On the east coast of Terceira in the Azores, the port of Praia da Vitória offers a gateway to fine beaches, sea pools, and the sight of “happy cows” - the Ramo Grande cattle that graze this island's pastures year-round. But the star of this show is the UNESCO World Heritage site of Angra do Heroísmo, the archipelago's oldest city, where you can lose yourself in cobbled streets and attractive squares, and see baroque cathedrals, maritime forts, and other landmarks that are a testament to the island's prosperity during the Age of Discovery. Learn more about it at the Museum of Angra do Heroísmo. Terceira's volcanic soil nurtures tasty produce. Try tempting rustic dishes such as alcatra, a clay pot stew, washed down with a glass of delicious local wine.

Striking, atmospheric and delightfully unspoilt, the streets of the Azorean capital are lined with historic mansions and houses, blazing white against the cobalt sky, edged and decorated with traditional black basalt stone. A fantastic destination for wildlife lovers, in spring and summer boats head out of here each morning to spot the dolphins, whales, and sea turtles making their way through the Atlantic waters. But the city's three lush botanic gardens, beautiful Azulejo tiling in the ornate churches, and shorefront boardwalk lined with boutiques and restaurants, makes it ideal to visit at any time of year.

Don't be fooled by Horta's isolated location in the Atlantic on the Azorean island of Faial – for centuries, this fascinating city has seen many come and go, playing host to sailors of every stripe, from intrepid explorers to pleasure seekers and naval seamen. The historic tangle of streets, which winds around former merchants' houses and statuesque churches, bookended in time by the 16th-century defensive walls and the gleaming contemporary marina, is perfect for exploring on foot. Horta's rich, seafaring heritage is best experienced with a sunset GT at the world-famous Peter Café Sport – a bar that has been welcoming sailors to the island since 1918.

St. John's, the capital city of Antigua and Barbuda, is a vibrant and culturally rich destination nestled in the heart of the Caribbean. With its picturesque harbor, historic landmarks, and lively atmosphere, St. John's offers visitors a diverse array of experiences. The cityscape is defined by its pastel-colored buildings adorned with intricate colonial architecture, creating a charming backdrop for exploration. As you wander through the streets, you'll encounter bustling markets, quaint boutiques, and inviting cafes serving up local delicacies. One of the highlights of St. John's is its historic sites, including the iconic St. John's Cathedral, a masterpiece of English Baroque architecture, and the ruins of Fort James, which offer panoramic views of the coastline. The Museum of Antigua and Barbuda provides insight into the island's rich history and culture, showcasing artifacts and exhibits spanning centuries. For those seeking relaxation, St. John's boasts stunning beaches with powdery white sands and crystal-clear waters. Dickenson Bay and Runaway Bay are popular spots for sunbathing, swimming, and water sports such as snorkeling and sailing.

Great Harbor, a deep, softly sweeping indentation on the south side of the island, treats visitors to an eyeful of tropical loveliness and a host of amenities. Lined by rustic, character-filled shops and eateries, the harbor-front beach offers a real feel for the Caribbean. Standbys like Christine's Bakery (serving fresh breads and sticky buns) and Foxy's (one of the best-known beach bars in the Caribbean) are so humble that they might be overlooked by the uninitiated passerby.

The capital of Puerto Rico is a proud place that makes a strong impression even on approach. Sail into harbor and spot the sights: El Morro, a 16th-century citadel which once defended the island from attack; Castillo San Cristobal, a fearsome fortress built to scare away invaders; and La Fortaleza, impressive home of the Governor. Once ashore, step back in time along cobblestone streets and through squares flanked by beautiful pastel-colored Spanish colonial buildings. Find a shady perch in one of the cafés, bars or restaurants to watch the world go by with a piña colada – invented here in the 1950s. There are good sands to relax on, too, such asIsla Verde Beach. Browsing the art galleries on Calle del Cristo, watching the street performers on Paseo de la Princesa, birdwatching in El Yunque, the only tropical forest in US territory.