In our home, “winning the internet” means one of us has found a flight from Saint Lucia that we deem not ridiculously expensive. We have quite literally flown through Canada (and saved over $300, overnighting expenses included) to end up in Miami in order to collect our Amazon orders, check on our storage, and binge-eat Chipotle.

Here’s my 16 step guide that accurately sums of the aspects of trying to “win the internet” and book a flight off the rock:


Use Google flights to see what prices are to where you want to go.


Check if it makes a difference to get one way tickets.


Search the actual websites that fly out of your rock: LIAT, Caribbean Air, interCaribbean Airways, Air Sunshine, Air Caraibes, and other regional airlines that don’t come up in Google flights results.


Change your travel dates a little.


Start over because your wifi cut out at a critical point.


Pour yourself something with rum in it because #5 happened.


Repeat steps 1-6 for airports that are sort of close to your destination goal, or at least have cheap connections to it.


Create a spreadsheet of flights and assign points: +1 for each stop, +5 for an overnight layover, -3 if it’s an overnight layover on another favorite rock.


Graph your spreadsheet on a point vs. price axis.


Consider sailing to another rock and using that at your starting point.


Read complaints about airlines losing checked baggage like the one that claimed that LIAT stands for Luggage In Another Town.


Measure your carry on and realize it’s too large for 90% of regional airlines.


Check prices again for anything that scores < 5, was initially within your price range, and can accommodate your new, locally purchased, very tiny carry-on.


Repeat step #6 because obviously your day-long search must have alerted the airline industry to your intentions, so prices have increased by 20%.


Install VPN and pretend you’re searching from within Sweden.


Email your parents and ask if they’d rather come to see you instead.

Flying in the Caribbean

–   –   –

As with most everything on a rock, flying in and out is anything but simple.

Do you have any travel hacks that make coming in and out of your island even slightly more convenient and/or more affordable? What’s your flight booking process like where you are?

Current Rock of Residence:

St. Lucia

Island Girl Since:


Originally Hails From:

Hawaii & Texas

Faced with the choice of using her college degree to find a “career” somewhere on the US mainland or moving to an island, as soon as her tasseled graduation cap hit the ground, she was on her way to Honolulu. A little under a decade later Sara found herself on a press trip in Saint Lucia and hired by a resort there to create destination marketing content and materials. One thing led to another and after too many 24-hour commutes from Hawaii to Saint Lucia + a Trinidadian boyfriend to call her own, she sorted her possessions into “worth the cost of shipping” or not piles and made her way across the Pacific.

Since then, she has created a hospitality & tourism consulting business, Coral Range, that keeps her island hopping, lived on Abaco in the Bahamas for a year, learned to cook everything from bodi to salt fish, and fully embraced the Caribbean lifestyle – though her chipping and wining will always need some work.

Want to read more posts by this writer? Click here.

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