The rigging creaks and hums and crews trim sails as the boats dance across dazzling seas.
The green island provides a stunning backdrop.
Later, they'll be ashore, rum punch in hand, socializing with sailors from 30 countries.
It's Antigua Sailing Week -- one of the sport's most famous regattas with a reputation for spectacular racing and serious partying.
It began as a simple dash to Guadeloupe between friends in the 1950s, but this year's edition marks the 51st running of the prestigious week-long event.
Antigua narrowly escaped the wrath of Hurricane Irma, which devastated neighboring Barbuda last October, but the knock-on effects have meant numbers are down "by about 15-20 boats" compared with the bumper 145-boat entry for last year's 50th anniversary.
But organizers are still expecting to welcome about 120 boats and 1,000 sailors, who will bring about $4m of direct revenue to the island.
Sailing Week is based out of English Harbour, with its historic 18th century Nelson's Dockyard and stunning Antigua Yacht Club, on the island's south coast.
On the program is five days of coastal races of three to four hours, plus a longer race around Antigua race.
As the sun dips, the party starts. However, organizers are keen to insist the focus, once skewed too far towards the onshore activities, has been redressed.
"We've had our challenges, for sure," commercial director Alison Sly-Adams told CNN Sport. "The event lost sight a little bit of what it was all about and that's easy to do when you're in such a great destination.
"But it's absolute DNA is about fantastic racing and I think we've got the balance right."
In the past the regatta featured races ending at different beaches around Antigua, but the advent of more stripped-out racing boats, with deeper keels and fewer sailors living aboard, made the logistics of running the regatta more difficult.
Hence, it was brought back to English Harbour to restore its core values.
"What makes it so unique is we've got such a lovely backdrop and you get this great international atmosphere, but ultimately the reason people come is the racing," she adds.
"If you don't get that right and if you don't listen to the sailors and don't make sure they're getting what they need it's going to falter. That did happen for a while but I'm happy to say we've got the format right and the event seems to be building."
'Amazing cross section'
This year's fleet ranges from British businessman Sir Peter Harrison's 115ft ketch Sojana and superfast Volvo 70 Warrior to 20ft open keel boats.
About 40 per cent of boats are chartered by visitors for the week, 30 per cent are sailed across the Atlantic from Europe or down from the US, and 30 per cent are owned by Caribbean sailors.
The bulk of crews come from the UK, Germany, the US and the wider Caribbean region.
"We have an amazing cross section," says Sly-Adams.
"Yes, we have super rich yacht owners but there is a really good mix."
'Breaking down barriers'
In a further bid to democratize the event, Antigua established a national sailing academy in 2010 and introduced sailing into schools' national curriculum. In the early days, take up was slow, but it is now "absolutely bearing fruit," says Sly-Adams, with demand outstripping places available.
About 20 local youths will be sailing as part of the Youth to Keelboat Programme, with six pupils sailing a Cork 1720 against a crew of British youngsters from the state-run Greig City Academy in inner city London.
"The whole purpose was to break down the barriers," adds Sly-Adams.
"Yes, you've definitely still got that demographic of being a sport for white people, a sport for rich people but we're really seeing a lot of the youths getting into the sport and into the industry which is ultimately the goal -- to get them trained in sailing and confident so they're happy to go looking for jobs in the industry, of which there are many here."
The Greig Academy, in which 75% of children are officially under-privileged, made waves last year when a team of pupils competed in the famous Fastnet Race onboard a 45-foot yacht which they raised the funds to buy.
One of their number, 17-year-old Montel Fagan-Jordan, later earned the Yachting Journalists Association Young Sailor of the Year award, previously held by multiple Olympic medalist Ben Ainslie and Dame Ellen MacArthur.
"This project has snowballed from nothing," geography teacher Jon Holt told CNN Sport.
"It has become a massively aspirational thing where the youngest kids want to emulate Montel and all these others. Right now, we have this bizarre problem where we don't have the capacity to meet the demand."
Sailing Week comes at the end of a season which began with Antigua Charter Yacht Show in December, a superyacht regatta in January, the Caribbean 600 race in February and a classic yacht event earlier in April.
The income is "vital to tourism and the economy of Antigua and Barbuda," according to Charles Fernandez, Minister of Tourism and Economic Development, while aiding ongoing fundraising efforts for Barbuda and other islands such as Dominica to the south.
For the sailors, its salty reputation means it can be a "week-long marathon" for those pushing hard on and off the water.
But when the gun goes and sails are pulled in, thoughts of rum and reggae are buried until later.
"We've got this weird balance because in the Caribbean the whole perception is it will be very relaxed, which it is once you're off the water," says Sly-Adams.
"When you're on the water, it's really serious and very well run."