Has anyone ever rented a small sailboat (laser, sunfish, etc) and hauled it around with them for a charter week? I know you can rent kayaks and SUPs for use on a charter but I haven't seen or heard about a small sailboat. It would be a blast to be able to get a little sailboat in the water and hone my dinghy sailing skills while the rest of my fellow crew is more focused on beach-bars and sunbathing. In the past, I would rent a hobie or laser from BEYC for a few hours but that seems unlikely this time. Is this a crazy idea?

We have never seen or heard of it.

I don't know how well the small sailboat would tow.

You Might be able to rent a hobie at leverick Bay.

Oil Nut Bay Resort has two Hobie cats available and for the time being they are not charging a daily resort fee. I don't know if they allow you to venture beyond the swim buoys.

When we were at ONB plenty of people were taking the Hobies way out past the reef toward Necker. Good fun!

As someone who has spent many weeks on a charter sailboat over the years, and who loves sailing smaller boats such as sunfish, lasers, hobies, I'd say that yes this is a pretty unworkable/challenging situation (hauling/towing another smaller sailcraft) unless you're aboard something in the 60'+ range (multihull). The only thing I'd haul that also sails, would be a windsurfer or kiteboard (which I've done many times/in fact always do) but that's not really what you're considering. However, what I've done on many charter vacations is find smaller boats to sail at different stops, though that's dependent upon where you are and what's available and I suspect is more challenging these days in BVI's post Irma.

Thanks for the feedback - I'll checkout ONB and I forgot that Leverick had hobie cats as well.

There are no small sailing boats that could be safely towed but plenty of large yachts carry lasers and others on deck.