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.

Although Tobago straddles the border of the Caribbean Sea and Atlantic Ocean, the island feels quintessentially Caribbean thanks to its laid-back, carefree vibe. In the capital of Scarborough, the locals may bustle through the central market and esplanade, which are worth a stroll to shop for authentic souvenirs, but just outside of town the pace of life relaxes. The golden, palm-lined beaches along the island’s many bays are perfect for sunning, swimming and “liming” – the local slang for relaxing with friends.

Only small ships and yachts can access the harbor of Sète, which is one reason this enchanting French port has retained its many charms. The birthplace of numerous artists, including poet Paul Valéry and singer-songwriter Georges Brassens, Sète has a rich artistic heritage and its museums pay tribute. Colorfully painted façades line the town’s canals, which include the northeastern entrance to the Canal du Midi, a UNESCO World Heritage site linking the Mediterranean and Atlantic through southern France. Several other UNESCO sites nearby compete for attention.

Nestled in a lush valley of fruit trees and olive groves between the mountains and the sea, Sóller is an elegant and arty Mallorcan treasure that blends the quaint and contemporary. Visitors may stroll on picturesque cobbled streets and sun worship in the cafés of Plaça de la Constitució or deeply explore the nature and history that makes the Balearic Islands famous. The Church of Sant Bartomeu is a major attraction, one of many historic churches in the valley. Linking Sóller to its port is the Tranvía de Sóller, one of only two first-generation tramways to survive in Spain.