I'll be sailing a bareboat charter out of Charlotte Amalie in May 2020. I and my wife are US citizens and a couple from England will be on board with us along with a Captain for hire for 8 hours on the first day. We are required to drop the captain off at a port with a ferry so he/she can get back to Charlotte Amalie.

I'd like to make it to Leinster Bay, St. John the first day but the closest port (besides Cruz Bay) is Soper's Hole, BVI.

I'd like to sail into Soper's Hole harbor and have my friend from England take him to shore with the dinghy (I will not be dropping anchor or picking up a mooring). If my friend does not tie up to the dock and drops the captain off, is my friend still required to check in at BVI customs? Or can my friend just drop the captain off and immediately head back to our sailboat without checking in to customs?

I'm asking because we'd like to stay at Leinster Bay the first day and then officially enter the BVI the next day without all the back and forth.

Thanks for any tips!

Follow the rules or deal with the consequences

I'm asking what the rules are specifically with regard to the dinghy going to the dock and my friend not going ashore. That's the point, I'm trying to get clarity of the rules. I already know if you don't drop anchor you don't have to check in (at least, that's the way it is between Canada and the US).

Oh Lordy, no....can't do that. I was in Soper's at the C&I office when someone did just that. The Immigration officer freaked out and made all kinds of threats to the parties involved. Doesn't matter if you take a mooring, anchor or not.

Drop him in Leinster, and call him a cab....it's easily accessible by road. Ferries on the hour from Cruz Bay back to Red Hook.

If you sail into BVI waters for any reason other than innocent passage you must clear customs. Entering a harbor is never innocent passage. This is not even a gray area. The penalties can be very large. If your skipper is onboard for a initial checkout drop him at Cruz bay and then head to your anchorage for the night.

Your check out Captain will know that your BVI plan is not a good one. Dropping off in another country without checking in is naive, illegal and not a good plan anywhere.
I have sailed US/Canada waters often and know they would not allow dropping of someone in another country that way.

You do not have to get him ashore at a 'port' -- I have been that check out Captain a few times myself, and would suggest Maho Bay STJ as a much easier drop off point for your itinerary. Closer to the road and Much! easier to get a ride to Cruz Bay. About an hour motor up to Leinster Bay afterwards if that is what you want to do, NPS moorings in both places.
Take every advantage of the knowledge that your captain can impart -- on the vessel systems, the boat handling, the rigging for raising, reefing and dropping sail, safety concerns, navigation suggestions, mooring pick up practices, dinghy operation and handling -- but particularly the vessel systems for power management, system operation and maintenance and troubleshooting.
It is a huge bonus to have a knowledgeable sailor familiar with the vessel, waters and in this case Rules, on board to start a charter - it will give everyone on board a chance to ask questions that would only distract you as Captain of a new boat in new waters the 1st day.
Any charter company that sends a vessel out breathes a great sigh of relief if a Check Out captain is aboard for the 1st day -- it greatly increases the probability of a successful and trouble free charter for ALL involved and will make your job as captain for the duration considerably more effective and [hopefully] stress free.
FWIW
This all is only my opinion - except for the BVI drop off - from my experience of decades on every level of chartering from being a guest, crew, employee and Captain
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Very helpful comment.

No, I should have gone into detail.

LocalSailor thanks much for sharing your wisdom and experiences!

Thanks! I'll look into this

Thanks for the tips everyone. Very much appreciated. I fully intend to follow the rules, just needed some clarification.

Thank you!

If you want to go to Leinster Bay, St. John, why are you going to the BVI first? Why doesn't your captain take the ferry back to St. Thomas from Cruz Bay on St. John, right next to Leinster Bay. The next day you can go over to the BVI and be fully legal.