In March 2026, nine of us spent six nights bareboat chartering a 50-foot power catamaran through the British Virgin Islands with a captain aboard, then two more nights in St. John.
The trip, at a glance
- Crew: nine total, four couples and one single
- Boat: Unwinding, a 50-foot Aventura power catamaran, part of the Virgin Charter Yachts fleet, booked through Virgin Island Sailing
- Booked: about thirteen months out
- Getting there:
- First four: flew in the afternoon before, one night at Buoy Haus, 10 a.m. ferry to Tortola, cab to Nanny Cay arranged by Virgin Island Sailing, checked and topped off provisions, off the dock within an hour or two
- Other five: direct flight from Boston on departure day, car service to Red Hook, Chillout Charters through customs in about ten minutes
- Provisioning: through RiteWay, Steakation Butchers, Caribbean Cellars, and Island Surf and Sail (specifics below)
With Unwinding checked in and stocked, the first four left Nanny Cay with Lefty, our captain for the week, and cruised around to West End, where the Chillout Charters boat and Unwinding came together in the middle of the harbor and the other five climbed aboard. From there, it was straight to Norman Island.
Norman Island, the first night
We picked up a mooring in the Bight, had a quick lunch after a long day of travel, and then went straight to Willy T (the William Thornton), the floating bar that’s been anchored there in one form or another for decades. Hours there, dinner and some cocktails back on the boat, and a couple of us went back for a last round, Lefty giving them a ride over, which was probably a good idea given the condition they were in by then. Not a bad way to start a week.
Cooper Island, a whole day of doing very little
We moved to Cooper first thing and didn’t leave. Lunch at the Cooper Island Beach Club, cocktails standing in waist-deep water, and a long stretch of floating on a water hammock from Island Surf and Sail, quite possibly the single best piece of gear we rented all week.
At some point, before or after dinner, memory’s fuzzy on that detail, we hiked up to a lookout at the top of the hill for the view over the anchorage.
The Rum Bar in the evening, dinner on the boat, and one of the quietest, best nights of the trip.
The Baths, a swim-in stop
From Cooper Island we headed straight to The Baths. Three of the group were first-timers, and The Baths wasn’t a stop we were skipping. We picked up a mooring, and for the first time swam in rather than taking the dinghy the whole way, Lefty ran us up to the dinghy line and we covered the rest ourselves. Cruise ship passengers had one section of the path backed up into a real bottleneck, no way around it but to wait it out. Otherwise a relatively quick pass through, then a swim back out to meet Lefty for the ride to North Sound.
The Baths and North Sound
Leverick Bay turned into a longer stop than planned. The second night there, one cabin’s air conditioning went out. Someone came out to fix it, a few hours’ work, time we used to finally get to Hog Heaven (Virgin Gorda) for lunch on the ridge above North Sound, one of the best views in the islands, then back to Leverick for a round of drinks. Nobody’s week was ruined over it, just the one real hiccup of the trip.
From there, a mooring outside Bitter End. We spent a few hours there, standing in the water, and drinking at the Reef Sampler, Bitter End’s beach bar, which used to be a 1970s workboat before Hurricane Irma sank it in the Sound. Bitter End raised it off the seabed, refit it, and put it back to work as a bar.
After Bitter End, the Rum Runner, the little boat that circles North Sound with frozen drinks, came by. We had a round of Rum Runners. Drake wasn’t out on the boat that day, but we got to meet Sandy for the first time. Showers, then over to Saba Rock, where we caught a beautiful sunset, for what turned into apps that were really dinner.
Anegada, a truck and a lot of open water
We were moving by seven-thirty for the crossing to Anegada, about an hour from North Sound.
We rented a truck and Lefty drove. Straight to Anegada Beach Club for the pool and lunch, then over to Cow Wreck Beach, empty when we got there, and down the sand to Tipsy by Ann, which was a lot livelier. Truck back to the harbor, a round at the Lobster Trap, and back to the boat for dinner and yet another beautiful sunset. Anegada doesn’t feel like the rest of the BVI. Flat, coral, wide open water on every side. It’s worth the crossing if conditions and time allow.
The Dogs, Guana Island, and a barbecue on Jost
From Anegada we headed straight for The Dogs for a quick snorkel, then over to Guana Island. We normally stop at Monkey Point here for snorkeling, but this time Lefty had us go a little further into the bay, to the end of White Bay, for something more relaxed. We made great use of the water hammock floating off the back of the boat, paddled in, and floated for a couple of hours doing nothing in particular. A brief passing shower came through at one point, not enough to even get us out of the water.
Mid-afternoon we tried Great Harbour first, but no moorings were available, so we moved on to Little Harbour, a first for most of the group this trip and a little lower-key than Great Harbor. We put in a reservation at Sidney’s Peace and Love for the barbecue and lobster. Back to the boat to clean up and hang out on the flybridge, which has its own wet bar and enough room for all nine of us at once, before heading back in for dinner.
That’s where we met the crew of the Wandering Hillbilly, out breaking in a new boat this season.
White Bay
We pulled out of Little Harbour just after 6:30 a.m. and were in White Bay by 6:45, second row rather than first, but close enough to swim in easily. The early arrival meant time to slow down, breakfast on the boat looking out over a quiet, empty White Bay with a rainbow overhead, then still plenty of time to swim in and walk the beach while it was empty, before it filled in fast, and it did fill in fast.
