would like you to sail in circles within 2 miles of the main base and not break anything.
I agree with btrayfors about USVI and Spanish Virgins. That is the way to go IMHO. First see if the company still allow it. They used to allow one way trips to
PR up to 5 years ago when they closed their base there.
Ask for a boat with a US Decal/US registered as this may help checking in in to USVI (Cruz bay). Make sure all your passengers are US citizens or if not have Visas in their passports (Visa waiver does not apply).
St. John = great, St. Thomas = pit (but good to buy booze), St Croix = so so, but nice long sail. nice day anchorage in Buck island., Culebra = Great, breakfast at Mamacitas, Vieques = Great,
PR = OK.
Remember you are returning upwind. Shout if you plan this route and require more specific info.
Get Pavlidis guide to the area.