Odinson,
Seacliff hotel looks real nice
https://www.airbnb.com/rooms/15026365
I too would love to stay there.
I second Woody's Ms. Cherry has the best rum punch on the island!
Trident has jazz on I believe Saturday nights
Food at Geejam is very good and as stated ask for a tour of the property
Enjoyed the food at Bikini Beach as well
Jerk sausage, Pork and festival at Boston, Haven't gotten a good batch of chicken
Long Bay is really lovely can't swim because of the strong under current but nice to just enjoy the vibe and grab a bite to eat etc
Winnifred is a nice local beach with zero harassment
Frenchman Cove you do have to pay but it's worth it.
Portland is truly special!