A cruise around the Caribbean is by far the best and easiest way to get a feel for the region, which has everything from large developed islands with buzzing tourist spots to tiny outposts whose charm lies in their rustic simplicity and beautiful natural surroundings. 

You ‘ll find cruise ships of all sizes here, from the world’s largest vessels to small luxury yachts. Some ships are here year-round, but most only spend winter in the islands, providing cruisers with a sunny holiday when the weather at home gets grey and cold.

Most cruises depart from the Florida ports of Miami or Fort Lauderdale, but a few start from within the islands, notably Barbados or Puerto Rico. Thomson Cruises bases a ship in Montego Bay, Jamaica; new for winter 2016-1 7, P&O Cruises’ Britannia will be embarking passengers in St Lucia.

Sailings range from short three-day trips from Florida to the Bahamas to voyages of two weeks or more, but the most common itineraries tend to be seven days, sailing either to the Eastern Caribbean (Puerto Rico, St Thomas, Barbados and Martinique), or the Western Caribbean (Cozumel, the Cayman Islands and Jamaica).

Some also visit the Southern Caribbean, with calls at islands including Guadeloupe, Grenada, Tobago and the Dutch ABC islands (Aruba, Bonaire, Curacao), while other sailings pair island calls with a trip through the Panama Canal to the Pacific Ocean.

ANTIGUA

Ships moor in the centre of the capital, St John’s, so it is easy to wander ashore to browse the shops in the modern Heritage Quay area or the more rustic Redcliffe Quay, where authentic Georgian buildings house cafes and boutiques. If you want to explore further, taxi drivers, who are also qualified tour guides, will take you to Nelson’s Dockyard, the world’s only working Georgian dockyard and the island’s most famous tourist site with restaurants and shops housed in the restored buildings. Antigua is famous for its beaches; one of the best-known, Dickenson Bay, is a 20-minute drive from the port.

ARUBA

Like its neighbours, Aruba has plenty of sun, sand and sea – in fact, some of the best beaches in the region – but that’s where the similarities with other Caribbean islands end. Where others have lush green landscapes, Aruba is desert-like, home to cacti, arid-loving aloe plants, and divi-divi trees. The capital, Oranjestad, is an easy walk from the cruise port, and has shopping and restaurants, but there are more rewarding ways to spend the day. Catamaran trips take you to the best reefs or you can ride a Seabob underwater scooter, while non-swimmers can don a diving helmet and walk through shoals of tropical fish. On terra firma, jeep, ATV (all-terrain vehicle) or Harley Davidson motorbike tours are a fun way to see the sights.

BAHAMAS

Nassau is the capital of the Bahamas and the islands’ main cruise port, though some ships call at Freeport on Grand Bahama Island. In Nassau, you’ll step ashore at Prince George Wharf and walk through the Festival Place welcome centre with its local stalls and occasional live bands. Outside are lines of ‘surreys’ offering horse and carriage rides around the capital, while just a few steps more will bring you into Bay Street and its duty-free shops and Straw Market for local handicrafts. A few streets away is the entertaining Pirates of Nassau museum. If you fancy swimming with dolphins, book an excursion to Blue Lagoon Island.

BARBADOS

Barbados is packed with attractions, from Harrison’s Cave, a subterranean complex of limestone tunnels and pools, to restored plantation houses such as Sunbury Plantation or St Nicholas Abbey. An island tour takes visitors to the top of Cherry Tree Hill, renowned for its fabulous views, and down onto the rugged east coast where Atlantic rollers sweep in. Cruise ships clock a 20-minute walk outside the capital, Bridgetown. It’s worth noting that local companies are not allowed to hawk for business at the terminal; they can only pick up, so if you want an independent tour, arrange it in advance.

BRITISH VIRGIN ISLANDS

Smaller cruise ships call at the less developed islands such as Jost Van Dyke, Norman Island or Virgin Gorda; the big ones dock at the main island of Tortola, a short walk from the capital, Road Town. Taxis are available for island tours, or head to Cane Garden Bay, a popular beach that can get very crowded if more than one ship is in. An alternative is to get on a smaller boat and explore other islands. Virgin Gorda is home to The Baths, a collection of huge rocks housing natural swimming pools and romantic hidden grottoes.

COZUMEL

This island off the Mexican coast is a real tourist trap, and also a prime location for scuba-diving excursions and boat trips. There are also full-day excursions to the mainland, to visit the important Mayan archaeological sites Chichen ltza or Tulum on the Yucatan Peninsula. The main town on Cozumel is San Miguel, accessible from the island’s three cruise piers. However, the distance varies depending where your ship is moored. The closest pier is by the city, the furthest one about five miles away.