We spent the day working through the regulars, Soggy Dollar, Hendo’s, Gertrude’s, before an evening cruise to Soper’s Hole for dinner at Pusser’s, packing up for an early departure the next morning.
Handing back the boat
Early the next morning we caught the first ferry from the customs dock at Soper’s Hole to St. John while Lefty took Unwinding back to Nanny Cay. Six nights aboard, done. One person split off before breakfast for a flight home, which left eight of us, four couples, for the St. John half of the trip.
Breakfast at HiTide, which has become a tradition at this point. Our rooms at the Flamingo House weren’t ready, so we checked our bags and spent a few hours at Maho Bay instead. Back by taxi, pool time at The Saint, and an evening that turned into an apps crawl rather than a sit-down dinner, drinks at the upstairs bar at Ocean 362 in Gallows Point, another round at the Longboard, and a last stop at the Beach Bar.
Four more of the group flew out the next day, down to four of us for one more night. We spent it at The Saint’s pool, drinks at the Blind Donkey, dinner at Karma, and more bar hopping after, the Beach Bar again, then Woody’s.
The last morning was a ferry to St. Thomas, a pickup from Jermaine Petty’s Mr. Reliable car service, and lines at the airport longer than any we’ve seen there on past trips. The red cap service was worth every dollar. The terminal was packed and barely air conditioned, but we made the flight, direct back to Boston. We saw the kids before they went to bed that night, and they’re still asking when we’re taking them.
Why we still wanted a captain
Nine of us, one boat, and Lefty at the helm the whole week, worth saying plainly, it made the trip. He found us a spot just off the end of White Bay Beach on Guana Island we never would have known to look for any, and got us a perfect anchor spot in front of Soggy Dollar on Jost Van Dyke, which fills in fast and isn’t easy to get without someone who knows the timing. Virgin Charter Yachts doesn’t allow bareboats to anchor there on their own either, a captain aboard is required, a policy plenty of other charter companies share.
He drove us around Anegada in the rental truck. On the days we were off swimming, snorkeling, or camped out at a beach bar, he stayed with the boat, so none of us had to think about it. At White Bay in particular he stayed aboard all day to keep an eye on things, that anchorage can turn into something close to bumper boats, there are videos online of unoccupied boats drifting off their moorings into everything around them.
At the end of the week he dropped us at West End and took Unwinding back to Nanny Cay on his own, which meant we walked straight onto the ferry to St. John instead of losing half a day getting the boat home ourselves. Bareboat is the cheaper way to charter, but bareboat with a captain did a lot of the work a fully crewed trip does, minus the cooking. Ultimately, Lefty took on all the responsibility for the boat, and given how some of these trips can go, that’s not something we take for granted.
What we thought of the boat
A few thoughts on the boat itself. Unwinding was brand new, less than a year old. The layout was tremendous, six cabins. The two rear cabins run smaller, Lefty took one, our single took the other. The communal spaces were impressive. We used every one of them, the aft deck, the salon, the flybridge, the bow. This boat would be perfect for an add-on chef. The full-size fridge was a difference maker. We used the grill several times for dinners with no issues. Water was plentiful. We bought ice most mornings and always had more than enough, so the ice maker never really got used.
A couple of small things worth knowing. The one AC issue at Leverick Bay was the only real hiccup of the week. Unwinding ran a step slower than the power cats we’ve chartered before, but not an issue. It also seemed a little top-heavy, but not in a bad way. We burned more gas than expected, the bill at the end of the week came in a little higher than planned, though given the speed and the ground we covered, not unreasonable. The tender deck off the back added a lot of extra space too.
This was our second charter through Virgin Charter Yachts. We can’t say enough about them. They take real care of their boats, and when the air conditioning went out they had someone out right away who spent a lot of time getting it right. Nothing else came up all week.
What we’d tell you if you’re planning this
We provisioned through multiple spots. RiteWay for the basics, food, beer, and liquor. Caribbean Cellars for additional wine and spirits. Steakation Butchers for meat, top notch for proteins. They confirmed our order the day before delivery, more communication than most vendors bother with. Boat toys, the water hammock included, came from Island Surf and Sail, booked about a month ahead.
A couple more things worth passing on. Use a broker, even if you’ve done this before, they’re the eyes and ears of the charter industry, they know the boats, ask the right questions, and hold your hand through everything from booking to the day you show up. And if your timeline is tight, a private water taxi from St. Thomas to Tortola is a splurge, but well worth it when you just need to get there.
Don’t rule out a fully crewed charter. You might be surprised by the price difference once everything, meals, provisioning, toys, adds up against what you’d spend bareboat with a captain. Having said that, we wouldn’t change a thing about this trip, but the next one will almost certainly be fully crewed.
The BVI is getting busier too, Soggy Dollar and White Bay specifically. Our last several trips have been busy, but this was by far the busiest, a heavy cruise ship crowd through the early part of the day. It cleared out by early afternoon. We’d recommend heading to the other side of the beach, a lot quieter, Ivan’s and Alice’s own that corner of White Bay. And seriously consider a night or two in St. John after a BVI boat trip, if time and finances allow, it’s a great way to unwind.