Jeannius, we spent time at St. Martin in July. Digicel did not offer eSims then. They are starting to roll them out and now include Anguilla and offer a 10GB plan. You can reload data using the Digicel app. We went to the Digicel store in Marigot to setup an account and get a physical SIM. We had to bring your boat paperwork and St. Martin C&I paperwork to get an account. I am not sure how being on charter would change this.

https://esim.digicelgroup.com/

We used sailclear (you must) for those countries that support it - Anguilla, BVI, Saint Kitts and Nevis, and Sint Maarten. St. Martin and St. Barts each have their own clearance processes. If you do not clear with sailclear ahead of time you will need to use the kiosk at C&I. I understand that you can no longer check in/out of St. Martin at Budget Marine or Island Waterworld. Zanshin any new surprises on the French side? Noonsite.com has details on each country.

We did not have any problems heading down to Grenada, but we spent at least a week at each stop and own our boat.

Cheers, RickG