• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Trendingnow

1

The millennial generation is split in 2: an older crowd with boomer-style comfort, a younger set going 'back to the early 1900s'

2

Trump pulls back after Iran crosses his red line as U.S. military breaks two-week streak of airstrikes amid talks for potential Hormuz deal

3

'The demographic dividend of the last 40 years is ending': J.P. Morgan says the world is running out of the two things that kept interest rates down

1

The millennial generation is split in 2: an older crowd with boomer-style comfort, a younger set going 'back to the early 1900s'

2

Trump pulls back after Iran crosses his red line as U.S. military breaks two-week streak of airstrikes amid talks for potential Hormuz deal

3

'The demographic dividend of the last 40 years is ending': J.P. Morgan says the world is running out of the two things that kept interest rates down
LifestyleInside Look

Inside this luxurious Caribbean hidden gem ahead of its 60th anniversary

By
Rachel King
Rachel King
Down Arrow Button Icon
By
Rachel King
Rachel King
Down Arrow Button Icon
October 28, 2023, 12:00 AM ET
And getting to the British Virgin Islands is about to be easier than ever with a new route via Tradewind Aviation.
And getting to the British Virgin Islands is about to be easier than ever with a new route via Tradewind Aviation.Courtesy of Rosewood Little Dix Bay
Add Fortune on Google for similar content.

Situated around a crescent beachfront in front of the gemstone-like hues of the Caribbean sea, Rosewood Little Dix Bay could be considered a hidden gem in the British Virgin Islands. But really, the resort is something of a landmark after nearly 60 years in operation.

Recommended Video
The Rosewood Little Dix Bay resort, as seen from the dock.
Courtesy of Rosewood Little Dix Bay

Founded in 1964 by American financier and conservationist Laurance Rockefeller (yes, of those Rockefellers), Rosewood Hotels has owned the Little Dix Bay resort property since the early 1990s. The 500-acre property completed a four-year renovation in early 2020 after closing for a partial refurbishment in 2016 before being entirely shuttered in the aftermath of Hurricane Irma in 2017.

Inside the Great Room and reception hall.
Courtesy of Rosewood Little Dix Bay

Little Dix Bay offers 81 accommodations, consisting of 42 guestrooms, 35 suites, two beach houses and two hillside villas. Based on the designs of luxury architecture firm OBMI and New York-based design team Meyer Davis, the most prominent upgrades can be seen in the modernization of the suites and dockside as well as the new Reef House restaurant. Overall, the property’s blend of sophisticated Caribbean sensibility with mid-century modern design is meant to evoke a relaxed yet refined sense of luxury bolstered by the surrounding natural beauty.

A villa bedroom at Rosewood Little Dix Bay.
Courtesy of Rosewood Little Dix Bay

Central to that is the restaurant’s food and dining program. Reef House, the resort’s colorfully designed signature restaurant, showcases premier al fresco “farm-to-fork” dining for lunch and dinner, with fresh provisions and ingredients sourced daily from the property’s on-site garden as well as through local purveyors.

The Rum Room bar at Pavilion restaurant.
Courtesy of Rosewood Little Dix Bay

Rosewood Little Dix Bay recently announced the appointment of new executive chef Andy Gaskin, who will oversee the resort’s four restaurants and bars, which along with Reef House include Pavilion (open early in the morning for full service breakfast), Sugar Mill (open for dinner and serving tapas-style dishes with an island influence), and Rum Room, a craft cocktail bar that has 107 different labels of aged and rare rums in its collection. All of the restaurants are open air, but keep the guests well protected from the fierce sunshine and any unexpected rain.

Reef Bar, open for lunch and dinner, overlooking Little Dix Bay.
Courtesy of Rosewood Little Dix Bay

The resort also offers a range of activities including water sports (such as snorkeling and kayaking), sailing lessons, and plenty of onsite fitness options with the fully equipped gym, six tennis courts, and two pickleball courts with the option to book private lessons with an instructor. Offsite, guests can book private tours to exploring the local baths of Virgin Gorda as well as curated “beach drops” to one of the seven secluded beaches on Virgin Gorda accessible via boat. For the day, guests can have their own personal and private beach day with a picnic lunch and enjoy an afternoon of sunbathing, swimming, and snorkeling.

The fitness center is open 24 hours daily.
Courtesy of Rosewood Little Dix Bay

For a more adventurous beach day, guests can tour the “wilderness beach,” dubbed as such by founder Laurance Rockefeller. In a guided tour, guests can partake in a Snorkeling Safari where they will bear witness to the incredible sea life native to the destination. Also there is an exploration of the area’s wildlife, where guests are invited on a scavenger hunt throughout the island to find different species of animals and flora, and a hike on the property’s grounds to experience sea life and fish. 

The pickleball courts at Rosewood Little Dix Bay.
Courtesy of Rosewood Little Dix Bay

For a more relaxing experience, Sense, A Rosewood Spa, is perched high on a hilltop with the best views in the area, which spa goers can enjoy from private plunge pools while sipping on herbal teas. But the spa here also offers an offsite excursion: the “Journey to the Baths” package is a unique wellness offering in which guests can explore the healing waters of British Virgin Islands in a national park, followed by a body or face spa treatment back at the hotel.

