Chesapeake Family's Bareboat Sailing Charter in the BVI

When the family takes a weeklong holiday sailing charter...

SpinSheet Century Club member Brian Disque enjoyed a bareboat charter vacation through BVI Yacht Charters with his wife, Andrea, and two teenaged daughters, Cara and Lily, out of Road Town, Tortola, British Virgin Islands (BVI). Here’s what he had to say about this special Christmas-week charter: 

view from deck of a charter boat in BVI
Entering Virgin Gorda... what a view!

How did you choose this particular charter boat and location?

We had chartered previously in the Abacos, Bahamas, and Newport, RI. By reputation, the BVI seemed like a great “next” place. We found the charter company via a Google search and visited their booth at the Annapolis Sailboat Show. The Jeanneau 440 seemed like a good boat to charter. It proved to be an easy boat to sail and was very comfortable.

man on deck of charter sailboat
Brian wishing the trip didn't have to end.

Could you summarize where you went and/or favorite anchorages?

We got a nice chart brief from the charter company on day one and planned to sail in a counterclockwise manner around Tortola to maximize reaching in the prevailing trade winds. We found a different anchorage each night except for Virgin Gorda, where we stayed for two nights since it was Christmas Eve. We hit all the highlights in the BVI, with my favorites being the islands of Virgin Gorda and Jost Van Dyke and anchoring in Sopers Hole (Tortola). 

woman sailing a charter boat
The sailing was unbelievable, with the trade winds providing consistant breeze. 

What were the sailing conditions like?

The sailing was unbelievable. The trade winds provided a consistent 15-20 knots of south-southeasterly winds which made for excellent reaching in the Drake Channel. 

We only had one day of stronger winds. We were leaving Virgin Gorda for Jost Van Dyke. We were very sheltered inside Leverick Bay, but we knew it was going to be windy. I unfurled a double reef’s worth of sail, and we blasted across the Drake Channel at seven knots with about 30 knots on the beam. We even put lifejackets on at some point. Overall, I loved sailing there, the deep blue water, blue skies, and mountains… sigh. 

Tell us about your excursions… diving, exploring, other?

We had a lot of fun on land. We did a dive while we were moored up in Virgin Gorda, which was better than I expected considering the winds. Visibility was good. We dove on a pinnacle which is always fun. We also went to the Baths. As much as we enjoyed the Baths, I think the taxi ride over the mountain was just as memorable! We ate at many great spots and enjoyed a cold drink or two.  

Three highlights on sea or land:

A couple of highlights for me: coming into Virgin Gorda, feeling like we were just consumed in this massive valley was really cool. Our passage to Jost Van Dyke stands out because as a Bay sailor, I just don’t sail in ocean conditions as much as I would like to. For us to successfully get the boat and ourselves to a safe harbor in sporty conditions followed by a frosty drink at Foxy’s was really cool as well as getting a drink at Pussers, which had just reopened after a hurricane (2019). Being an Annapolis sailor, I was pretty familiar with Painkillers. Somehow, it tasted a little bit better in Sopers Hole!

Did anything surprise you about the trip?

Overall, I feel that the amount of information available on sailing the BVI and the chart briefing provided good expectation management; in other words, everything happened pretty much as we expected.

Would you do anything differently if you could do it over? 

I would have liked to have hit Anegada or perhaps the US Virgin Islands but was overall pretty happy with the itinerary. If I could go back and do it again, I’d be content with that. If anyone is going and needs crew, I’m game.

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