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.

Salem, Massachusetts, USA

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Few American cruise destinations have a past as engrained in popular culture as Salem. Settled by European fishermen in 1626 and named for the Hebrew word for peace – “shalom” – the seaport in 1692 was anything but peaceful. Multiple attractions harken back to the days of the witch trials, including the Witch House and the Trials Memorial. The Maritime National Historic Site comprises the Custom House, the enduring wharves and buildings along Derby Street and the Friendship of Salem, a replica of the East Indiaman tall ship launched in 1797.

Rostock (Warnemünde), Germany

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Your yacht docks in Warnemünde, a charming resort town with a popular beach, a pretty promenade and gabled fishermen’s houses. Nearby Rostock enchants with its university established in 1419, St. Mary’s Church with its famous astronomical clock, the 13th-century Town Hall and the quaint Old Town. You might also travel inland to the quintessential fairy-tale castle of Schwerin Palace.