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.

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.

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.

Make sure to be on deck to witness sailing into one of the Aegean’s most spectacular sights: the volcanic caldera that is Santorini’s bay. Rising from the sea, the earth transforms into a wall of stone that looms in striating hues of ochres, grays and pinks. Dotted with the island’s iconic blue-domed churches, the whitewashed village of Fira hovers in the cliffs, bustling with shops, tavernas and a fine museum while clinging to the caldera’s rim.

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.

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, 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.