Umbrella -- always bring a travel-sized umbrella no matter where you go. In springtime in places like New York City a sudden shower will leave you drenched as you try to hail a cab. If you don't bring it with you then you are forced to buy it, and in a big metropolitan city that means paying $15 for something you can buy for $6 at home. Make sure it's small and compact and fits easily in your purse.
Poncho -- if you're going to be outdoors in a tropical location where it rains a lot or in a place that is generally known for rain, bring a poncho and an umbrella. If it's windy, an umbrella will not keep your clothes dry. A poncho enables you to freely walk around without concerns about getting soaked. For example, in Disneyland a poncho will keep you dry if it suddenly rains in winter and the same goes for Walt Disney World where it is famously wet and tropical.
Windbreaker -- if you're traveling some tropical and warm, you won't want a full coat. You will get too hot and still get wet. Bring a thin windbreaker you can easily stuff in your bag and pull out on a wet, tropical day. Make sure it has a hood to cover your head so you don't get wet. REI sells some fantastic windbreakers in all different sizes and colors. A durable windbreaker never goes out of style and lasts a lifetime.
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