Get hot holiday savings, travel inspo, and expert tips & tricks straight to your inbox. Panama may not be what comes to mind when thinking of the Caribbean, but if you’re chasing the experience rather than a technicality, you’ll be thrilled with this alternative. Sitting south of the hurricane belt, it offers gorgeous beachfront locations with relatively low risk. The first spot on your list should be the Bocas del Toro archipelago, a group of paradisiacal go through here islands that are particularly sunny in September and October even while the Caribbean gets pummeled by rain. Known all over the world for its bouncing reggae tunes and high-flying bobsled team, Jamaica is among the easiest and cheapest Caribbean spots to reach from the mainland US. There are countless low-cost fliers running routes from hubs like Miami and New York to Montego Bay airport. From there, it’s a quick transfer to condos and villas in Negril and Ocho Rios, which have got some of the very best beaches on the island.