre sits on the eastern island of Grande-Terre near the bridges to Basse-Terre, offering easy access to both. Grande-Terre is known for beautiful sandy beaches, the most popular along the reef-sheltered southern coast, and restaurants serving Guadeloupe’s best Creole cuisine. Basse-Terre is forested and mountainous – the active volcano La Grande Soufrière is the tallest peak.

This postcard-perfect destination, with its pastel-colored houses encircling the port, may be one of the most photographed in all of Italy. If you can take your eyes off the scenery, there is much to explore in and around Portofino. The 12th-century Church of St. George and the medieval Castello Brown both afford spectacular views of the harbor. A long, scenic hike or a short boat ride takes you to the restored 11th-century abbey in San Fruttuoso. Northwest of Portofino lies Genoa, filled with museums, palaces and the grand Cathedral of San Lorenzo.

Progreso boasts the world's longest pier, which juts nearly five miles into the Gulf of Mexico and anchors to the oceanfront amidst a gorgeous beach with a promenade that itself stretches a mile. Standing sentry over it all is the 120-foot Faro de Progreso, an active lighthouse built in 1893. Progreso has a beach-town vibe, and the center is easily explored on foot. At the biological reserve of El Corchito, observe lush flora and fauna and take a dip in one of the Yucatán’s famous cenotes – collapsed caverns that created freshwater swimming holes.

An ecological paradise of unbridled diversity, Costa Rica certainly lives up to its name, which means “rich coast.” The city of Puerto Limón has a few attractions, including the waterfront Parque Vargas and an interesting ethnohistory museum, but most visitors head to one of the many astounding national parks outside the city. A cruise through the canals of Tortuguero National Park offers the chance to observe endangered sea turtles, sloths, monkeys and even jaguars.

Tortola is at the heart of the British Virgin Island’s world-renowned sailing culture. Long, narrow and just over 21 square miles in area, the largest island of the BVI boasts a quintessentially Caribbean coastline of secluded white sand beaches, hidden coves and great natural anchorages. Inside a horseshoe-shaped harbor, the BVI capital of Road Town is the friendly, laid-back center for commerce, dining on fresh seafood and exploring nearby islets, tiny cays, reefs and dive sites.

Rugged mountains, rainforest, black sand beaches and natural wonders: this is Dominica, the Nature Island. Volcanoes forged the striking interior of high peaks, deep gorges, rivers and waterfalls. Geothermal forces are still at work, from roiling the waters of Boiling Lake to blowing bubbles at Champagne Reef. The dramatic underwater topography of boulders, plunging stone walls and ancient craters is filled with colorful tropical fish, making for great diving and snorkeling as well as whale watching.

The Samaná peninsula is the Dominican Republic’s natural treasure, a region of verdant mountains, waterfalls, a beautiful bay and miles of pristine beaches. The port town of Santa Bárbara de Samaná overlooks Samaná Bay, where the annual winter gathering of thousands of Atlantic humpback whales is the top attraction. At the bay’s western end, Los Haitises National Park preserves and protects a diverse collection of subtropical plants and birds amid the forests and mangroves. Samaná’s famous beaches are on the northern coast along the Atlantic.

Nestled at the foot of the world’s highest coastal mountain range, Santa Marta was founded in 1525 and is the oldest inhabited city in Colombia. Likewise, the city’s whitewashed cathedral claims to be the country’s oldest church. The Museo del Oro tells the even earlier history of the region’s indigenous people, who were skilled goldsmiths, as well as the story of Spanish colonization. The story continues with Simón Bolívar, the “Great Liberator,” who led Colombia and other South American countries to independence from Spain.

The capital of the Dominican Republic, Santo Domingo is a big, energetic city with a vibrant urban culture. At its heart is the walled Zona Colonial, a compact district of cobblestone streets and graceful plazas lined with incredible heritage architecture, some dating to the early 1500s. Sights include the Catedral Primada de América, the ruins of the San Francisco monastery, and the original Spanish-built fortifications, as well as museums, shops and eateries.