Cuba
I went to Cuba (Varadero) in February in 2003 and had an excellent trip. Cuba has lots to offer. Lots of historical sights in Havana. Depends on what you are looking for. Weather was great, 25 degrees on average, did a lot of stuff off the resort such as a 2 - day trip to Havana (including the Tropicana show) , a day trip on a Katamaran to Cayo Coco, took a 25 minutes scooter ride to a small town called Cardenas, flea markets in downtown Varadero, etc.... In terms of hobbying for chicas, I had great success in both Cardenas and Havana. Hobbying in Varadero, is more of a challenge, not impossible, but more of a challenge.
In terms of bookings, depends on your budget. I've always booked about a month ahead of time and got a good deal. Last minute bookings are often cheaper however you might have less choices of locations.
Dominican Republic (Puerto Plata or Sosua Bay) is also a good 2nd choice.
