Michael Winner has coined a word for describing the time he’s spent on this, the most British of Caribbean islands, over the past quarter of a century: Barbadossing. For a fortunate few, the dilemma of who’s driving on New Year’s Eve and negotiating the chill winds of much of the British winter are cheerfully ducked and dived by heading to the second home on Barbados. The island has many charms: near-perfect weather, white sand beaches, several championship golf courses, plenty of direct flights from the UK and a level of infrastructure not easily matched throughout the rest of the Caribbean.

But there’s more to it than just sunshine, sand and a good safety record-the winter season in Barbados is made up of a string of glamorous events, from polo tournaments organised at one of the four grounds around the island (Prince Harry played this January) to the Barbados Gold Cup, a Flat race held at the Garrison Savannah Racecourse in Bridgetown since 1982. In between are cocktail parties, a jazz festival, gatherings held at the various houses that belong to the island’s national trust and, finally, the two-week-long performing-arts festival hosted by Wendy Kidd, mother to supermodel Jodie, at her house, Holders, which has been described as ‘a hybrid of Glyndebourne and Glastonbury’ by one regular.

Barbados has long been the winter destination of choice for the glitterati: the Barbados/London route was a regular scheduled flight for Concorde before she was decommissioned in 2003. Today, a string of film and television stars, businessmen and, more recently, Premier League footballers have made the island their second (or fourth) home. And a peppering of celebrity high-rolling glamour has inevitably followed in their wake: there is an outpost of the South Kensington Italian restaurant Daphne’s and the odd paparazzo is known to meet the flights at Bridgetown.

Despite this, however, the island has maintained a certain Caribbean cool-headedness that comes as a surprise for someone who expects to encounter thirty-something hedgefunders noisily swapping bonus-target anecdotes at the bar of an evening. Big chains have yet to descend and dominate: the hotel that retains its crown after 50-plus years of service remains the independently owned Sandy Lane and, after works to build the new Four Seasons stalled last year due to financial problems, there are none of the usual suspects of five-star international hotel brands on the island. Driving up the west coast-where house prices rival those of London’s Belgravia-you get a sense of how the balance has been retained as, in between driveways to multimillion- pound beachfront homes, are haphazardly built, slightly scruffy, candy-coloured clapboard chattel houses that are owned by Barbadians (Bajans in the local vernacular), whose rights to the land and the sea views they enjoy are protected by the government.

The island has an approximately triangular shape. The west coast, sometimes known as the Platinum Coast, is lapped by the calmer Caribbean and is the most desirable in terms of property; the eastern side of the island is more rugged in terrain, but the water is too dangerous for all but the strongest swimmers; the southern coast is less chichi, a tad more package touristy, but more authentically Caribbean some would say. Barbados west-coast house prices are routinely used as the benchmark for the most expensive in the Caribbean: prices on nearby St Lucia and Grenada are often 30% cheaper. ‘But houses with two-acre gardens on the west coast are as rare as some of the finest country houses in Gloucestershire,’ argues the Barbadian-born Dereck Foster of Bajan Services, the Knight Frank representative on the island. And it’s this rarity factor, added to the lively social scene and comparatively sophisticated lifestyle that maintains these prices even in the quietest of markets. ‘Although there have been fewer viewings in the past 18 months, the global downturn has meant that fewer developments have begun, so there’s less supply,’ says Andrew Mallalieu of Terra Caribbean. ‘That said, the majority of buyers on the west coast don’t care so much about making a profit-they just want somewhere beautiful to come from December to April.’

Other islands do try and give owners what Barbados does, but, inevitably, they can’t match up, explains Julian Cunningham of Knight Frank. ‘Owners spend four months at a time here; you don’t get the concentration of people living mid-to long-term on the other islands. People know they don’t get any nasty surprises here-it’s safe, it’s liquid and it’s accessible.’ Plus the island is only four hours behind the UK, so people still feel able to do business back in London. For those not wishing to be directly on the beach, several attractive estates have grown up inland, mostly around golf courses such as the Sandy Lane and the Royal Westmoreland.

