Canadians need to think about travelling to countries like Jamaica that condone homophobia. By doing so you are essentially supporting discrimination and persecution through your tourist dollars... good times! The hypocrisy is that the same liberal Canadians who are 'outraged' by the perceived human rights violations of the Harper Conservatives will blindly overlook these issues in the pursuit of a February tan and some ganja. It would be fantastic to be able to travel to a warm and sunny yet tolerant and safe Caribbean destination where Canadian laws and values prevail. Call me a xenophobe but it would be a nice option and a progressive one for the region.
By no means is that hipocrisy limited to the Left when it comes to travel choices. I'm sure there are more than a few conservatives who were outraged at Dion's deal with the "socialists" who'd happily take a vacation in Cuba. In either case, I see this as one of the problems with resort-based vacations. You get a very limited and often staged idea of the local culture, government policies, etc.
That said, you can't expect people to make vacation choices solely on moral issues - everyone would end up with very very little selection in destinations. For example, I don't agree with the Turkish government's heavy-handed approach to Kurdistan or their denial of the Armenian genocide, but I'd still love to visit that country some day. As a gay man, I probably won't ever visit Jamaica or some of the other more homophobic nations of the world (at least until they change), but I'm not going to hold it against anyone who decides to vacation there.
When it comes to the Turks and Caicos, I don't know how gay-friendly the local population is, but I would be cautious with the idea that becoming part of Canada would change their values somehow. The laws might change, yes, but a cultural shift does not happen over night.
I wonder though if people are really motivated to do this for the right reason. Is this an example of Canadian expansionism or is it perhaps a demonstration of our inclusiveness and hospitality? I assume the truth, as it usually does, lies somewhere in between. If we are going to dump all of our historical and cultural baggage on to them, will we take up any of theirs? For example, will school children in Ontario learn about the history of slavery in the Turks and Caicos, and if so, will they learn about it as a domestic issue?