Sometimes the most extraordinary journeys begin with the simplest premise: trade winter’s bite for turquoise waters and sunshine. My recent escape to the British Virgin Islands was about rediscovering what makes Caribbean luxury so eternally compelling. Three distinct properties, each offering a different interpretation of island sophistication, reminded me why the BVI continues to enchant even the most seasoned travelers.
The British Virgin Islands have long held a special place in the Caribbean constellation. Less developed than some neighbors and more refined than others, this archipelago of sixty pristine islands strikes a rare balance between accessibility and exclusivity. Direct flights into Tortola from San Juan and Miami, or a private boat transfer from St Thomas, make arrival effortless without tipping the destination into the mass market, while the intimate scale ensures you will never feel lost in a crowd.
Over several blissful days, I experienced a masterclass in Caribbean diversity. From Rosewood’s serene luxury to Oil Nut Bay’s contemporary glamour to Guana Island’s untamed old-world island vibe, each property revealed a different facet of what makes the BVI so magnetically appealing. Between sunset sails through Sir Francis Drake Channel, beach picnics on hidden cays, and evenings that seemed to stretch endlessly under star-scattered skies, it was impossible not to fall under the islands’ spell.
Here’s where I stayed, and what each one offered…
Rosewood Little Dix Bay
Mood: Timeless elegance. Understated luxury. Caribbean sophistication at its finest.
If there’s a property that embodies the soul of sophisticated Caribbean hospitality, it’s Rosewood Little Dix Bay. This legendary resort, originally conceived by Laurance Rockefeller in 1964, has been thoughtfully reimagined while preserving everything that made it iconic. The result is pure magic: a place where old-world grace meets contemporary comfort against one of the Caribbean’s most spectacular backdrops.
Pavilion-style accommodations are scattered throughout lush gardens and along a crescent of impossibly soft sand, each one positioned to capture cooling trade winds and stunning water views. The design philosophy here is “refined restraint.” No detail is overlooked, yet nothing feels overdone.
The clientele at Little Dix tends toward discerning travelers who appreciate subtlety over spectacle. Generations of families return year after year, drawn by the property’s commitment to gracious service and its ability to make luxury feel effortless. Days start with morning swims in crystalline waters, afternoons beneath swaying palms with a good book, evenings begin with cocktails as the sun melts into the Caribbean.
The Sugar Mill Restaurant showcases the island’s exceptional seafood with preparations that honor both local tradition and contemporary technique. Dining here feels like being invited to a friends dinner party, where conversation flows freely, the staff is all smiles, and I I may or may not have found myself singing a Caribbean rendition of The Gambler alongside Marcus, the ever-charming maître d’.
The Spa occupies a serene hillside setting with treatment pavilions that open to garden and sea views. Hiking up to the spa and being rewarded with the view and a dip in the infinity pool rewards, even before healing hands work their magic.
Our Favorite Memories: The dedicated butler service that miraculously and effortlessly appear and disappear just at the right moments. I just loved having them on my Whats App messenger with notes of the days activities and reminder of dining and spa times. Overall the entire team was genuinely happy to see us and just made us feel right at home, remembering our names, serving a planters punch, or just seeing what we were up to. I was quite taken by the care and comfort, but mostly of those SMILES! The property manages to feel both exclusive and welcoming—a delicate balance that few resorts achieve.
Oil Nut Bay
Mood: Contemporary glamour. Architectural drama. Modern luxury with Caribbean soul.
Just across the channel, Oil Nut Bay represents a completely different vision of Caribbean luxury. One that’s unabashedly contemporary and refreshingly bold. This newer property, developed with sustainability at its core, proves that environmental consciousness and sophisticated luxury aren’t mutually exclusive. The result is a resort that feels both cutting-edge and deeply rooted in place.
The architecture here is striking: angular villas and pavilions that seem to float above the landscape, floor-to-ceiling windows that frame panoramic views, infinity pools that blur the line between constructed and natural beauty. Villas range from 1 to 7 bedrooms with each more breathtaking and WOW than the next. Each accommodation is a private retreat designed for someone with impeccable taste and at least the appearance of unlimited resources, yet Oil Nut pricing is not out of reach.
The energy at Oil Nut Bay attracts a younger, more design-conscious crowd: successful entrepreneurs, creative professionals, wellness-seekers and families who appreciate innovation alongside tradition. The property buzzes with a subtle dynamism that’s infectious.
The Beach House and Nova restaurants are dining options for Oil Nut guests and the food is simply delicious but of course the island is blessed with multiple chefs who take care of villa guests for meals in their stunning homes on demand.
Activities Galore – A world class marina, racquet sports, enticing fitness facilities, an enviable kids club, a serene over-water spa, adorable boutiques, rescued horses, even flamingos – it’s all here.
