San Juan is fine. We usually overnight there (six trips in past year). Twice now we have stayed at the AC Condado Hotel, which I would highly recommend. It’s one hotel back from the beach, but you can use the Marriott beach across the street. AC has a terrific rooftop bar and breakfast area. About two blocks down the street is Cayo Caribe, a great Puerto Rican restaurant.

We used to stay at the airport hotel for convenience, but post-Irma it got very expensive for nothing.

We use Cape Air if it’s part of a United ticket, but otherwise we are happy with Seaborne. InterCaribbean’s luggage allowance is too strict for us.