Have you ever looked into cruises for such events? They are an amazing way to travel on the cheap if you find a bargain. I am looking at early February (over the 7th) because I like to travel somewhere new for my birthday each year. I have found cruises in the $50-60/day range, and on practically new boats that are so nice, it would blow some people away! Price per day includes unlimited food, activities, and non-alcoholic beverages! Sure you have to add on tips, taxes, and port fees, but well under a $100/day per person is achievable, and it's all inclusive! I'm not sure how it works, but chartering a cruise (in part or whole) will likely make things even cheaper! I'm happy to help out with shopping around if you would seriously consider this as an option.