Our Favorite Memories: I love the location of Oil Nut Bay and with their cadre of captained yachts, guests can jet set around the island for boozy lunches and dinners at local BVI hot spots such as Jost Van Dyke and Saba Rock. Also super fun to have a personal show-around with one of my favorite General Managers whom I have worked with at Secret Bay and Ambergris Cay and now at Oil Nut Bay. A great friend in hospitality makes all the difference for Resort to Laura Madrid’s client stays.
Always hard to say good-bye to such a perfect place, but alas, the research continues…
Guana Island
Mood: Untamed old-world Island elegance. Private sanctuary. Soul-stirring warmth.
If Little Dix represents refined tradition and Oil Nut Bay embodies contemporary innovation, then Guana Island offers something altogether different: the rare luxury of true privacy and untouched natural beauty. This 850-acre private island resort, home to just eighteen guest villas, feels less like a hotel and more like staying just where you were meant to be. The feeling is hard to explain, but if you measure to industry indicators – repeat guest ratio and very long average guest stays – that might just say it all. Guana is not fancy, it is real.
Guana Island operates on a simple principle: an exclusive hotel experience shouldn’t require compromising the natural world. The property is a working wildlife sanctuary, home to endangered species and pristine ecosystems. Your fellow guests include flamingos, iguanas, and countless bird species, all coexisting in remarkable harmony. It’s a place where you can snorkel over pristine reefs in the morning, hike countless trails to deserted beaches, and spot rare birds from your villa’s terrace in the evening.
The rustic but perfectly appointed accommodations embrace the island’s wild beauty rather than trying to tame it. Stone and timber villas are positioned to capture cooling breezes and spectacular views while minimizing environmental impact. There’s is air conditioning but we did not use it, the island trade winds cooled our room and rocked us to sleep each night.
The clientele at Guana tends toward those who consider privacy the ultimate luxury. Super yachts line up in the bay to enjoy the coveted position, but none are allowed to come on to Guana even to dine or use the spa – this is reserved for the privacy and use solely of Guana guests. Clearly this is a win for the repeat guests who treat the island like their own private retreat, returning annually for the same villa and the same slice of unspoiled paradise.
Hibiscus Spa – The tiny spa lies between the islands orchard and the beach, and my therapist delivered one of the most intuitive and relaxing massages I have had.
Dining at Guana
This is where Guana truly comes to life. Every meal is set up as a social gathering or dinner party with friends. Guests roll into breakfast at their leisure, often sharing a newspaper or a chat with others. Lunch is served as you wish at the main dining room or down at the beach, guests can dine alone or gather with their new friends. Cocktails and canapés start at 6:30pm and are quite the social gathering. There is a seating chart with each night your dinner companions being a new lot, and often in a different location. Guana likes to keep you guessing. Of course, tables are also set for just two and special requests are always welcomed. The cuisine here isn’t about culinary theatrics. It’s about exceptionally fresh seafood, vegetables from the island’s organic garden, and preparations that let natural flavors shine. Dining feels wonderfully communal, with conversations flowing between tables and new friendships forming naturally. The bar is always open and guests are encouraged to make their own drinks when they like, but there is always a barman nearby for those who like to leave the mixology to the pros.
The Nature Program sets Guana apart from any other Caribbean resort. Guided or independent hikes reveal hidden beaches, ancient petroglyphs, and bird-watching opportunities that rank among the Caribbean’s finest. The island’s dozens of hiking trails and seven beaches range from protected coves perfect for swimming to wild Atlantic-facing shores where crashing waves create nature’s most dramatic soundtrack.
Our Favorite Memories: Hiking to the island’s highest point at sunrise, where panoramic views revealed dozens of surrounding islands floating in seas of impossible blue. Discovering a completely deserted beach accessible only by hiking trail, where we spent an entire afternoon without seeing another soul. TIP: Bring real hiking shoes or boots, the trails are untamed.
One of the unexpected joys of our time at Guana was the people we met—each encounter a reminder of how travel brings together kindred spirits we might never have crossed paths with otherwise. There were the dynamic young professionals from Washington, a remarkably well-traveled couple from Richmond whose stories could fill a novel, and a duo of charming creatives from the West Village who kept us laughing. A tennis-loving British couple quickly became our court companions and island friends.
Guana has a way of expanding your circle in the most organic and heartfelt way. You arrive as strangers and leave with a richer collection of friendships and shared memories. And yes, there may have been a few tears when I hugged Samson goodbye, one of Guana’s most treasured souls and a true embodiment of its warmth.
Final Thoughts
I have travelled extensively near and far, and I have found that sometimes you can find perfection closer than you might know. This BVI trip was one that really allowed me to relax and replenish my soul with joy. BVI is not a one-and-done, I’ll surely return to island-hop again soon!
Ready to discover your own BVI paradise?
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