My wife and I have been on the Adventure of the Seas three times on (basically) the same itinerary (Southern Caribbean) out of San Juan. We went on her for our 15th and 20th wedding anniversaries with one extra trip in between.
Although we do not mind the smaller ships, without the Royal Promenade, it just seems like something is missing. Our children have not been on a bigger ship yet and they are really looking forward to the Freedom of the Seas in November.
Living on the Gulf coast, we too are within driving distance of many departure ports. My problem is that being active duty military, I only get 30 days of vacation per year. Now, I know that may sound like a lot, but please keep in mind that when going away from home, I must also take vacation on non-work days. On my last cruise in January, I had to burn 10 vacation days for four days off of work! It was over a holiday weekend, so there you go. I basically only have the vacation to take three cruises per year max (assuming at least seven day itineraries) so I guess I will have to wait until I get out our retire to cruise more frequently. Not to mention the fact that my wife actually wants to go visit her family as well. What a waste of time that is (just kidding, of course).