Hi Reader,

If you’ve followed Yacht Warriors for a while, you probably already know how much I love Anegada. I’ve written before about how I’d spend the perfect day there.

But eventually, you have to leave. And when we do, Jost Van Dyke is typically where we head next.

If I were planning your crewed yacht charter, here’s exactly how I’d spend the next 24 hours.

The Sail Back from Anegada

After breakfast, you’ll make the long, easy sail from Anegada back toward Jost. This is one of my favorite sails of the week. After spending much of the trip working your way north and east, you finally get to turn around and let the trade winds do most of the work. It’s a great morning to settle in, enjoy the ride, and let your captain worry about the sailing.

And if you’re into fishing, get the lines out. This is one of my favorite days to troll in the BVI. I’ve caught mahi on this run several times, and you’ve also got a chance at tuna or, when they’re around, wahoo. There’s nothing quite like hearing the reel start screaming in the middle of an otherwise relaxing sail—and if you get lucky, your chef might have some very fresh ingredients to work with later that day.

First Stop: Sandy Spit

You’ll typically arrive around lunchtime, but rather than heading straight to where you’re spending the night, I’d stop at Sandy Spit first.

Sandy Spit is exactly what it sounds like: a tiny spit of sand with a few palm trees surrounded by beautiful Caribbean water. There’s not much there, which is part of the appeal. Go ashore, swim, throw the football around if you brought one, or just enjoy having this little patch of paradise mostly to yourself.

Then I’d head back to the yacht for lunch. You’ll have a beautiful view across the channel toward Tortola, and it’s a great place to spend an hour or two before moving on.

Where to Spend the Night: Diamond Cay Over Great Harbour

From there, I’d head over to Diamond Cay for the night. This is one place where my recommendation is probably a little different from the standard BVI itinerary.

Most people will tell you to stay in Great Harbour. Personally, it’s just not one of my favorite anchorages in the BVI. It’s usually crowded, the mooring balls are packed pretty tightly together, and you’ve got ferries coming and going throughout the day.

That doesn’t mean you shouldn’t go. If Foxy’s is on your list—and for a lot of first-time visitors it is—Great Harbour might make perfect sense. Foxy’s is an iconic BVI stop and absolutely worth experiencing.

But if it were my trip, I’d stay at Diamond Cay.

Diamond Cay is much quieter, the setting is beautiful, and you still have plenty to do. B-Line Beach Bar is one of my favorite little spots in the area. It’s rustic, laid-back, and a fun place to grab a drink and play a game of cornhole. You’ve also got Foxy’s Taboo nearby if you want to stop in for another drink or something to eat.

The Bubbly Pool

The other reason I like staying here is the Bubbly Pool.

If you’ve never been, the Bubbly Pool is a natural pool on the Atlantic side of Little Jost Van Dyke. When the swell is running, waves funnel through a narrow opening in the rocks and rush into the pool, creating what feels like a natural jacuzzi. It’s a short walk over from the Foxy’s Taboo area and definitely worth doing if the conditions are right.

That’s the important part: it depends on the swell. If it’s been dead calm, you’re not going to get the full effect. Your crew will know what the conditions are doing and whether it’s worth heading over.

After that, I’d head back to the yacht, have dinner aboard, and enjoy the evening at Diamond Cay.

Sunrise at White Bay

The next morning is where having a crew really pays off.

I’d have your captain get going early and move the yacht around to White Bay. You don’t have to worry about any of it. By the time you’re ready for breakfast, you’re sitting in one of the best spots in White Bay with the Soggy Dollar right in front of you.

I think early morning is by far the best way to experience White Bay. Later in the day, the beach gets busy with day-trippers and boats coming and going. In the morning, it’s a completely different place. The beach is quieter, the water is beautiful, and you can actually slow down and enjoy it before things get going.

Breakfast, a Painkiller, and No Rush

Have breakfast aboard, go for a swim, and eventually make your way ashore for a Painkiller at the Soggy Dollar. Yes, it’s touristy. But the Painkiller was invented here, and I don’t think you can come all the way to Jost Van Dyke without having at least one.

For lunch, you’ve got two good options. I’d be perfectly happy staying aboard and having your chef prepare lunch while you enjoy White Bay from the yacht. But if you want to eat ashore, my favorite spot on the beach is Hendo’s Hideout.

After lunch, don’t be in a hurry to leave. Spend another couple hours on the beach, swim, have another Painkiller, and enjoy it. One mistake I see people make with BVI itineraries is trying to fit too much into every day. You’ve spent a lot of money and traveled a long way to be here. You don’t need to turn your vacation into a checklist.

Next Stop: Norman Island

Sometime in the early afternoon, I’d have your captain pull the hook and start making your way toward Norman Island. That’s typically my next stop and puts you in a great position for another full day of exploring, with The Caves, The Indians, and the Willy T all nearby.

But we’ll save Norman Island for the next one.

For me, the perfect 24 hours on Jost isn’t about trying to hit every beach bar on the island. It’s lunch at Sandy Spit, an afternoon and evening tucked into Diamond Cay, and then getting to White Bay early enough to enjoy it before the crowds arrive.

That’s how I’d do it.

Have a great week!