The new kid on the block, however, is Apes Hill, a former sugar plantation on the second highest point of the island that is now a fantastic course, which meanders over the ridgeline to afford players views of both the Atlantic and Caribbean. Built around natural gullies and ravines, the 470-acre estate is home to the golfball-stealing Bajan green monkey and is being developed by Sir Charles ‘Cow’ Williams, a 70-something polo fanatic with an impregnable Bajan accent-at least to the untrained ear. Buyers can buy a plot and build their own home (from $500,000), purchase a house that’s already built (from $2 million) or get someone to build a house for them by investing in the turn-key option at Moonshine Ridge, where prices range from $3.5 million to $8 million. All owners are members of the country club and the polo ground-where tea, cakes and Pimm’s are served during match days-is on the doorstep. The plots of houses haven’t exactly been snapped up, but Linda Williams, head of sales and marketing, believes they are going to have a lively season this winter. ‘People are definitely back in the mood to spend money.’

Most agents agree the market has been somewhat sluggish over the past two years, but Barbados has fared better than many other islands, with average price falls from peak across the range of markets of 22%. Knight Frank had their strongest season last winter, which they attribute to buyers flying back to quality and core markets, ‘as well as the perception that some value had returned to the market,’ says Mr Cunningham. ‘In turbulent times, people want to see a place where things still get done and work goes on, and Barbados has that in spades,’ adds his colleague James Price.

‘This is most definitely a resale market- prices have become so competitive that there are prime-location high-end furnished properties offering better value than new-builds,’ believes Richard Eames of Island Villas, the Savills associate on the island. He cites Battaleys Mews, St Peters: the west-coast development has a three-bedroom town house with access to a clubhouse, swimming pools and tennis available for US$650,000. ‘That’s some 40% less than the original sales price.’

‘Buyer confidence has, understandably, been a little shaky in recent times-not helped by the fact that a number of projects failed to get off the ground or were delayed,’ adds Robert Green of Cluttons Resorts. The most public victim of the financial downturn has been the Four Seasons development, where the likes of Andrew Lloyd-Webber and Simon Cowell had bought houses, which ground to a halt last year. However, as this issue goes to press, work is beginning to restart on the development. Others are busy getting off the ground and drawing in inquiries from buyers, including the apartments on the beach at Beachlands in Holetown, and the new marina, Port Ferdinand, just north of Speightstown. ‘Certainly, unlike much of the rest of the Caribbean, Barbados hasn’t ground to a complete standstill,’ says Feona Gray of Caribbean Property International. ‘In a recession, people always go back to the core market-to what they know,’ adds Mr Foster. ‘And Barbados is the most solid destination in this part of the world with a strong resale market.’

NEED TO KNOW: An insider’s guide to Barbados

Visit Hunte’s Garden in St Joseph, where the entrance fee includes drinks (www.huntesgardensbarbados.com)

Party at the Oistins Fish Fry on Friday and Saturday nights and feast on local food: flying fish and macaroni pie

Sunday lunch at The Atlantis Hotel on the rugged east coast, where a special buffet tempts the island’s gourmets (www.atlantishotelbarbados.com)

Surf the Soup Bowl at Bathsheba, also on the east coast

Cocktails after walking the boardwalk on the south coast and watching the sunset at Tapas in Hastings

Supper overlooking the Caribbean Sea at Pisces in St Lawrence Gap, and at The Fish Pot, Little Good Harbour

Taste the Caribbean’s pirate past with 10-year-old Barbados rum at St Nicholas Abbey, a Jacobean plantation house

Listen to music at Holders House during the season (March 19-April 2, 2011), when COUNTRY LIFE’s own Kit Hesketh-Harvey takes the stage (www.holders.net)

Airport If your flight is delayed, visit the Concorde museum just next to the terminal and reminisce about the days of truly stylish international travel