When to go
Certainly, the most crowded time for the Caribbean resorts is Christmas and New Year. But few people know that right before Christmas, many of the hotels have some of the best deals of the year. In particular, if you book your trip in an all-inclusive hotel departing back from your vacation on Christmas day, you will maximize the am0unt of things you can do during your vacation while getting the same deal for a much lower cost than usually.
December 12-23 each year is our most favorite days to travel to warm sunny countries, and the costs of the trips during those dates is usually half of what it costs to go just a few days later.
When not to go
Avoid June – in many Caribbean vacation hotspots, it’s a peak of the rainy season, and the amount of mosquitoes is overwhelming. For example, when we stayed in Akumal, Mexico (near Cancun, Playa del Carmen and Cozumel), in the hotel room along with the standard showercaps, soap bars, body wash, lotion and shampoo, we also found a bottle of mosquito repellent – even with the repellent, the number of flying parasites was overwhelming, and many tourists in our hotel ended up never getting out onto the beach.
Also, avoid August through November – a hurricane season.