Hi Reader,

Let me take you somewhere special today. Somewhere flat as a pancake, fringed uninterrupted pink sand beaches, rimmed in impossible shades of turquoise, and humming with that slow, sweet rhythm you only find far from the crowds.

Anegada.

A frequent question I get from BVI guests — crewed and bareboat alike — is: “Should we go to Anegada?” And my answer is almost always an unequivocal yes. It’s one of my favorite places in all of the Virgin Islands precisely because it feels so different. Anegada is wild, quiet, and spread out in a way no other BVI island is. It feels like slipping out the back door of the Caribbean and discovering your own private world.

But like all good adventures, there are caveats.

If the trade winds are pumping 15 knots or more — especially with any northerly component — the upwind slog can get bouncy and uncomfortable. And if you’re on a 5- or 6-day itinerary, Anegada does require you to give up time at other world-class anchorages. For a quick trip, I think it’s reasonable to skip. But if you can make room… trust me, the payoff is worth it.

So here’s how I’d spend a perfect day in Anegada — whether you’re settling in on a crewed yacht with everything taken care of for you, or you’re a bareboat skipper ready for a little island adventuring at your own pace.

Morning: The sail from North Sound and settling into island time

If you push off the mooring in North Sound around 8:00 AM, you’ll usually ride a fresh breeze up to Setting Point and be on the ball by 10:00 or 10:30. It’s a beautiful run — open water, a low sliver of land growing on the horizon, and often a small parade of boats heading the same way. This is also a great time to drag some lines for solid chances at landing mahi or tuna.

Crewed guests, your captain will already be coordinating logistics behind the scenes — transportation plans, dinner orders, and any special experiences you want that day. Bareboaters: the first housekeeping item is choosing your dinner spot and putting in your lobster order. Potter’s, Wonky Dog, Lobster Trap, and Anegada Reef Hotel all do phenomenal beach-grilled lobster and fresh-caught fish.

Once you’re settled, grab your day bag — towels, water, snorkel gear, sunscreen — and step onto one of the Caribbean’s most barefoot-friendly islands.

Exploring the North Shore: Wild beaches and barefoot bliss

The island is easy to navigate. No map required. Hop in your preferred mode of transportation - moke, jeep, or truck, point yourself east and wander.

Stop 1: Flash of Beauty — a snorkeler’s dream

Your first destination is Flash of Beauty, which I still think has some of the best off-beach snorkeling in the BVIs. On the way, keep an eye out at the Flamingo Pond overlook — if the timing’s right, you’ll see flashes of pink sweeping across the water.

Slip into the sea at Flash of Beauty and you’ll find healthy corals and a healthy amount of marine life. Afterwards, grab a roti from Monica or wander next door to Big Bamboo on Loblolly Bay for lunch. Both spots are classic Anegada: breezy, unpolished, and full of character.

Stop 2: Anegada Beach Club

As you work your way back west, make a stop at Anegada Beach Club. Even if you’re not staying in one of their iconic tented cabanas, the pool, the vibe, and the lobster pizza — yes, lobster pizza — are worth the detour. They also run a free shuttle from Lobster Trap if you ever want to return another time.

Afternoon: Cow Wreck, lagoon waters & slow living

Eventually you’ll wind up at one of my favorite beaches in all of the BVIs: Cow Wreck Beach.

This stretch of shoreline looks like someone turned the saturation dial all the way up — glowing turquoise shallows, powdery white sand, and that peaceful lagoon-style swimming that keeps you anchored in waist-deep water for far longer than you intended.

Settle in at TIPSY by Ann for a cold rum drink, a few hours of swimming, and that special kind of stillness that Anegada does so well. It’s the definition of a perfect Caribbean afternoon.

Evening: Sunset rituals and lobster under the stars

Head back to the yacht for a rinse, slip into your breeziest resort wear, and enjoy a Captain's sundowner while the sky turns peach and gold over Setting Point.

Dinner on Anegada is always a moment. That beachside grill, the crackle of lobster shells over the fire, tables lit by lanterns, toes in the sand — it’s simple, but unforgettable. A perfect punctuation mark on a perfect day.

Optional highlight: A Horseshoe Reef adventure

If an extra day in Anegada, or are interested in some sea-based exploration, arrange a trip out to Horseshoe Reef, the fourth-largest barrier reef system in the world. Your crew may be able to take you out on the tender if it’s large enough; otherwise, local guides like Kelly run excellent tours.

The highlights here are pure magic:

• A drift snorkel over thriving coral and swirling marine life
• The surreal white mountains of Conch Island​
• Crystal-clear cuts through the reef that feel almost otherworldly

For ocean lovers, this is one of the great natural wonders of the BVIs.

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If you’re still wondering whether Anegada is worth building into your itinerary, the answer is yes — as long as the weather cooperates and you have the time. It’s different from the rest of the BVI in all the right ways, and that’s what makes it such a rewarding stop.

That's it for today! - Matt Weidert