Hi, Kent & Carol.
I've done the Caribbean 1500 three times, and can highly recommend it. This year there are 75 or so
boats in the fleet, which gives you a chance to meet a lot of folks, many of whom have been to the islands before and can offer a ton of information. There's a lot of comraderie and a party atmosphere, but they also provide a lot of good information for first-timers to the Caribbean. You'll run into folks that you've met time after time as you
cruise the chain. The included
weather briefings and enroute updates have been very accurate and helpful in recent years (there have been some accuracy issues in the past).
The advantage of the
offshore route is that you get to the Lesser Antilles quickly--a week and a half or so. Harriett pointed out the disadvantage--you miss the
ICW, the
Bahamas, T&Cs and the DR on the way down. Of course, you miss that upwind beat from
Florida, too.
We
cruise with a cat who never goes ashore, so we had no difficulties when clearing in to any of the islands. You are always required to declare any
pets aboard. Some islands (the ones that have managed to avoid rabies) forbid the landing of
pets, on other islands it's allowed. The rabies-free islands take it very seriously. A cruiser we met in Bequia told us that he took his dog ashore there for a potty stop, and was challenged by a
customs officer who said if he ever brought the dog ashore again, it would be shot on the spot.
We sail with a cruising spinnaker, and I was able to use it for a day on two of the southbound passages. I've used it a few times in the islands,
Guadeloupe to
Antigua, for example. I agree with Harriett--don't buy one just for the islands, but if you already have one, take it with you.