Sorry to bump an older thread but I wanted to share my 2 cents.
I strongly recommend taking a cruise out of San Juan, Puerto Rico. Because of its close proximity to all of the top Caribbean islands, you can usually find an itinerary where the ship stops in 4-6 different ports on a 7-day cruise. (Unless you're really into the casino and/or lying by the pool for the entire cruise, more time in port = more fun and less boredom.)
Including taxes/fees, return flights to San Juan from Seattle are typically between $400 and $600 per person. US Airways (a solid airline in my experience) offers daily flights connecting through Charlotte; at the moment the price is hovering around $480 return after taxes/fees.
Another, cheaper option for Caribbean cruises is to leave from Fort Lauderdale. This is still a good option but typically means more days at sea - not the end of the world but will mean a less time in port. Flights to Ft Lauderdale are usually a bit cheaper than San Juan, but it depends on the airline and the time of year. Right now the cheapest SEA-FLL return flights are about $380 after taxes/fees (Delta and United).
There are also Caribbean cruises out of Tampa, New Orleans, New York, New Jersey, etc... but the itineraries typically include more days at sea and you won't save much on flights to any of those places. Leaving from New York is nice if you want to spend a few days in the Big Apple before or after the cruise, but then your costs will really start soaring.
Keep in mind that the Caribbean rainy season usually starts in late May/early June and runs until late October/early November. If you're planning on going during this period, you may be better off with a cruise out of LA as others are suggesting. (Of course, the rainy season also means there are some great deals to be had on Caribbean cruises, so if budget is a big factor then it's worth considering).
In terms of the various cruise lines, there are a few I'd recommend as the most likely to appeal to everyone (not just seniors):
- Royal Caribbean (known for having the best ships, reasonably competitive pricing)
- Carnival (casual, fun-oriented, very affordable)
- Norwegian (innovative programs, usually affordable)
I cannot speak from personal experience but I have heard that Holland America and Princess typically cater to an older crowd. Upscale lines such as Celebrity are more formal and usually more expensive but may have some appeal to younger people.
Your source for all cruise-related information:
www.cruisecritic.com