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September vacation with toddler: Mexico? Puerto Rico? St. John?

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Hello! I'd love some help deciding where to go on a family vacation with our toddler (he'll be almost 3). I know September's not the most ideal time to visit the Caribbean, but that's when we can go so we'll make the best of it!

Our other limitation is that we're traveling with American Airlines frequent flier miles. So, we're looking at non-stop options from NYC, but it must be on AA. Looks like our options could be Mexico, Puerto Rico, Virgin Islands or maybe Antigua.

We'd like to keep the budget under $300 a night. Ideally, we'd love a small resort that has some services, has a kitchenette, and is family-friendly. My son will be too young for the large Club Med "kids club" places. A little splash pool or children's pool would be great. But ultimately, we're just looking for a nice place to relax, that will welcome our toddler.

I've found some places in Mexico that look great and reasonable, on Isla Mujeres or Akumal. But how is Mexico in September?

We've also considered a cruise, maybe Disney. We've never been so I'm not sure if we're "cruise people," but the low-hassle nature is very intriguing!

Thanks for any advice!

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