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

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.

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
About the Author
By Rachel King
See full bioRight Arrow Button Icon

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
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • 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
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map

© 2025 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.


Most Popular

placeholder alt text
Law
Amazon is cutting checks to millions of customers as part of a $2.5 billion FTC settlement. Here's who qualifies and how to get paid
By Sydney LakeJanuary 6, 2026
2 days ago
placeholder alt text
Future of Work
AI layoffs are looking more and more like corporate fiction that's masking a darker reality, Oxford Economics suggests
By Nick LichtenbergJanuary 7, 2026
1 day ago
placeholder alt text
Economy
Mark Cuban on the $38 trillion national debt and the absurdity of U.S. healthcare: we wouldn't pay for potato chips like this
By Nick LichtenbergJanuary 6, 2026
2 days ago
placeholder alt text
Future of Work
'Employers are increasingly turning to degree and GPA' in hiring: Recruiters retreat from ‘talent is everywhere,’ double down on top colleges
By Jake AngeloJanuary 6, 2026
2 days ago
placeholder alt text
Success
Diary of a CEO founder says he hired someone with 'zero' work experience because she 'thanked the security guard by name' before the interview
By Emma BurleighJanuary 8, 2026
9 hours ago
placeholder alt text
Personal Finance
Current price of silver as of Wednesday, January 7, 2026
By Joseph HostetlerJanuary 7, 2026
1 day ago

Latest in Lifestyle

HealthHealth
America’s healthiest state has clean air and water, good education, and safe cities—And says a lot about the country’s rural-urban divide
By Tristan BoveJanuary 8, 2026
8 hours ago
LifestyleJensen Huang
Jensen Huang sports black leather jackets worth thousands of dollars — ‘It’s the revenge of the nerds’
By Sydney LakeJanuary 8, 2026
11 hours ago
Delta plane flying
North AmericaAir Travel
These are the 10 most on-time airlines in the world, and only one American company made the cut
By Jacqueline MunisJanuary 7, 2026
1 day ago
dokoupil
PoliticsMedia
‘Walter Cronkite would have never said something so self-serving’: CBS News’ new anchor Tony Dokoupil off to explosive start
By David Bauder and The Associated PressJanuary 7, 2026
1 day ago
Ted Sarandos
Successlifestyle
Netflix co-CEO says he doesn’t read business books—at all. Instead, he reads one 1902 fiction about a ship and its reckless ‘hot dog’ captain over and over again
By Preston ForeJanuary 7, 2026
1 day ago
Sarandos
Big TechM&A
‘Largest LBO in history’: Warner rejects Paramount again, scoffing at $87 billion worth of debt in its $108 billion bid
By Nick LichtenbergJanuary 7, 2026
2 days ago