The ensuite bathroom in a two-bedroom suite.
Courtesy of Rosewood Little Dix Bay

Rates at the Rosewood Little Dix Bay start at $1,125 per night for an ocean view cottage with a private patio. Low season coincides with hurricane season, which should be wrapping up by November, and the property is gearing up for a busy holiday season starting in December.

An infinity pool and terrace attached to one of the villas.
Courtesy of Rosewood Little Dix Bay

Reaching the British Virgin Islands does take some planning, either by air or sea, although it is soon about to be easier than ever. Tradewind Aviation, a U.S.-based aircraft operator that provides both scheduled and private charter service in the Caribbean as well as New England, is expanding its service with a new route between San Juan International Airport in Puerto Rico to Virgin Gorda in the British Virgin Islands. And while the airfield at Virgin Gorda is quite small, the huge benefit is that it is less than a five-minute drive from the Rosewood property.

Tradewind recently invested in expanding its aircraft fleet with the acquisition of 20 new PC-12 NGX pressurized, single-engine airplanes, which will be delivered over the next five years. Having pressurized cabins is a big selling point for Tradewind as many other shuttle airplanes in the Caribbean, including to the British Virgin Islands, are not pressurized, resulting in hotter cabins and restrictions on how high the aircraft can fly, which is a sticking point when it comes to flying in inclement weather. 

A Tradewind Aviation plane takes off over St. Barths in the Caribbean.
Dylan Diaz for Tradewind Aviation

Tradewind’s scheduled service to St. Barths is available year-round from San Juan and Antigua. Additionally, from December 2023 to April 2024, Tradewind’s scheduled service to Anguilla will return with flights departing from San Juan.

The Virgin Gorda launch follows Tradewind’s expansion in September into the southeastern United States with the opening of a new aircraft base near Palm Beach, Florida, continuing its growth plans for 2023 and beyond. Tradewind says its opening of a Florida base is reflective of the continued rise in demand for private charter services.

About the Author
By Rachel King
See full bioRight Arrow Button Icon
Add Fortune on Google for similar content.

Latest in Lifestyle

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • TikTok icon
  • YouTube icon

Latest in Lifestyle

Why lotteries can make winning feel more valuable than buying
Arts & EntertainmentBusiness
Why lotteries can make winning feel more valuable than buying
By Tatiana SatauaJuly 26, 2026
2 hours ago
g
SuccessCrime
Gen Z ‘teen takeovers’ go from hijinks to shootings, theft and vandalism. Blame ‘adolescent brain development’
By Safiyah Riddle, Corey Williams and The Associated PressJuly 25, 2026
22 hours ago
A Hims cofounder fired his entire marketing team for AI. Now his 24/7 online vet service is growing 20% a month
SuccessMarketing
A Hims cofounder fired his entire marketing team for AI. Now his 24/7 online vet service is growing 20% a month
By Sydney LakeJuly 25, 2026
22 hours ago
Roderick Wong, MD is Managing Partner and Chief Investment Officer of RTW Investments
Commentary250 Years of Innovation
When 10,000 doctors stood up and cheered for a cancer drug — America’s innovation machine made it possible
By Roderick WongJuly 25, 2026
1 day ago
m
Commentarydisruption
The Messi Test and how the Spaniards messed with it: what the World Cup final taught me about the jobs AI can’t touch
By Bhaskar ChakravortiJuly 25, 2026
1 day ago
What it’s like to be a founder of the most high-stakes startup ever, OpenAI
AIOpenAI
What it’s like to be a founder of the most high-stakes startup ever, OpenAI
By Alyson ShontellJuly 25, 2026
1 day ago

Most Popular

The millennial generation is split in 2: an older crowd with boomer-style comfort, a younger set going 'back to the early 1900s'
Real Estate
The millennial generation is split in 2: an older crowd with boomer-style comfort, a younger set going 'back to the early 1900s'
By Nick LichtenbergJuly 25, 2026
1 day ago
Trump pulls back after Iran crosses his red line as U.S. military breaks two-week streak of airstrikes amid talks for potential Hormuz deal
Middle East
Trump pulls back after Iran crosses his red line as U.S. military breaks two-week streak of airstrikes amid talks for potential Hormuz deal
By Jason MaJuly 25, 2026
16 hours ago
'The demographic dividend of the last 40 years is ending': J.P. Morgan says the world is running out of the two things that kept interest rates down
Economy
'The demographic dividend of the last 40 years is ending': J.P. Morgan says the world is running out of the two things that kept interest rates down
By Eleanor PringleJuly 24, 2026
2 days ago
An 11-year-old is cleaning his neighbors' trash cans for $10 each—he now has 100K followers as teens face the worst summer job market since 1948
Success
An 11-year-old is cleaning his neighbors' trash cans for $10 each—he now has 100K followers as teens face the worst summer job market since 1948
By Orianna Rosa RoyleJuly 25, 2026
1 day ago
Jensen Huang made his $172 billion fortune on AI chips. His family's $75 million gift to Vanderbilt argues art decides what technology is for
Big Tech
Jensen Huang made his $172 billion fortune on AI chips. His family's $75 million gift to Vanderbilt argues art decides what technology is for
By Sydney LakeJuly 23, 2026
3 days ago
Startups are installing tiny data centers in people’s homes to reduce strain on the beleaguered electrical grid
Environment
Startups are installing tiny data centers in people’s homes to reduce strain on the beleaguered electrical grid
By Sasha RogelbergJuly 25, 2026
23 hours ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.