I have signed up for two BVI charters with total strangers. In 2014 I did my Intermediate Cruising course (aligned with Canadian Yachting Association) with 5 other people (including one instructor).

In 2016 I signed up with a flotilla organized by a sailing school from New Jersey where I was on a 50 ft Beneteau with 7 other people, none of whom I knew before the trip but who all knew and sailed with each other (making me the odd one out). That was two years ago and all of us are joining up again in February 2018 for our third charter together.

It can be a bit of a leap of faith to sign on to such an outing but I was travelling solo which allowed me to be a bit of a chameleon and mold myself to the people I was travelling with. In both instances everyone got along (we are all afterall, adults) though the first trip saw a distinction between those who wanted to party a little harder than the others.

People who know me well say that signing up for these types of trips is way outside my comfort zone (and they be right!! lol).

I don't want to sound like I'm doing a commercial here but the organizer of the February trip takes on couples as well as solo travellers. There are also a variety of boat sizes to choose from 45 ft, 50 ft monohulls plus a couple Cats. He puts couples travelling together on boats with other couples. But as part of a flotilla (typically 7 – 9 boats!), there are enough people at the various stops that you can socialize with people not on your boat if the chemistry isn't working. However for a week, my experience is people find a way to get along with one another since they have a common interests in sailing, travel and the Caribbean. If you want, send me a private message and I can give you the contact info or I can publish it here if the Moderators don't mind.

D