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1 month stranded in the Caribbean, the French Polynesia etc. is the least relaxing thing I can ever imagine.
Cuba is a great place to be if you like diving/snorkeling. How about going to Europe? It's within your budget and not too much of a flight away.
I'd probably pick Mykonos (beach, pool, sea, plenty of attractive women who are there for their summer retreats, all the right conditions for a high win rate) in your position. I'd see if it's within your budget to rent a boat and move around the islands. Another possible way is to start out in Turkey (e.g. Bodrum) where it might be better to rent a boat. Elounda and Santorini are amazing, too.
I'd also recommend a circuit around Spain, e.g. San Sebastián, the Canary Islands (e.g. Tenerife, Gran Canaria) - lots of things to do on the islands, and plenty of women too.
Alternatively, Albufeira and Algarve in Portugal. I love the food in the Portugal, the place is cheap , and the women make good company.
Or Costa Smeralda, Sardinia, great balance of beautiful clear waters, white beaches and good resorts.
1 month is a long time, and you'll rack up a lot of points if you're staying with a hotel chain's loyalty program - if you haven't signed up for one already - and spending your vacation entirely on a matching credit card (e.g. Starwood AMEX, Hyatt Chase). The reward card programs all come with a first 3-month expenditure bonus, so you'll easily hit it if you're going on a vacation. Starwood has a great selection of resorts in Europe. Hyatt has pretty good ones in the Caribbean and one in South Africa. If you're in a typical place like Waikiki or Puerto Rico which has a lot of resorts lined up next to one another (e.g. Hilton, Sheraton, W) you could probably hop between 2 resorts on alternating days so you will rack up points really quick and not feel bad about not tipping the cleaners. If your planning is good, you can rack up enough points to recover $1,000~2000 in expenditure. (I do this every Christmas/New Year season, when you can arbitrage the points and rewards system.) If you do pick this route, let me know as I have some recommendations.
I see. True, a cruise around the Caribbean would be nice, so long as you're not stranded on an island whose industry revolves around registering 5,000 companies in the space of 700 square feet, and charging $10 for a bottle of water.
I personally hate the Miami/SoBe area, although I've never been to Ft Lauderdale.
Been looking at cruises. Leaning towards that now over a resort. Galveston is only a 4 hours away, I've driven it many times and there are a few choices for cruises out of that port as well.
I've been on Princess and Royal Caribbean so considering Carnival this time. Found this pretty fun passenger video of the Carnival Magic:
Big ship - 3700 passengers + 1500 crew, but from the other videos and pics I've seen it's manageable and not over crowded.
If you mean Bruno Mars (?), that's the first time I've ever heard a song from him to my knowledge. It's a catchy song, the guy who made the youtube cruise video did a good job with it.
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