Founded by the Spanish in 1521, Puerto Rico’s capital is the second oldest European settlement in the Americas. Modern San Juan is a bustling city, home to over a third of the island’s population, but the cobbled streets of the Old Town remain the biggest tourist draw.

Laid back and low key, Saint Kitts is an island typified by rolling green hills, characterful beach bars and the lingering remnants of the sugar cane trade that once dominated here. Attractions include the UNESCO-listed Brimstone Hill fortress, the 18-mile Scenic Railway and the faded Georgian elegance of the capital, Basseterre.

Castries, Saint Lucia’s diminutive capital, is home to some interesting markets and colonial buildings. The island’s highlights are situated elsewhere, however, and we’d recommend either heading south towards Soufrière, where the iconic Piton mountains guard a beautiful bay, or north to the bars, restaurants and beaches of Rodney Bay.

The island of Dominica stands out from the rest of the Caribbean, a rugged natural paradise that remains blissfully free of mass market tourism. The capital, Roseau, is pleasant enough, but the island interior offers so much more, including thick jungle, bubbling hot springs, cascading waterfalls and abundant birdlife.

The busiest and most developed of the Virgin Islands, St. Thomas is nevertheless blessed with typically Caribbean good looks. The main town, Charlotte Amalie, is situated on a perfect natural harbour, and in its colonial heyday its warehouses were filled with indigo, tobacco and cotton.

Downtown Miami is a destination in its own right, with a host of world class galleries, but it's still Miami Beach that draws the biggest crowds. The Art Deco district around South Beach is very much back in vogue, with new restaurants, bars and luxury developments sprouting up all over the place.

Formerly home to a US military installation, Great Stirrup Cay was purchased by Norwegian Cruise Line in 1977, and now provides a private beach retreat for guests of Norwegian, Regent and Oceania. You can choose to just kick back and relax, or enjoy activities including kayaking, snorkelling and stand-up paddleboarding.

King’s Wharf is the port of choice for the larger cruise ships that visit Bermuda, originally built as a base for the British Navy. Attractions in the immediate vicinity include the National Museum of Bermuda and the Arts Centre, and you don’t have to travel far to find one of Bermuda's beautiful pink sand beaches.

Ponta Delgada is the capital of São Miguel, the largest and most populous island of the Azores. Founded in the 15th century, the city is home to elegant architecture and some excellent restaurants, though the main attraction is the tranquility and natural beauty of the surrounding countryside.

Málaga boasts plenty of chic restaurants and bars where you can ease into the rhythms of life in southern Spain, before exploring sights including the intriguing, unfinished Gothic cathedral, and a museum devoted to the city's most famous son, Pablo Picasso.

Cartagena was founded by the Carthaginians around 227 BC, who named it after their home city in North Africa. These days the city is best known for its well-preserved Roman theatre, which was remarkably only discovered in 1987, in spite of its location in the centre of town.

Mallorca is renowned for its beaches, ranging from big, bustling resorts to small, secluded coves. The island interior offers ruggedly beautiful scenery and quaint little towns, while the charming capital, Palma, boasts an attractive old quarter dominated by the imposing Gothic cathedral.

The UNESCO World Heritage-listed centre of Naples rewards exploration, and in addition to the many cultural treasures waiting to be unearthed Neapolitans are rightly proud of their food; this is where you’ll find the best pizza in Italy. The city also acts as a gateway to the fascinating remains of Pompeii and Herculaneum, and the beautiful Amalfi coast.

One of the world’s great cities, Rome continues to dazzle and delight visitors with a potent mix of architectural marvels, continent-defining history and buzzing nightlife. The Colosseum, the Vatican and the Forum are among the big ticket items, with the crowds to match, though in truth you will find history around almost every corner.

The picturesque little town of Amalfi was once a major Mediterranean naval power, but a devastating earthquake in 1343 cut the city down in its prime and destroyed most of its historic buildings. These days, of course, Amalfi is best known for the eponymous stretch of stunning coastline on which it sits.

Busy, noisy and a little bit scruffy, Catania is Sicily’s second city, poised perilously in the shadow of Mount Etna. In recent years gentrification has taken hold, and the city’s many beautiful palazzi and baroque churches have been restored to their former glory. Eating out here is also a real treat.

Corfu, known as Kerkyra in Greek, is a beautiful island of verdant hills and rocky coves, and away from the more crowded resorts it remains a sleepy and idyllic place. Don’t miss the picturesque Venetian architecture of Corfu Town, a UNESCO World Heritage Site.

The little seaside town of Katakolon, on the western coast of the Peloponnese, is the gateway to ancient Olympia, birthplace of the Games and the place where the Olympic flame begins its journey every four years. Make the most of your visit with a guided tour of the ruins, and don’t miss the treasures of the Archaeological Museum.

The volcanic island of Santorini (known officially as Thira) is one of the most spectacularly beautiful in the Mediterranean. The pretty village of Oia, with its whitewashed houses and windmills tumbling down the hillside, is particularly photogenic.

Glamorous Mykonos is the most popular of the Cyclades islands, well known as a haunt of the rich and the famous. It’s also the gateway to the nearby island of Delos, home to one of the most important archaeological sites in Greece.