terradactylexpress said:
Look at me. I'm so rich and/or stupid that I plan hurricane season beach vacations every year
Far from rich. I think I already explained it before, but the late summer and fall is one of the best times of the year for diving the Caribbean if you like calm seas, warm water, and light winds. Unless there is a hurricane around, it is great diving. It is also low season in the Caribbean for the resorts. So they offer big discounts and many of them even shut down for a month or two depending on where they are. You can get great conditions for diving, cheaper prices, and less crowded destinations. You just have to be willing to keep an eye on the tropics and be flexible enough to change your trip if there is a storm coming.
In the case of Ivan in 2004, we just changed our dates to go about a month later and the resort and airlines charged no change fees. In the case of Wilma in 2005, it was barely a Cat 1 when we made the decision to go to the airport and go ahead with the trip. According to the NHC, the "models were in unusually good agreement for this far out" about the track over western Cuba, putting Cozumel well away on the dry/weak side of a weak storm. While we were getting up very early and heading for the airport and flying down to Coz, Wilma underwent explosive intensification from a Cat 1 to 5 in about 12 hours. When we arrived and checked in, then checked the NHC again, the models had all changed and it was coming right at us. The Continental flight we went down on was the last flight of theirs off the island and we were stuck.
Since getting stuck in that storm, we both won't even consider flying into a location near the forecast path of a storm, no matter what the models say about where it is going. But we have taken over a dozen trips to the Caribbean since then, only one not during hurricane season. We have had to change plans to move the trip by a week or two 3 times since then due to approaching storms, but have never had to pay a change fee and never needed trip insurance.
Just as an FYI for those buying trip insurance, one of the reasons we did go down for the trip ahead of Wilma was that we had bought trip insurance for that trip. When we called them to see what their coverage would be if we changed the trip, they said if the airlines were flying and the hotel was open when we were supposed to go, they would cover nothing. Since it was forecast to be a weak storm over Cuba and nothing was shutting down on Coz. Since that time, we have figured out that most of the resorts and hotels don't want to have to deal with guests being present with a storm coming, so they are more than happy to rearrange your dates ahead of a storm that is approaching. Most of the airlines now also do no change fees/fare if there is a named storm approaching a location. So if you are dealing with reasonable/reputable resorts and airlines, trip insurance may have very little to offer you for what you spend.