While staying in the British Virgin Islands, I knew I wanted to treat the family to a full day sailing around the islands. We had a similar outing in Malta, and it was easily one of the best days of that trip. Rosewood Little Dix Bay recommends two different outfits for a day sail, one being a catamaran (which you see all over the place down here), and one is a truly legit sailboat. I had originally attempted to book through the catamaran company, however they required 100% CASH deposit via wire transfer including 15% gratuity paid up front, and sent me a contract that was inconsistent on it’s face. These were totally unacceptable terms, leaving me with no recourse should something happen, so instead we booked our day sail through Bowline Yachts, a small, friendly, family owned business. Booking was smooth, requiring a deposit, and credit cards were accepted. The balance of the trip was to be paid on the day of the sail and could also be paid via credit card. Sarah, the wife of the owner of the Yacht was lovely to deal with via email, and was very responsive.

It ended up being the perfect day to sail (most days are!), and we had a blast on this classic sailboat. This particular yacht, a Hinckley 56, named Pelagial, is super cool looking, and very comfortable. Our captain was Zoltan, a charismatic and funny expat from Europe, who was really fun to hang out with. First mate was Nick, the owner’s son, who was super chatty and really helpful throughout the day. Both Nick and Zoltan are low-key obsessed sailors, thumbing their noses at the gobs of motor-powered catamarans and speed boats that passed by, which made our experience feel even more authentic. I would note that their brochure indicates that they can accommodate 10 people, but I don’t really see how this would be possible. I think the vessel is more than comfortable for probably about 6 people max, although Nick seems to have some grand plans for more seating around the yacht for the future!

Included in the price of the sail are all drinks and snacks, although there was a bit of a snafu with our reservation, so there wasn’t fresh fruit or other snacks they would typically have. It was totally fine, though, since we headed over to Cooper Island for a bit of a change of scenery and a pretty large lunch.

Cooper Island is a small resort that has a really nice restaurant, rum tasting room, nice bathroom and changing facilities, beach club, and gift shop. There are only eight rooms here and the place is not crowded at all, even though there were quite a few boats moored along the shoreline.

We started our time here with some really epic snorkeling, which was some of the best we had in the BVI. Close to shore, we spotted cool fish and corals, but also sea turtles and starfish!

We ate lunch in the Beach Club, which also has a solar-powered microbrewery, so we sampled some of the delicious beers too. It was a bit pricey, but that’s understandable considering how remote this place is. We started off with some delicious conch fritters. I had a totally enormous lobster roll, which was one of the best I’ve had anywhere. Cooper Island had such delicious food, beer, and such great snorkeling, that I would definitely consider staying at this truly boutique resort if we return to the BVI!

After a few hours hanging out and about on Cooper Island, we boarded the dinghy back to the yacht, and set sail towards the Dog Islands, where we were able to snorkel near “The Chimney” at Great Dog Island, a famous scuba diving site.

Eventually, we made our way back to the Virgin Gorda Harbor, tired, but very happy after our day of slowly meandering around the British Virgin Islands on this very cool vessel. The teens absolutely loved our day bumming around the islands, and if you’re considering a day sail out of Virgin Gorda, I would highly recommend booking through Bowline Yachts.