George Town, Grand CaymanGeorge Town

Christopher Columbus sighted the Cayman Islands in May 1503, on his last voyage to the Americas, and named them Las Tortugas because the sea was full of turtles. Within a few decades mapmakers were calling them the Caymanas, after a word for the crocodile-like reptiles sailors believed lived there. There were no permanent inhabitants: the islands were a stop for ships that wanted fresh water, meat and turtles, and later a hiding place for privateers and pirates working the sea lanes between Jamaica, Cuba and Central America.

The English took Jamaica from Spain in 1655, and in 1670 the Treaty of Madrid recognised English rule over the Cayman Islands as well. Permanent settlement followed slowly. The first families are usually placed in the early to middle 1700s, and Bodden Town on the south coast is remembered as the oldest village. They came from Jamaica and elsewhere, and included the free, the enslaved and, by tradition, some sailors who stayed after leaving ships. The names of those families, Bodden, Ebanks, Watler, Parsons, Conolly, still fill the phone book and the street signs.

George Town, on the west coast, took its name later, in honour of the reigning British king. It grew because it sat beside the calm, sheltered water on the lee side of the island, where the mail boats and merchant vessels could anchor. For most of the 1800s it was a village around a courthouse, a few churches and a fort, not a town in the modern sense. The largest building in the district was the courthouse, which survives as part of the Cayman National Museum on Harbour Drive.

For nearly three centuries the islands were governed as a dependency of Jamaica. When Jamaica became independent in 1962, the Cayman Islands chose to stay under the Crown instead and became a separate British territory. They are now a British Overseas Territory with a locally elected Legislative Assembly and Cabinet, and a Governor appointed by the United Kingdom. The Legislative Assembly and the national heroes' memorials on Heroes Square in George Town are the visible parts of that system.

This history explains why the island feels both British and Caribbean at once: cricket and the King's Birthday parade, driving on the left, but fried fish, rum and heavy cake. It also explains why the past looks thin on the ground. Most early buildings were wood, and wood does not survive a Caribbean storm season for long.

Grand Cayman is flat, has no rivers and little farmable soil, so for most of its history people lived from the sea. The main early industry was turtling: catching green turtles on the reefs and offshore cays and selling the meat and shell to Jamaica and beyond. It was a hard trade, and it worked only while the turtles lasted. By the 1800s the local green turtle stocks around Grand Cayman had been fished nearly to nothing, and the turtlers had to sail hundreds of kilometres to the coast of Nicaragua to find them.

The turtle trade made Caymanians into sailors, and the shipbuilding, rope-making and trading that grew around it became the next industry. Caymanian schooners carried cargo around the Caribbean. From the early 1900s, and especially before the Second World War, many men worked as merchant seamen on ships based abroad and sent wages home. Families ran for months without their men, and a remittance economy grew up around them, which is one reason this small island has relations in Tampa, Honduras and Jamaica.

Slavery existed on the island and cannot be left out of the story. Emancipation in the British Caribbean took effect in 1834 and was followed by an apprenticeship period, and the island's own formal moves toward self-government began in the same generation. A historic house at Pedro St. James, near Savannah, is tied by local tradition to the first elected assembly of the islands in 1831, which is why it is sometimes called the birthplace of Cayman democracy. Check the site for its current interpretation before you visit.

The old economy left small traces you can still eat. Fish rundown, conch stew, turtle stew, cassava and heavy cake all come from a diet of sea catch, root crops and what a small island could grow. The turtle stew is now a contested dish, since turtle meat today comes from a farm at West Bay rather than the wild, and visitors disagree about whether to eat it. Most restaurants list it as a local dish, and it is fine to skip it.

The seafaring past also explains the old idea of the islands as a place outsiders passed by. Boats were the connection to the world until the middle of the last century. Regular commercial flights to Grand Cayman began only in the mid-twentieth century, and roads across the island took longer still. That isolation is the background for what happened next.

The waterfront of George Town is the oldest part of the town, and the smallest. Harbour Drive runs along the shoreline, Fort Street meets it at the ruined wall of Fort George, and the streets a block or two inland hold the Legislative Assembly, the library, banks and law firms. It is walkable end to end in ten minutes, and the walk tells you almost everything about the island's history: a fort, a courthouse, a square for public life, and a harbour where ships wait offshore.

