From Brandon to the Turks and Caicos Islands $524
Grace Bay beach in the Turks and Caicos islands is heaven on earth. It's where white, soft sand meets the glorious turquoise ocean water.
I describe the little known island, as "first world caribbean." I say this because, workers are paid a living wage and there is plenty of work. The food quality is of north american standard, and as a tourist you can walk around safely and without worry. The resorts are not gated. They are also not massive in size, like some in Mexico. Rather, I liken it to Hawaii. It's a safe, relaxed area, where accommodations are almost always condominiums rather than resorts or mega-hotels. Again, similar to Hawaii, your rental accommodation will have a kitchen and you can save money preparing your own meals.
There is only one resort on the island that is indeed massive and all-inclusive. It's Beaches family resort. (The family-friendly version of the Sandals chain.)
Grace Bay beach is a small area, just a few miles and you can comfortably walk the whole beach at sunset.
You will do well to stay at any resort on Grace Bay beach. I have personal experience with Ocean Club and the Royal West Indies condominiums. Both are mid-range in price, well kept, and ideally located.
If you haven't heard the stories of how the Turk and Caicos wanted to join Canada, you should google it. (Oh, how I wish they were a Canadian territory!) Regardless of their commonwealth affiliations, they have welcomed many Canadian businesses and you will be quite surprised at how "Canadian" this island feels. Drive past the Napa Auto Parts store, and the Home Hardware you could stop at Scotiabank on your way to IGA to pick up groceries.
You might also be surprised to learn that you can get a return flight with Westjet, from Brandon for $524. Yes, that includes taxes. Hotel/condo rental is extra.
A great price from Winnipeg, is about $485.
Packages can often be found at $1200-1500 per person.
However, if you plan to go at Christmas, or Spring Break, expect to pay three times that price.
Definitely one of my favourite destinations, and almost always listed as one of the top 10 beaches on earth, regardless of the publication or author.