Lounge area with tables and chairs and a pool table in a large open air hut
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Necker Island

Necker Island offers one of the Caribbean’s most stunning retreats. Here's our review of the private island resort.

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Bitter End Yacht Club Exterior view from ocean with all the buildings

Bitter End Yacht Club

This low-key resort on Virgin Gorda is known for its excellent sailing instruction and has been revamped after Hurricane Irma.

Eustatia Island

Eustatia Island, a 35-acre private island (available for full takeovers only) in the British Virgin Islands, is a low-key, friendly retreat that offers some of the finest barefoot luxury in the Caribbean. Read Indagare's review.
Bedroom at Guana Island, British Virgin Islands, Caribbean

Guana Island

Oddly enough, one of the Caribbean’s most private hideaways is just a ten-minute boat ride from Beef Island, home of the Tortola airport and the general hub of the BVI. But once you step onto Guana Island’s unassuming dock, thereis no mistaking that you have arrived at a truly special place—an 850-acre nature preserve and wildlife sanctuary dotted with only 20 whitewashed cottages. At most, only 35 guests at a time can enjoy the island’s unspoiled paradise, with seven virgin beaches, miles of tropical forests, hills and valleys, a salt pond and its resident flamingoes, and ruins of a sugar mill dating back to the 18th century. Guana is said to have the most diversity of flora and fauna known for an island of its size, and it serves as an annual summer field science station for visiting marine biologists from Harvard and Yale. There are 27 marked hiking trails so that guests can take in the wildlife themselves.

Aficionados of hippie-chic destinations such as Tulum and Mykonos will appreciate the resort’s casual ambiance and trappings. The rooms’ style was inspired by the island’s history as a sugarcane plantation owned by American Quakers, and this translates to dusty floral textiles and plenty of white wicker for a charming—if slightly dowdy—Nantucket effect. While some design choices are surprisingly off-target (a treadmill placed next to the bed in the bedroom of the otherwise stunning owner’s house, the three-bedroom Jost House Villa, comes to mind), for the most part the décor fits in the unpretentious, unfussy vibe. Conspicuously absent phones and televisions contribute to the rustic appeal, but WiFi across the island keeps guests from being completely disconnected. While there is no air-conditioning (except in the villas), the ocean breeze does the trick. In addition to 16 rooms in free-standing cottages—one of which comes with its own swimming pool—there are four villas, ranging from one to three bedrooms. The most unique accommodation is North Beach Villa, a one-bedroom oceanfront cottage on the island’s northern expanse with its own kitchenette, swimming pool carved out of coral, wrap-around porch and secluded stretch of beach. It feels like you’re on the very edge of the world, and I can’t imagine a more appealing haven for intimacy-seeking honeymooners or celebrities.

The service is genuine, ultra-accommodating and just as laissez-faire as you would expect. Guests help themselves to drinks during the day from an honor bar, and breakfast and lunch are served buffet-style. For dinner, there is a fixed menu (with a choice of two entrées) that changes nightly and, per Guana Island tradition, starts with soup such as conch chowder or West Indian pepper pot soup. Private dinners on the beach, in the lush Garden of Eden or on guests’ private porches can also be arranged. Though the region is notoriously food-challenged due to a lack of agriculture and commercial fishing, the excellent chef makes the most of local seafood and produce, including fruit from the resort’s on-site orchard. When I was driven down to this shaded oasis, its two gardeners whipped out their machetes and offered me slices of starfruit, papaya and wax apples from right off the plant.

Activities for the energetic include hiking to panoramic hilltops, playing tennis and partaking in the usual host of non-motorized water sports. However, most guests are in no hurry to move along, leaving the days to beachside lounging instead. One experience that shouldn’t be missed is Guana’s “Castaway Picnic,” in which guests are brought via boat to the deserted Bigelow Beach (accessed only by water) and dropped off with beach chairs, a picnic and a cell phone with which to eventually, reluctantly summon your boat ride back to civilization.

Oil Nut Bay Arial View of the property and ocean

Oil Nut Bay

Dreamt up by developer David V. Johnson, Oil Nut Bay is a real estate development and comprehensive marina on 400 acres of the North End of Virgin Gorda. Primarily focused on land sales and development, several of the private villas built on property are available within a rental program for visitors. With accommodations that range from one-bedroom suites to a six-bedroom beachfront villa, Oil Nut Bay is a great option for families and large groups.

The property also offers resort services for villa guests including a three restaurants and a coffee shop, three-level pool, watersports club, two tennis courts and a kids’ club. Picnics can also be prepared for guests to dine in nature with full set-ups at various “Picnic Destinations” around the property. Private chef services for in-villa dining, nanny services and spa services can all be arranged by the full-service concierge in the villas. The marina village has more than 90 slips offering access for boats up to 130 feet in length and marine services including an expert team, fully stocked market and boutique, plus the seafood-focused NOVA Restaurant (open for lunch and dinner).

