Is it possible to fly directly from Anegada to San Juan? If so, which carrier provides this service?

No scheduled commercial flights, but there are several charter companies that will do this. I'd start with Island Birds or Cape Air.

I have contacted Island Birds. They informed me that they can't fly directly to San Juan. They are required to stop at Beef Island, presumably to check out of the BVI.

Cape Air told me a few weeks ago that they were not flying to/from Anegada.

No idea why Island Birds would need to stop at Beef Island. We flew from Anegada to St. Thomas in May without stopping. This will be interesting to follow.

Weird. They heavily promote their charter business on their website.

There is this note "CAPE is only accepting Caribbean charter requests for bookings after January 4, 2022. Due to high demand Saturday availability is limited." at https://www.capeair.com/scripts/request_charter.html

Part 121 airlines can and do fly charters all the time. Charters are flown under 135 rules. Delta is one of the largest charter airlines in the world and even has a fleet of 757’s equipped just for charters.

Well, I stand corrected! Thanks, George!

Meanwhile, is there a charter company that flies direct from Anegada to San Juan?

I think we have a member on this forum who flew (charter) Air Margarita from Anegada to San Juan recently . . . maybe she can comment (or correct me)?

You currently can’t fly directly to Anegada as it is not a covid point of entry for customs. What you can do is book a flight SJU-EIS then Anegada. You will clear customs and COVID at EIS and jump back on the aircraft to fly to Anegada. It will be a extra cost.
G

The OP is trying to fly out directly. Can you think of any aircraft clearing rules that would prevent this?

Air Margarita is a good option to try. We've use them in a pinch before when we had issues with Air America Caribbean (who was great pre-Irma).

I miss read the direction. There should be no reason they can’t do that. The BVI might however require the pilot to stop at EIS on the inbound leg.

Not yet, but I think it will be available soon for vaccinated arrivals.

George - based on my experience in April you are correct. We flew STT to EIS. De-planed, got COVID tested and cleared C&I then re-boarded and flew on to NGD. Going the other way we flew NGD to STT non-stop.

Jason - I think so too after seeing how it's being handled at VIJ.

We were there last month and couldn’t make it direct. We flew out of EIS to SJU, went on ferry from Anegada to EIS then flew to SJU on Air Margarita - worth every penny!

Thanks. I wasn't sure how you had to go. Was hoping direct.