A Holy Battle of the Saints – St. Maarten or St. Thomas

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It’s finally come down to decision time for our annual Thanksgiving trip and the two (well, two and a half) finalists are St. Thomas in the US Virgin Islands or St. Maarten/Anguilla. While our last trip to the Caribbean was a combo St. Maarten/Anguilla trip and we’ve never visited the same place back to back, the appeal of this trip is something our group of friends is finding hard to top. The condo location right on the beach in Simpson Bay with a full kitchen, dining and shopping within walking distance and of course the opportunity to visit Anguilla for a few days at the start provide a nicely wrapped package that makes the urge to resist opening it again rather difficult.

st. martin, caribbean

On the other side, St. Thomas is soooo convenient (inexpensive nonstop flights out of O’Hare) with the fact that we wouldn’t have to mess with US Customs almost a clincher in and of itself. Add to that the close proximity of the resort to the airport for maximum beach time, St. John and the British Virgin Islands being just a ferry ride away and a few beach bars (something the St. Maarten condo resort is surprisingly lacking) to belly up to and St. Thomas has declared itself a contender.


At the end of the day, you can’t go wrong with either destination and it’s nice to have these “problems” to resolve. For all of us lucky enough to travel to our favorite beach destinations, the aforementioned “dilemma” is something we should all feel blessed to have.

So, which one would you choose – St. Thomas or St. Maarten?

Author: Tom W.

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  1. We will be on St. John for Thanksgiving, so that is my choice! If you choose St. Thomas, you know you still have to clear U.S. Customs in St. Thomas prior to leaving??? It’s pretty painless and beats having to do so back in the U.S. proper. Both islands sound wonderful for a Thanksgiving trip. You really can’t go wrong.

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    • Karen, thanks for the info! I had no idea about clearing customs in St. Thomas but anything has to be better than going through it in Miami. Sounds like it might be time to apply for that Global Entry status! Have fun in St. John and maybe we’ll run into each other at a beach bar in Cruz Bay. Cheers!


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