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Tobago Cays, St. Vincent and the Grenadines

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The Tobago Cays are an eco-paradise of pristine, aquamarine waters, sparkling white beaches and amazing wildlife in the southern Grenadines. A cluster of five uninhabited cays and the surrounding barrier reefs protect seabirds, native plants, iguanas, sea turtles, colorful hard coral and tropical fish. Tobago Cays Marine Park can only be reached by a boat, which can anchor in a sandy-bottomed lagoon. From here, snorkeling and diving explorations reveal a vibrant underwater world. In the Baradal Turtle Sanctuary, get close to green and hawksbill turtles in their natural habitat.

Terre-de-Haut, Les Saintes, Guadeloupe

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Les Saintes are a volcanic archipelago of two islands and seven uninhabited islets surrounded by thriving coral reefs and clear seas. Small at just over two square miles, Terre-de-Haut is the most developed of the group, thanks to an anchorage-rich coastline of scenic bays, natural harbors, quiet beaches and charmingly picturesque villages. The ambience is decidedly low-key, and days are devoted to beachgoing, hiking, snorkeling and diving.

St. George’s, Grenada

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Grenada is the legendary Spice Isle, where nutmeg perfumes the air. Fort George guards the entrance to the colorful, pedestrian-friendly capital of St. George’s. The 18th-century garrison and the hilltop Cathedral of the Immaculate Conception offer the best views of the city and its picturesque harbor, the Carenage. To the south of St. George’s is the wide expanse of Grand Anse Beach, the main resort area.

Soufrière, St. Lucia

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St. Lucia’s iconic landmarks – the towering volcanic peaks known as the Pitons – rise over the bay and over Soufrière, the original capital established under French rule. Less than two hours by car but a world apart from British-founded Castries, Soufrière is a small town replete with charming examples of tropical colonial architecture. Anchorage here provides easy access to St. Lucia’s leading natural attractions, like the Sulphur Springs that inspired the town’s name – the steaming crater of a “drive-in” volcano.

Scarborough, Tobago, Trinidad and Tobago

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Unhurried, unspoiled and relatively undeveloped, Tobago entices and charms with its simple pleasures and languid pace. Tucked into a scenic bay on the southern coast, the capital of Scarborough has a village feel, with the town market at its center. The island’s few historic sights include the Georgian-style Court House, the seat of island government, and hilltop Fort King George, home to the Tobago Museum and great views. Tobago’s wide sandy beaches and pristine waters – perfect for sunning, swimming, aquatics and relaxing – are the main attractions.

Santo Domingo, Dominican Republic

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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.

Santa Marta, Colombia

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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.

San Juan, Puerto Rico

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San Juan, the capital of Puerto Rico, is an intriguing blend of the old and the new. Founded in 1521, the city was a key port in the Spanish colonial empire, as evidenced by El Morro, the huge fortress that guards the harbor. Behind thick stone walls, Old San Juan retains its original character of blue cobblestone streets, elegant plazas and brightly colored heritage architecture. This lively center is the city’s – and island’s – cultural hub for museums, music, dining and more.

Samaná, Dominican Republic

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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.

Roseau, Dominica

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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.