Fort George was built in the 1790s, a period of naval war between Britain, France and Spain, when Spanish privateers could raid an island settlement in a night. It was a modest defence, with cannon on a low limestone wall. The fort was never tested by a large invasion, and by the twentieth century it had been used for other purposes and slowly lost its structure. What remains today is a short stretch of wall, a few features and an interpretive plaque, a ten-minute stop rather than a museum.

The museum a few minutes along Harbour Drive is in a building dating from the 1830s, which has served as a courthouse, a jail, a post office and government offices before becoming the national museum in the 1990s. Its collection is small and strongest on seafaring, turtling, the storms and everyday life before tourism. If you have time for one indoor stop on a hot or wet morning, it is this one.

There is no cruise dock in George Town. Big ships anchor offshore and bring passengers ashore by small boats called tenders to a terminal on the waterfront. On a day with three or four ships, several thousand people arrive within a couple of hours, and the harbour front, the shops and the boat operators reorganise around them. A pier project has been discussed for years; before you plan around a waterfront morning, ask your hotel whether the ships are in and whether the arrangement has changed.

The best way to use the waterfront is to arrive before 09:00, do the museum and fort, take in the square, and leave before the crowd gathers. If the ships are in and you want to avoid them, go to Camana Bay or the beach instead and return on a day when the harbour is empty.

In the 1950s Grand Cayman was poor and largely cut off, and the change came in two waves. The first was finance. In 1966 the islands passed the Banks and Trust Companies Law, which set up a licensing system for offshore banking and trusts. Combined with the absence of income tax, corporate tax and capital gains tax, it made the islands an attractive place to register funds, insurers and companies. George Town's business district, with its rows of law and accounting offices around Cricket Square and Elgin Avenue, is the result.

There is no income tax because the government pays for itself in other ways: import duties, fees for company registration, work-permit fees and stamp duties. This is why prices for goods on the island are high, and why a resort lunch costs what it does. It also explains the large expatriate workforce. About half of the people living on the islands are on work permits, from Jamaica, the Philippines, the United Kingdom, Canada, the United States and dozens of other countries.

The second wave was tourism. Seven Mile Beach, a long strip of white sand that is actually closer to eight or ten kilometres, was a swampy stretch of coast until developers began building hotels and condominiums in the 1960s and 1970s. The government kept the beach public up to the high-water mark, so even where a resort owns the land, the sand belongs to everybody. A dive industry grew alongside, because the reefs and the steep underwater wall on the north and west coasts are among the best in the Caribbean.

Camana Bay, a planned town centre near the north end of Seven Mile Beach, opened in 2007. It has a main street, a town square, offices, a cinema and a free observation tower, and its plan borrows from planned towns in the United States. Its market, restaurants and shops are the cleanest, most walkable public space on the island, and they show what a purpose-built place looks like next to the older, car-shaped George Town.

For a visitor, the two economies meet at the prices. A lunch of rice and beans at a local counter costs a fraction of a beach-club lunch, a taxi costs what a short flight costs elsewhere, and a bus ride is cheap. Knowing where the money comes from helps you understand where to spend it.

Grand Cayman lies in the Caribbean hurricane belt, and the calendar of the island still runs by it. The season is officially 1 June to 30 November, with the greatest danger from August to October. Locals date their lives by the big storms: Hurricane Gilbert in 1988, Hurricane Ivan in 2004, Hurricane Paloma in 2008, which struck the Sister Islands, and others that passed nearby.

Ivan is the one visitors hear about. It crossed the island in September 2004 at major-hurricane strength and pushed a storm surge across the low coast, flooding much of George Town and the west side. Most of the island's buildings were damaged and a large share were badly damaged. Power, water and telephones were out for weeks, the airport was closed, and many residents were evacuated. The recovery took years and was paid for by insurance, reserves and a large rebuilding programme.

