Are you traveling with kids/teenagers? or just you and your other?
DW and I looked into doing one as well except in the off season or winter the ships moved to southern ports so we had to add airfare which just turned us off. We wanted to leave out of NY, NJ, DE, or MD. (4 hour drive or less). Then we had a kid and all our discussions turned to Diapers and Binkys.
Matt O 2006 Skyline Nomad 27' travel trailer. Previously owned 1986 Coleman Columbia / 1992 Coleman Senecca / 1989 Born Free Class C RV.
Before camping my DW, DS and I were cruisers. We went exclusively on Royal Caribbean because we never treated us wrong.
Off season cruising can be difficult due to it also being hurricane season, I'd suggest cruise insurance in case you have to cancel.
Since your forum people I'd suggest you going to Cruisecritic.com, they have one of the largest forums on the internet. You can find a wealth of info there.
Personally my first suggestion is to splurge for a balcony, interior rooms though cheaper can be a bit claustrophobic! If you decide to go and you'll be stopping at Jamaica or Grand Cayman PM me, I have connections! ;D Any questions, just ask.
Cruises are fun. To me, they're like vacation samplers - short stays in each port, just to get a taste.
Unless you're just going to do some shopping, I'd recommend checking out the ship sponsored excursions, and sign up for them early in the cruise. While you *may* be able to get the same thing done cheaper by scheduling it yourself, the ones that are ship sponsored usually will make sure you get back on the ship in the event of an issue, or they'll fly you to the next port.
We've used Carnival (1 time - Honeymoon, 10 years ago) and Royal Caribbean (2-times both after DS#1 was born, but before DS#2), and all were positive experiences. It's still very warm in the Caribbean during the late fall. The last cruise we went on was in early November, and I recall doing at least one snorkeling excursion.
Usually they have backup plans in the event of a hurricane getting in the way. On the last cruise, we were supposed to stop in Cozumel, but it was horribly battered by a hurricane two weeks prior. We wound up stopping in Costa Maya instead.
The Carnival Pride out of Baltimore is nice, in a Las Vegas casino sort of way. It's small for a modern cruise ship (900 feet or so) but nothing larger can fit under the Key Bridge. Goes to Florida and The Bahamas. We've gone twice. Once by ourselves and once with the kids and had a lot of fun and relaxation both times. The shore excursions and shopping can get expensive quick and the drinks on board are exorbitant and can add up quick since they get charged to your room, but other than that you have zero worries and the staff will bend over backwards to make you happy. One other thing, parking is $120 a week at the port. We have friends drive us, but you might consider looking at some of the garages in the city or even the airport and see if you can get a better rate even with cabfare.
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