Just FYI....

We have had out board motor problems with dinghys.....with the Moorings, Sunsail, and Conch. We would not want to make a dink passage at sea. We also sail the BVI in May, and have been for 35 years. May
brings great sailing trade winds, 11 to 20, our of the NE, or south of NE. Wave and say Bye, Bye, if that dink motor becomes inoperative.

We would also suggest, day anchorage at Deadmans Bay , then motor over to Great Harbor and party down at the Will T with the vessel on a mooring..

We also have professionally lead flotlllas in the south pacific, and caribbean and coastal islands of so calif. . Suggest with two boats, establish your procedures. One boat will be the flotilla leader, and both boats will stay together. Or, each skipper
will chart his own course, and you may plan on meeting up, if winds, and hangovers , or extended time some place really great does not interfere. Have a procedure set , either way.

With no plan, it will be a goat rope, and not good relations between the crews can occur.

The skippers of the both vessels should be highly qualified and experienced as they are responsible not only for the vessel, but for each and every person on board. The OP, is on vacation as well, and up to him
if he wants to add in being group leader . One other thing is that the OP does not want to be worrying about the other vessel.

The flotillas that I lead, Tahiti, Tonga, The Windwards and the BVI as well as 10 to 12 boat training cruises SAILING newport bay to Two Harbors Catalina. ( the training cruise it was requrired to maintain group integrity.and
That was sailing from about 10am until near midnight...no motoring ).

For all flotillas . we had pre cruise meetings, chart meetings, etc, and usually what occured, on he international sailing vacatiions is that the very highly experienced skippers charted their own courses.
The fist timers to bare boat international sailing stayed with me for as long as they wished. But, they had to communicate their intentions.

There you go... just FYI.