We Stay for Free in Our Caribbean Vacation Homes

With record breaking snowfalls this winter in many parts of North America, my husband Michael and I are betting that many folks are dreaming of escaping to somewhere warm and tropical. Perhaps even dreaming of that vacation home they are going to have someday.

Our “someday” is already here, we have not one, but a series of “vacation homes” to escape to…completely free of charge. Instead of shoveling snow and suffering plummeting temperatures, we are enjoying the sunny warm weather of Mexico’s Yucatán. Between beach walks and cold beers by the pool, we are busy finalizing our travel schedule for the next nine months. Yes, months…not days or weeks…we are spending the next nine months in the Caribbean. We even find it hard to believe, but by housesitting around the world we’ve made it possible.

From Mexico, we head to Barbados and our fifth time in this cute cottage. The miles of pristine beaches, active music scene, and the warm welcome we always receive keep us coming back again and again.

From there it’s a short hop to St. Vincent and our second time in a stunning home perched high on the hillside. From its generous balconies, we overlook the marina below and get a clear view of the sleepy island of Bequia. This quiet haven is our next stop. Here we will be staying in three different ocean-view villas…one of them for the seventh time.

After soaking up the laidback atmosphere of what can only be described as the Caribbean’s quintessential, yet relatively undiscovered, little island, we head off to one of St. Lucia’s famous bays and yet another repeat visit to a three-story villa with sweeping views, infinity pool, and a lush, fruit-filled garden.

Each home is completely different, yet each time we return, we feel like we are coming home. It’s like having a series of vacation homes without the costs of ownership, or of having to air them out and then lock them up again when we leave.

Instead we are picked up on arrival and eagerly catch up with all the news before arriving “home” to warm, often slobbery, welcomes from our four-legged friends. We know the owners, the home, the pets, the garden, and a few of the neighbors too.

Within days we will have been warmly greeted by our favorite vendors, including Elton “the coconut water man” of Bequia and Thomas the friendly St. Lucian Rastafarian, with his woven palm bowls full of mangos and limes. We get to catch up with our friends in each place too. Whether it’s sharing sundowners in Barbados, or the weekly barbeque at Keegan’s on Bequia.

Wherever we are, we are always pleasantly surprised that people remember who we are and the warm “welcome back” we receive.  In fact, some of the full-time residents often comment that we are almost locals now.

Although many dream of having just one vacation home, we must admit, having a series of them instead is hard to beat.

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