
I get equally excited and frustrated planning a vacation. My quest for perfection always stifles progress and I often spin my wheels more than necessary trying to piece together the perfect overall experience which includes the best flight schedules, ideal hotel, spacious room and plenty to do while we are away. I’m also always on the hunt for a deal, trying to best leverage points and miles to save a couple of dollars in the process. My list of must haves is longer than most and I’ll admit to having high standards, making it difficult to check all the boxes. Add in the fact that we try not to repeat locations and it forces us to look outside the box a little more than normal.
This year, in particular, I mulled over just about every tropical location within 500 miles of the equator for our April family vacation. I stumbled across some lesser known and harder to get to locations in Costa Rica, Mexico and throughout the Caribbean (who knew about Canouan?!). Virgin Gorda in the British Virgin Islands made it to the top of the list and Belize was tempting as well. Then we had a reality check – a lot of the allure of these far-flung destinations are the excursions and local culture that you can experience while you’re there. Ziplining through the jungle, riding ATVs on the beach or taking a catamaran to uninhabited islands for snorkeling sounds amazing, until you realize that your 5- and 7-year-olds will be tagging along (who don’t meet the height/weight requirements to do much of anything!).
Seeing as we checked the Disney box last year, we reevaluated our priorities and set realistic expectations about what we would all enjoy. We would also be traveling during the kid’s school vacation week this year, something we’ve never done to avoid crowds – making the off-the-beaten path locations even more attractive. As we eliminated each location for its own reason (too hard to get to, no good flight times, too expensive, etc.) all fingers started to point to the same location: Anguilla. It’s a place we fell in love with last year and have talked about on nearly a daily basis since we came home. It is my happy place.
Even though going for round two may violate my ‘don’t repeat locations’ rule (which is really more of a suggestion), it won out in virtually every other way. The kids were excited, too. They can’t wait to see Miss Jackie by the pool, go snorkeling or drive a Moke around the island. After last time, I felt like there was still more to explore, restaurants to eat at and sunsets to drool over. Looks like we’ll now get our chance!
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