We have a 1-hour connection in Miami before landing on St. Thomas Friday. We then have a 3-hour gap to catch the ferry, then make way to Tortola. Our charter starts that next day, and we are off!

We have plenty of time to catch the ferry so I am not worried about that. Both of our flights are on American so if we miss the connection in Miami, I'm sure we can figure it out and be there in time for our charter the next day. My biggest concern is if our luggage misses the connection. Would American be responsible for tracking me down in BVI or would I have to go back?

Of course, this makes me want to just carry on and I know the drill about less clothes than you think you need. Hell, I could probably fit everything in a backpack, but I am the captain, and our crew likes lots of gear and toys (drone, flags, Christmas lights, lots of etc). I am most curious about how much hassle it could be tracking my bag down on St. Thomas if I have crossed over into BVI and possibly even started our charter.

I've wondered this as well and frankly, I think you and I both know the answer - it would be a major hassle. I'm telling my guests that if their luggage doesn't make, they won't see it until we get back. Basically, they HAVE TO make it fit in a carry-on.

I'm not sailing back to Tortola (or wherever) to pick up luggage that has finally made it somewhere in the middle of the trip.

Maybe I'm wrong an American will ferry it out to me on me ball at Anegada but I don't think so...

I use Stanley from Love Cab as my driver on STT. If a bag doesn’t make it he handles it and gets it on the ferry to Tortola. I suspect other drivers people use do the same. Worth a few bucks more than the cab line at the airport.
Stanley
Ph:704 473 6344

This happened to one of our guests last year. They arrived late afternoon and her bag missed the connection in Atlanta. Her bag arrived in STT the next day and Delta got it to the ferry. But it was on us to pick up the bag when the ferry arrived at 3PM.

Fortunately, we were in a slip at Scrub when they arrived so we just extended an extra day. We lost a day of sailing but at least were able to enjoy the beach and pool at Scrub.

We pack everything essential in a carry on - clothes & toiletries. We check our cooler and another bag that has the "nice to have" stuff like snorkel gear, yeti cups, beach towels, etc. If our checked bags don't make it, it's an inconvenience, but doesn't ruin the vacation. We can always get snorkel gear at the charter base and pick up the other things at the store if we really need them.