DOMINICA

The so-called “Nature Isle”, Dominica is one of the Caribbean’s most unspoilt and undeveloped outposts able to cater for larger cruise ships. Most dock in the capital, Roseau, though some smaller vessels call at the town of Portsmouth in the north. Once ashore, there are hiking tours through the lush rainforest to waterfalls or the island’s famous boiling lake. The Rainforest tram affords a bird’s-eye view across the mountain peaks, and there are tours to Carib Territory, inhabited by one of the Caribbean’s few remaining tribes, or whale-­watching tours.

GRAND CAYMAN

Ships anchor off the capital, George Town, and tender passengers ashore – the city is a short walk from the dock and has a good selection of tourist shops. The main attraction, though, is Stingray City, a shallow sandbar where tame rays wait to be fed squid by tourists who arrive in small boats. The island is also a popular beach stop thanks to its beautiful waters and talcum powder beaches (Seven Mile Beach is the most famous), and you can snorkel or dive amid the colourful marine life. Helicopter rides give a bird’s-eye view of the island and surrounding reefs.

JAMAICA

Climbing Dunn’s River falls near Ocho Rios has to be the top attraction in Jamaica, but there are lots of alternatives if that doesn’t appeal. You can take a chairlift to the top of Mystic Mountain and ride down on a bobsleigh or glide through the treetops on a canopy tour: for a taste of the island’s history, visit Rose Hall plantation house. There are also river-rafting trips. The island (the third-biggest in the Caribbean) has four ports along its north coast – at Ocho Rios, Montego Bay, Pon Amonio and Falmouth, which caters for the larger American ships. If you’re docked in Ocho Rios or Falmouth, you’ll be in town; in Montego Bay the port is about three miles from downtown. Port Antonio in the east is used by smaller vessels.

PUERTO RICO

Cruise ships moor in the heart of the colonial quarter of Oki Sanjuan, so it’s easy to head ashore and delve into the historic Spanish roots of Puerto Rico’s capital. The maze of narrow streets, perfect for wandering, is filled with boutiques, outlets selling local crafts, and atmospheric Latino bars and cafes. When you tire of shopping, nearby historic sites include the forts of El Morro and San Cristobel. The El Yunque rainforest is an hour’s drive away.

ST KITTS

Ships moor at Pon Zante cruise port, close to the island’s capital, Basseterre, so it is easy to wander ashore and explore alone, or pick up a tour from one of the waiting taxi drivers. Their prices drop the further away you walk from the port. The top excursion is the narrow-gauge St Kitts Scenic Railway, which bumps and rattles its way along a scenic circuit through the former sugar plantations that gave the island its wealth. History buffs should visit Brimstone Hill Fortress, built more than 300 years ago when the island was under British rule and now a UNESCO World Heritage Site. Alternatively, take a short boat ride to discover St Kitts’ sleepy and pretty sister island Nevis.

ST LUCIA

Big ships visiting this lush rainforest-­covered isle moor at the capital, Castries, in the north of the island, but smaller vessels call at Soufriere or Marigot Bay in the south, and Rodney Bay or Pigeon Island in the north. Top attractions include the world’s only drive-in volcano and Tet Paul botanic garden, where there are fabulous views of the island’s iconic twin Pitons (volcanic spires). Pigeon Island, connected to the mainland by a man-made causeway, is a popular spot for swimming and snuba diving (a cross between scuba and snorkelling). The island was once a pirate hangout and ex-military base (the British built the 18th-century fort Rodney at the top of the island to keep an eye on the French fleet in Martinique). Head to Rodney Bay for the beach and fun Segway tours.

ST MAARTEN/ST MARTIN

Most cruise ships dock in Phillipsburg in St Maarten (Dutch), but some smaller ones call at St Martin (French). From the modern cruise clock in Phillipsburg it’s an easy walk into town, where you can laze on a white sand beach surrounded by bars and cafes or explore the capital’s various souvenir shops, boutiques, and casinos. There are snorkelling trips and motorbike tours. A popular excursion goes to the island’s French capital, Marigot, where, in the blink of an eye, the ambience changes from Dutch to Gallic with French-inspired shops and cafes.

ST THOMAS

St Thomas is one of the Caribbean’s busiest cruise ports and a favourite for its duty-free shopping. The capital, Charlotte Amalie, is a 10-minute taxi ride from the Havensight cruise port and a 30-minute walk from the dock at Crown Bay (of course there are plenty of taxis if you prefer to ride). The marine park Coral World is one of the island’s best-known attractions, while the St Thomas Skyride cable car offers the best views. One of the best excursions is to take a smaller boat and head off on a snorkelling trip. Go in the morning to escape the worst of the crowds.