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If you were to think about large-scale efforts – mapping the human genome, searching for monster prime numbers, developing the TESLA, you would be wise to add planning a family Caribbean vacation to your list.

There’s the organizing, packing, passport-checking, last-minute snack shopping, the rounding up of coloring books, crayons, headphones, medication, sunscreen and whatever sand-caked plastic shovels that can be found from the last vacation.

Rodney imposed house rules against me asking him to exfoliate my back and apply sunless tanner the night before a trip, so now I leave that job to the professionals. Which of course never gets done. Time, who? what?

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This year I got my act together and scheduled an appointment that I promised I wouldn’t break. I stuck to my guns, shed my clothes in front of a woman whose name sounded like Mary but wasn’t, and stepped into the booth. After a few passes of her spray gun, she declared that I looked “owa-some” and I skipped back home, a burnished shade of bronze.

My kids weren’t impressed. Over the sobs of one child, another demanded to know what happened to my “other skin”. The third was found later, hiding in a closet. This pre-tan effort, I imagine, won’t happen again.

It was the least I could do to get ready for what promised to be the trip of a lifetime.

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When traveling with kids, Rodney and I have always leaned towards big hotels with big pools, big restaurants, and a bigger set of amenities. The kind of place where a kid can race around and find plenty of entertainment.

This year though, we booked our trip through Inspirato. After looking through their list of properties, we found a house that seemed like it would be a great fit for our family: our own pool, an empty beach, ocean-facing bedrooms, and the icing on our Tortuga rum cake….a well-stocked kitchen.

I’m not sure how many times the word “idyllic” was dropped into the conversation during our stay, but I’m pretty certain that were in three-digit territory.

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Secluded on the South Sound of Grand Cayman, the house was perched above a rocky section of beach that offered hours of splashing, crab hunting, and the ultimate in sunset watching.

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Pristine white sand beaches lay to both the right- and left-hand side of our rocky cove. The waves were big enough to attract a few surfers and stand-up-paddle boarders, whom we watched as we sipped our morning coffee. 

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Every Inspirato rental comes with a destination concierge and our helpful contact Bronwen pointed us in the direction of the dolphin swim/stingray excursion.

The stingrays congregate on a shallow sandbar 30 minutes from shore, which attracts the cruise ship crowd in droves. Had I known that Stingray City is such a raging party, I would have brought a boom box, some local rum and a set of maracas. Local tip: if you want to visit the rays, go in the afternoon.

Despite the crowds, we had a great time and the kids had some memory-making moments as they reached down to pet the rays at their feet.

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Sam wanted to swim with the dolphins, so Rodney took him for a one-on-one session. After giving a quick talk about dolphin behavior, the trainer opened it up to questions. Sam’s first question in a Proustian-length set was whether the dolphins could read.

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On the topic of animals, I have to mention our visit to a family park just south of our property, which was rumored to be full of iguanas. Bronwen suggested that we bring lots of bread to feed the iguanas but didn’t mention that we’d have a hard time making it past the chickens! This little corner of the universe would have been Tippi Hedren’s worst nightmare but we thought it was pretty spectacular.

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Lauren jumped right into the mix, feeding the birds as they flocked to her side. Emma pretended to be comfortable with the situation before needing an emergency exit back to the car. I was in awe of the whole situation – the colors, the plumage, the racket! Rodney, ever-pragmatic, suggested that we get back to the house before we wound up with avian flu.

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Though we traveled to other parts of the island, the pool was our true home for the week. For hours on end, the kids practiced their flips, blasted each other with water guns, and demanded porpoise rides from a more-than-willing grandparent.

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Emma set up a store on a pink raft and decided to sell my hat, a frisbee, a pair of goggles and her TOMS water shoes which she was hawking for the low low price of 15 coins. Meanwhile, Lauren stole my GoPro and practiced the art of the underwater selfie.

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We did all of this pool time at the expense of lunch, which played second fiddle to our daily breakfast and dinner, prepared by our local cook, Rosie Parris. Rosie was on-site to help in the kitchen and give me a well-needed break.

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Of course I used every empty kitchen opportunity to make breakfast burritos, quesadillas, and herb- and spice-infused simple syrups for cocktail hour. I even hauled out my coffee grinder to make some TOMS Honduras blend morning brew with my travel-sized pour-over coffeemaker. Someone please banish me to the land of food snobbery where I’ll live out my years surrounded by glass carafes and the smell of freshly-roasted beans. 

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And let’s not talk about the incident with the vodka.

Scratch that, let’s discuss. I’d infused a handle of vodka with mango, basil and habanero chilies and made the mistake of pouring it into a glass pitcher. Not a mistake per se – let’s call it false advertising since it wasn’t a cocktail but the booze that you’d use to build a cocktail. That subtle reference was lost on my dad who accidentally poured himself a big glass of booze, drank it, and promptly “fell asleep” at the dinner table.

Which, for a kid, is better than Disney. Papa was poked, prodded and decorated with local island flowers. A stuffed bear was wedged into his armpit and a juice box balanced on his forearm. 

Photographic evidence was taken but is now, wisely, sitting at the bottom of my virtual trash basket.

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It was a great trip. Unforgettable in so many ways. From our villa and the food to our TOMS shoes, brand spankin’ just for the occasion.

It wouldn’t be fair to keep all the fun just for ourselves so I’ve partnered with TOMS to host another giveaway for a $250 TOMS gift card.

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There are a number of ways to enter, just follow the Rafflecopter link below:

AND WE HAVE A WINNER! Congrats Debb F! You’ve been sent an email with more details.

Thank you to everyone who participated!

a Rafflecopter giveaway

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The prize, as well as all of the comfortable + stylish footwear that you see in the post was provided by TOMS (excluding the flip flops!). All opinions are my own.

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Details

One lucky reader will win this $250 USD TOMS gift card.

This giveaway is open to US residents only and will end at midnight on 5/03/2014. (11:59PM EST)

We will choose the winner at random using Rafflecopter. We will contact you via email and you will have 48 hours to respond with your contact information or we will have to choose a new winner.

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Further, for purposes of clarity, in no event shall Administrator state or imply in any manner that Company endorses, sponsors, or is affiliated with the Sweepstakes other than to provide the Prize.

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