Looking at a 7 day bareboat to Martin / Anguilla / Barts.

Can anyone describe the customs and immigration process? Do we need to clear out of Martin, get a zarpe, then into Anguilla? Repeat from Anguilla back to Martin, Martin to Barts, etc? Can the captain (me) do it for everyone or do all crew need to be present?

Probably tight to see all three islands in a week, weather permitting.

Thanks for any guidance you might have!

C&I when clearing in and out can take from 10 minutes to over an hour; but is a relatively simple process.

1. First you need to clear out. The captain (and only the captain) goes to the office with the boat's paperwork (registration) and the passports of everyone aboard and fills out the form(s). Once you have pratique (the outbound clearance), you have 24 hours to leave the country.
2. When entering foreign waters, you fly the yellow flag on the starboard spreader and the captain (and only the captain) takes the paperwork, passports and exit clearance to C&I and fills in form(s).

This process repeats for each country. Which side of the island are you chartering from - the Dutch or the French? If on the French side in Marigot you can clear out at the Island Waterworld store or the ferry dock, or you can clear out at my favourite location in Anse Marcel. Clearing in on the French islands such as St. Martin and also St. Barths is identical, they have a standardized identical French system and the costs are usually around €5. The non-French islands are different and not as relaxed or cheap.
Anguilla uses the https://www.sailclear.com/ online system. Clearing into and out of the Dutch side is done at the Simpson Bay Bridge police station.

I've been clearing in-out for years and on most of the islands. I always wear a clean polo shirt and shower/shave beforehand and bring my Kindle for reading material. It can take 10 minutes if all goes well, but I've often had over an hour of waiting - hence the Kindle.

There is one extra thing to be aware of on the French islands, on a charter boat. The forms are quite long and the keyboards are French (some characters are in different places compared to a U.S. keyboard so don't try and touch type!!!). Charter boats that have been to the island before will already be entered into the system but, you need the password for the boat. The guys behind the desk in the Capitainerie USUALLY know the password and if you get that, it'll save you a load of typing.

Don't be put off by the procedures, it is well worth the effort to get to these other islands. I did a trip with Dreamyacht last month out of Anse Marcel, St Martin (Zanshin is right, that is the best port to do the formalities on St Martin). We didn't get to Anguilla this time but went down to St Barts, Nevis and Montserrat and the formalities were easy and actually pleasurable on all occasions.

As @Jeannius stated, the system in St. Barths is different from the standard French one and does indeed allow storing the boat name to save on typing. The folks at the Capitainerie also have access to the passwords for the charter boats, so if you don't have it with you, they'll give it to you. The closest computer to the desk also sports a U.S. keyboard (QWERTY rather than AZERTY) to make life easier for the non-French.

Thanks for your help! We will be chartering from Navigare's new base in Marigot with plans to arrive in Anguilla in Road Bay (is there a place to clear in here?), spend a few days, then circle back to Martin for one night (Anse Marcel or Isle Tintamarre), then on to Barts for a few nights (Colombier, Gustavia, etc), then back to Martin. Are you saying that we can do the Anguilla process entirely online via sailclear or do we still need to visit the C&I office? Thanks again!!!

Anguilla... Only the paperwork is completed online. You still need to attend C&I in Road Bay. They were very relaxed and friendly last time I went, admittedly a few years back and it was a quick process. If you want to visit any other Anguilla locations by boat, you'll need to purchase a cruising permit. See Noonsite LINK

Ans Marcel can get a bit rolly (unless you have a catamaran, in which case you are good to go there), and Tintamarre is frequently too rough for a good overnight stay, but Tintamarre is just a bit further and I've always gotten a mooring ball there. And should they all be taken, Anse Colombier on St. Barths is just a little further and there's always room there - if the recommended mooring balls (free) are taken, you can anchor there.

Wow. Conflicting info....

Noonsite says $110/day for a cruising permit. Navily thread below says $210/day! .... just to cruise over to Little Bay or Crocus or Rendezvous in a 45' cat where you can't really spend the night anyway? Apparently they've shut down anchoring in Crocus:

https://www.cruisersforum.com/forums/f19/st-barts-st-martin-anguilla-7-day-itinerary-274743.html

$87 for a mooring in Road Bay?

https://www.navily.com/mouillage/crocus-bay/13011

https://www.noonsite.com/place/anguilla/view/fees/

https://www.navily.com/mouillage/road-bay/13010