Different strokes for different folks - I've only gone to Jamaica and stayed less than 2 weeks twice. My minimum amount of time because I'm travelling from California was always 3 weeks. As time went on and my life allowed I started staying first for a month, then 6 weeks and now we stay for 3 months. Since my work is somewhat seasonal the time span when I go is exactly when I CAN go and rather than travel 3 or 4 times for short periods during that three month span I prefer to just stay. I have a great situation with a house rental, I'm a part of a community there...so now its really just about going "home" for the winter.

For me multiple trips are not only spendy but the travel time would kill me - 12 hours door to door 3 or 4 times in 3 or 4 months? Thanks, no. I spend enough time on airplanes and in airports throughout the year!