Exterior view - Peter Island Resort at British Virgin Islands, Caribbean

Peter Island Resort

Although there are 52 rooms, Peter Island can often appear empty; guests tend to disappear into the island’s 1,800 acres. The original hotel, built in the 1960s, is divided into two parts. There are oceanfront rooms in A-frame buildings by the lobby and marina, and larger beachfront junior suites, a short walk from the main pool and restaurant, which should be booked as a first choice for the additional space and privacy they offer. Indagare tip: Request a room on the second floor for high ceilings and a sunny exposure.

For those who are traveling with children, the three villas are the ones to get. My personal favorite was Falcon’s Nest, offering six bedrooms and almost 22,000 square feet of unabashed luxury. Amenities include a full staff, infinity pool, media room, gym, nanny’s quarters and a van and driver for when guests want to descend from their hillside perch.

With five beaches at hand, most activities are water-focused, but there’s plenty more to do than dozing on the sand. Travelers can arrange a picnic lunch on the pristine and private White Bay Beach, paddle a sea kayak around Dead Man’s Bay, and work up a sweat at the resort’s gym and lighted tennis courts. Each night, a few guests are taken to watch the sunset from a remote hilltop with views of St. John and Norman’s Island. They are encouraged to settle into a colorful Adirondack chair with a bottle of Champagne before dinner.

Spa aficionados adore Peter Island’s sprawling facility for treatments. It features spacious rooms with private terraces overlooking the water, a serene pool, and a secluded hot tub nestled into the rocks near the spa’s own beautiful and windswept (but not swimmable) beach. Offerings range from classic massages and facials to Ayurvedic therapies designed to detoxify both mind and body. That the spa caters not only to resort guests, but also to the yachters who come onshore to experience its pampering, explains its 10,000-square-foot footprint.

As a private island getaway, it’s easy to lump Peter Island along with other castaway locales such as Tulum or Kamalame Cay. But with its prosaic design (dark wood, conservative prints, lots of stone) and rather formal main restaurant, Tradewinds, the property steers clear of any barefoot-hippie associations. Even the most relaxing of activities have a framework to them; for instance, guests can reserve Honeymoon Beach (maximum occupancy: 2 people) all to themselves ahead of time, but won’t stumble upon it by happy chance. While some may deem this lack of spontaneity restrictive, others will find it wonderfully liberating to hand over the reins and have someone else do the planning.

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Dock view from the water

Rosewood Little Dix Bay

While many of the BVI’s luxury resorts focus on honeymooners, Little Dix Bay is one of the most family-friendly resorts in the Caribbean.

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Pool at  Valley Trunk Estate, British Virgin Islands, Caribbean

Valley Trunk Estate

This family-owned compound, available for exclusive takeovers only, is located on a sprawling 19-acre estate on Virgin Gorda’s southern shoreline. For over 30 years, Valley Trunk has been the tropical getaway for the Wildensteins, who made their fortune as art dealers. Now, groups of up to 16 people can enjoy the villa as their own luxe home away from home.

The property’s grounds are spectacular, featuring lush gardens filled with bougainvillea, oversized cacti, mango trees and winding pathways leading to secret hammocks and small bridges. The main house, accommodations and lovely infinity pool are located at the top of a hill, allowing for first-rate ocean views. It’s a five-minute walk through the landscaped greenery (or a quick golf cart ride) down to the beach, where loungers and more hammocks await on the secluded 500-yard beach with alabaster sand, massive volcanic boulders like those at the Baths—which are just a quarter mile away. Those wanting to linger by the water will adore the oceanfront Bali House, a bamboo duplex pavilion that was deconstructed in its eponymous country, imported to the BVIs and rebuilt piece by piece by Balinese artisans brought in for the occasion. There’s no better spot for dinner al fresco.

Eight one-bedroom suites are spread out across multiple villas, making Valley Trunk ideal for multi-generational families or groups of friends traveling together. Though the rooms, which boast fabulous ocean views, are spacious and in impeccable shape—nothing feels tired or worn—the décor has not been updated in years and has a distinct retro vibe (shag carpeting, tiles with pastel patterns, et. al). Travelers seeking haute design or a sleek, modern feel should book elsewhere. Still, the attention to detail is thoroughly impressive, from Hermès placemats and toiletries to the stylish woven beach bags thoughtfully left in each bedroom closet.

With a house staff that’s been with the Wildensteins for over two decades, service is attentive and pampering, but never overbearing. The Valley Trunk team can orchestrate any and all activities, including paddle-boarding, kayaking, PADI dive instruction, massages and Ayurvedic spa treatments. (There is also a tennis court and small gym at guests’ disposal.) On my last night, they set up a grand bonfire on the beach, complete with Persian carpets laid over the sand and beanbag chairs from which to sip champagne. But really, the jewel in Valley Trunk’s island crown is Xanadu, the 68-foot yacht that is available for exploring the region’s coves accessible only by boat, snorkeling the excellent reefs, and touring the neighboring islands. (The use of the yacht is included in Valley Trunk’s rate, but fuel is an additional cost.) In the sailor’s paradise that is the BVIs, the ability to cruise at will all day before returning to the comforts of home is an unbeatable amenity.

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