BVI 2026

May 30, 2026

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Back in 2017, we went down to the British Virgin Islands for a weeklong bareboat sailing charter, and heading back in January 2026 felt like visiting a familiar friend – one who’d been through a lot since we last met. Hurricane Irma changed plenty, but the soul of the BVI, especially out on the water, is exactly as we left it. Saba Rock is brand new, sure, but the rebuilt Soggy Dollar Bar and Hendo’s are still unmistakably themselves. And Willy T’s is always Willy T’s.

San Juan, Puerto Rico to BVI

Jeff, Jason, Joe and I started off by flying through San Juan, Puerto Rico – and the PR/BVI leg delivered right out of the gate. We knew it would be a small plane, but we didn’t expect to be the only passengers. While checking in, the gate agent looked up and said “if you guys are ready, the pilot is happy to leave early” – after a quick safety briefing, the four of us were wheels up.

“The One Eyed Cat”

When we arrived at the Moorings’ charter base that night, we were really excited to get on board, pour a drink, and settle in. Provisions (through Moorings) had already been delivered, and we quickly made the boat our home. This charter, we opted for a Leopard 42 sailing catamaran, and “The One Eyed Cat” was perfect: plenty of space, easy to handle, and an indoor/outdoor living configuration that worked perfectly for the week.

Norman Island / Willy T’s

First stop? Gotta be Willy T’s. One of my all-time favorite places, and the guys agreed – we ended up going twice: once in the afternoon (for our first Painkillers of the trip) and then again after a delicious dinner at Pirates Bight (for our night backflips). I’m not exaggerating when I say we met probably 50 people that night – that’s just what happens at Willy T’s…

The Baths / Spanish Town

Since a BVI trip can’t be all boat drinks, we stopped at The Baths for the swim-in workout and the full-loop hike. January temps make the whole thing pretty manageable, and we were back on the water before long. I’ll admit that anchoring in Spanish Town was more stressful than it needed to be since my timing was off. My killer crew stepped up, though, and even cooked up a great dinner while I fussed with anchor alarms, chart plotter track settings, and .

Saba Rock / Bitter End Yacht Club

Being back at a completely unrecognizable Saba Rock was surreal, but the post-Irma rebuild is something else. Dinner at Bitter End Yacht Club gave us the best outdoor table on the island – right up until a squall rolled through and reminded us who was really in charge.

Scrub Island / Marina Cay / Trellis Bay

Sailing straight from Saba Rock to Jost Van Dyke would have been a long push, so we broke it up with a night at Scrub Island – dinner and a dip in the pool. Fortunately we had an excuse to stop anyway: the boat had picked up a maintenance issue, and we swung by Trellis Bay to collect the Moorings engineer, who had everything sorted out in short order.

Sandy Cay / Jost Van Dyke

The leg from Scrub Island to Jost Van Dyke is one of my favorites – it’s as close to open-ocean sailing as you get in the BVIs, and with a mooring ball pre-booked, there’s no reason to hurry. We caught a solid breeze for a few hours, then dropped anchor off the beach at Sandy Cay for a swim and a cold beer on our own private island.

Once we reached Jost Van Dyke, we moored in Great Harbour and took the dinghy over to White Bay – obviously to hit up Soggy Dollar Bar and Hendo’s Hideout. Two of the BVI’s most iconic stops, and both are thriving. We also made it to Foxy’s before calling it a night. Now I get it.

Road Town

Before we knew it, our six nights were behind us, and it was time to return “The One Eyed Cat” to Moorings. The passage from JVD to Road Town is never the highlight, but it gave us a chance to take in the scenery while packing up our gear. We had one last night ahead and made the most of it – the highlight was playing darts late into the night at The Watering Hole with some of the nicest people we’d met all week. A fitting end.