The result is that much of what you see today is new. Buildings were rebuilt to stricter codes, with stronger roofs, shutters and setbacks from the shore. Resorts on Seven Mile Beach reopened in stages, and some renovated so completely that they are effectively different hotels. The pattern is worth knowing when you read an old guidebook: a landmark may have gone, and a new one taken its place.

For a traveller, the storm season is a planning problem, not a reason to stay away. Airlines and hotels have strong storm policies. Flexible fares, travel insurance with trip-interruption cover, and a hotel with a clear cancellation policy handle most of the risk. If a storm is forecast, follow the airline and hotel notices, leave early if told to, and do not go to the coast.

Between June and November you also see the calmer side of the season: fewer visitors, lower rates, hot weather, warm water and short heavy showers. Many locals like it. If you are flexible and fine with the risk, it is a legitimate time to visit.

The main reason people come to Grand Cayman is the sea. The island sits on top of a steep underwater slope, with shallow reefs close to shore that drop away into deep water within a short boat ride. This gives divers a wall dive on the west coast and snorkellers coral gardens within a swim of the beach. Visibility is often good and the water is warm all year.

The Cayman Islands were early in protecting this. The government set up a system of marine parks in 1986, which restricts fishing and anchoring in defined zones and bans the removal of coral. The Department of Environment enforces the rules and monitors the reefs. Local law also protects conch, lobster and turtles with seasons and size limits, which is why conch fritters and lobster are seasonal on the island, roughly November to April for conch, and why you should never take shells or coral home.

Stingray City began by accident. Fishermen used to clean their catch on a shallow sandbar in North Sound and southern stingrays learned to come to the boats for scraps. In the 1980s divers and tour operators began taking visitors there on purpose, and the site became one of the best-known animal encounters in the Caribbean. Today operators feed the rays squid under rules from the Department of Environment, and visitors stand in waist-deep water while the rays glide past. It is a managed encounter with wild animals, not a wild sea, and it works because of the rules. Follow the guide, do not grab or lift a ray, and shuffle your feet.

In 2011 the government sank a decommissioned navy ship, the Kittiwake, off Seven Mile Beach as an artificial reef. It sits upright in about 20 metres of water and is now covered in coral and sponges. It is a certified-diver dive and a good example of how the island turns a maintenance problem into an attraction.

On land the island has one animal that is worth knowing about: the Grand Cayman blue iguana, a rare species that nearly disappeared and has been bred and released by a conservation programme. Visitors can see some at the Queen Elizabeth II Botanic Park in North Side. Elsewhere, green iguanas, which are not native, roam the resorts.

A few things about how the island lives will make your visit easier. English is the language of daily life, with a Caymanian accent and some local words. People greet each other before any transaction, so begin any question in a shop, at a taxi rank or at a hotel desk with 'good morning' or 'good afternoon'. Locals use the word Caymankind for a friendly, helpful habit that the tourist board has adopted as a brand, and the habit is also real.

Local rules are strict and sometimes surprising. Wearing camouflage clothing is against the law for civilians. Drug laws are strict and include cannabis. Beachwear is for the beach, and a shirt and shorts or a cover-up is expected in George Town. Drive on the left, use roundabouts carefully and never drive after drinking; the police enforce it.

The island is orderly and clean, with few beggars, little litter and low crime against visitors. The principal risk is theft from cars, so lock valuables out of sight. The other real risks are the sun, the sea and the road: wear a hat and a rash vest, swim where locals swim, and take a taxi after drinks.

Food is a mix of Caribbean and international. The local dishes are fish and rice, fish rundown, conch stew and fritters, heavy cake made of cassava and coconut, and Tortuga rum cake. Restaurants add a service charge of 10 to 15 percent, so read the bill before tipping. Fresh conch and lobster are seasonal. Local beer is Caybrew, and the mudslide, a rum and coffee-liqueur drink, is tied by local lore to Rum Point.

The best way to see the island is with a mix of formats: a museum morning in George Town, a boat day, a beach day and a drive. If you rent a car, get a temporary local driving licence from the rental company, and plan around the two rush hours on West Bay Road. If you do not, taxis, a few bus rides and a tour or two will cover it. Whatever you choose, book Stingray City early and keep a spare day for the weather.