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.

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.

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.