Christopher,

May I suggest Roberts on Cowpet Bay.
It meets most of your criteria, but the most important "Caribbean Cuisine"
However the food is wonderful and many of the dishes integrate the Caribbean Flair
They do have live music, but I am not sure it is regularly scheduled.

I am getting old, but there is a lady who plays often with Jazz folks over in STJ at the beach bar that plays at Roberts and I forget her name...
She is great - I apologize for forgetting her name.

For a not so refined dinner - I like Latitude 19 on open mic night
That is a roll of the dice. Some great local bands, members of different local bands jamming, folks from the mainland, and even Kenny Chesney has taken the mic. Food is ok - seafood is fresh bar food - it is on the water - life is good. I think that is Tuesday. Maybe eastender or someone can confirm.

Not sure if I recommended your perfect place, but rest assured you will not go wrong.

Hey, TomB, don't go switching our latitude! It's Latitude 18 m'son and you're right, the open mic night is on Tuesdays!

I'm a fan of Blue Moon Cafe at Secret Harbour. Romantic, right on the water, excellent food with many items "Caribbean flair" and at a reasonable price. Have fun! Cheers!

Come on what is 69 miles among friends
sorry for the typo

Some suggestions closer to where you are (town):

1. Walker's By the Sea. This restaurant serves Caribbean food and is on the water at Emerald Beach (near the airport). When Walker's cooking, the food is supposed to be very good, but you never know when he's cooking. This is one place where people of color who are born in the Caribbean like to go for dinner.

2. Victor's New Hideout. Another favorite with locals, and has a fantastic view, but it's on a hill not near the water.

3. Oceana in Frenchtown. Beautiful restaurant on the water. Menu may be more European, though.

This one isn't in town, but it's got live music:

4. The Lobster Grille at Bolongo Bay Resort has water view, and is supposed to have live steel pan music on Saturday nites. Known for their Caribbean lobster dishes.

TomB - 69 miles in any language is, well, 69..... ho ho ho. Time for the Old Tart to go bye-bye. Cheers!

I had dinner earlier this week at Victor's Hideout - extremely good native food, excellent service and a beautiful early dinner/sunset view -- They do not have live music - and I would say it isn't really a romantic ambiance, design wise but there were quite a few couples dining - your conversation is private - and the staff was very friendly,attentive and helpful. You could certainly feel comfortable during dinner and if food is the criteria I will recommend it highly.
We had Conch in butter sauce, Old Wife steamed with onion, conch fritters, fresh salad, fungi, rice and peas, plantain, sweet potato, and some top notch homemade hot sauce.

Cuzzin's has wonderful local food and drink- from lobster, tender conch and local fish (try the old wife) to curried mutton and stewed chicken with all the sides. A great place to try green banana, plantain, fungi. Also local drinks such as soursop, tamarin, seamoss, passionfruit or alcoholic ones such as bushwhackers, iguana colada, etc. It is in a beautiful historic building, although it is not overlooking the sea. (tu)

Second that Cuzzin's!

I third Cuzzins! It's downtown and doesn't have a view, but the building is very cozy, romantic, old brick and wood, and has fantastic food including a sampler plate. It's what I recommend for real local cuisine.