Look at St. Martin - has everything you want.

"nice beaches that has a tropical feeling" Well, that narrows it down to 90% of the entire Caribbean!! LOL

Unfortunately, "good outdoors entertainment at night" usually means the islands that are busier, sometimes meaning bigger resorts. The more quiet & laid back the island, the less nightlife you will find. There needs to be a happy medium somewhere.

Nightlife means different things to different people. Some people are okay with a laid back beach bar, without any band or any type of show. Some people want the band, the show, etc.

Again, if you want laid back and quiet without the mega-resorts....you may have to consider that the nightlife will be quiet as well...

You tagged Curacao and I think that would be a good fit for what you described. We stayed at the Lion's Dive. There are 3 restaurants on site and several more within walking distance. Hemingways bar was the place to gather at night for drinks and conversation. Down the way at Moomba's was more lively if your are looking for that.

We went in a May and it was not crowded at all. Only handful of kids. They offer 2 bedroom condo type apartments, which would work for you and your friend. They were constructed in 2009, so still fairly new.

There are several places in town that we wanted to try, but we found the public transportation to be lacking. You really need to rent a car there.

Here's a site regarding nightlife and entertainment:

http://curacao-guide.info/activities/nightlife/

Why did you leave out barbados?

Thanks guys, will check out St Martin and Curacao a bit further.

"nice beaches that has a tropical feeling" Well, that narrows it down to 90% of the entire Caribbean!! LOL

What I was getting at is that I went to Barbados for example and wasnt impressed at all. The vegetation didnt have a tropical feel and I read somewhere that due to the differences in weather the vegetation can vary quite heavily from island to island...

look at negril

St.Martin (not St.Maarten), Orient Beach area

What about St.Kitts? the beach at Frigate bay has a quite a few beach bars, Ziggy's stays open til the last person leaves There are some other lovely beaches (south friar beach with Shipwreck Bar is my fav) with nice laid back beach bars as well.

Timothy Beach Resort is the best place to stay imo, it's on Frigate Bay beach.

http://www.discover-stkitts-nevis-beaches.com/south-frigate-bay-beach-st-kitts.html

Hotels in St.Kitts are not expensive either, island is not too crowded, and it is lush and hilly. There's the Marriott to walk to as well (from TBR) where you can get a day pass (awesome pool).

Thats great, thanks everyone.

I've narrowed it down to Curacao, St Martin and St Kitts...all seem to check our boxes

Any more thoughts on which of these 3 you'd go for would be much appreciated!

Curacao is on a smaller scale and it sounds like it would fit your wants very well. You can also enjoy some good local meals. They include things like 'stoba' dishes (meat or vegetable stews), side dishes like funchi (polenta-like dish made of corn meal), tutu (side dish made of cornmeal containing mashed beans), fried plantains, fresh fish and more. Of course, you will find all kinds of food there.

Of course, we also loved the beaches and the nightlife there.

St. Maarten/St. Martin is my recommendation. Dutch and French on one island. Has lovely beaches, plenty of restaurants and has quiet and lively spots. Curacao is quaint but won't be as lively as St. M. Never been to St. Kitts so can't comment on that.

Have you looked at St. Lucia? Has that tropical feel. Also maybe Dominica? That's much smaller so may not have the lively nightlife you want. Def. not Aruba if you're looking for tropical. We enjoyed Aruba but it's more of a Caribbean Arizona!

I have to agree St. Martin has pretty much everything you mentioned, including 37 beaches. We have gone the last two years there and loved it, but this year we are changing it up and going to Curaçao for the first time. Hope we like it! Let us know what you decide.