To Go or Not to Go: Navigating Winter Choices in Florida

I never thought I'd spend so much time pondering whether I wanted to go to Florida. For years, it was simple. Winter arrived in Canada, and we packed our bags. We headed south and settled into our condo in Florida. Warm weather, sunshine, a few beers, golf, dinner with friends, and maybe a trip to the beach. Then we'd come home when we’d had enough of the heat and were ready for spring. That’s what Canadians have been doing for generations.

But things feel different now. Not necessarily in Florida itself, but in our heads.

I'm a Canadian. I love Canada. However, I don't particularly like what's happening politically between Canada and the United States right now. The tariffs, the insults, and the constant political drama are unsettling. Watching the relationship between our two countries deteriorate feels like witnessing a family argument that has gotten completely out of hand.

But here's my problem: I have friends in Florida. Real friends. People I've known for years. They’ve invited us into their homes, sat around the pool with us, gone out for dinner, and helped us when we needed something. They’re not Donald Trump. They’re Americans. And there’s a difference.

Do I Punish My American Friends for Their President?

That’s the question I keep coming back to. If I don’t go to Florida, what exactly am I accomplishing? Am I sending a message to Washington? Perhaps. Am I hurting the American economy in some microscopic way? Maybe. Am I making some kind of principled Canadian statement? Possibly. But I’m also missing dinner with friends I’ve known for years. I find myself sitting in Canada in February, while it’s -15°C outside, thinking about how I’m supposed to feel morally superior while looking at six inches of snow.

That’s where things get complicated. The Canadian government’s current travel advisory doesn’t label Florida—or the United States generally—as unsafe for Canadians due to the political dispute. As of September 15, 2026, Canada continues to classify the United States at “Take normal security precautions.” That’s worth remembering. Sometimes, the way we talk about the United States in Canada makes it sound as though we’ve entered a hostile foreign country. We haven’t. We’re still neighbours.

But Something Has Changed

I don’t want to pretend nothing has happened. Something has changed. The United States has imposed tariffs on Canadian goods, and Canada has responded with tariffs of its own. The political rhetoric coming out of Washington has been extraordinarily provocative. Canadians have reacted. Some are buying fewer American products. Some businesses are reducing their reliance on American suppliers. Some Canadians have decided they simply don’t want to spend their vacation dollars in the United States.

That isn’t imaginary. Reuters reported in September that Canadians are increasingly pulling away from American products and tourism as the dispute continues, with some travellers choosing Europe instead. I understand it. If someone feels strongly enough about what’s happening that they don’t want to spend their money in America, that’s their decision.

But then I look at my own situation. And I think: Wait a minute. What about the people I know?

Some of Our Friends Have Already Decided They’re Done

This is where I think the senior experience is particularly interesting. We aren’t talking about a two-week vacation. Many Canadian retirees have built part of their lives around going south. They own condos, rent for several months, have American neighbours, belong to golf clubs, and have favourite restaurants. They know the waitress at the local diner. They have friends they’ve known for 10, 15, or even 20 years. For some Canadian snowbirds, Florida isn’t really a foreign country anymore. It’s the place where they spend January.

Now, some of our friends are saying they’re not going back. They don’t feel comfortable. They don’t want to support the United States financially. They don’t want to be somewhere where they feel unwelcome. Others are looking at Portugal, Spain, Greece, or other warmer parts of Europe. I get that too. There’s something appealing about spending a Canadian winter somewhere beautiful while also feeling that you’re putting your vacation dollars somewhere other than the United States.

But Europe isn’t Florida.

Europe Sounds Wonderful Until You Actually Think About It

I love Europe. Give me Lisbon in February, and I’m all ears. But there’s a difference between spending three weeks in Portugal and spending four months in Florida. Florida is easy. We know how everything works. We know where the grocery store is, where the pharmacy is, and where the restaurants are. We know our neighbours and how to get around. We understand the healthcare system. And, perhaps most importantly for people our age, we have friends there.

That’s not something you can replace simply by booking a condo in Spain. You can replace the weather, the palm trees, and the golf. But you can’t necessarily replace 15 years of friendships.

So What Should We Do?

Honestly? I’m not sure there’s one right answer. And maybe that’s the point. I don’t think Canadian seniors need to make this into a moral purity test. You don’t have to decide that America is wonderful. You don’t have to decide that America is terrible. You don’t have to defend Donald Trump or the Canadian government. You don’t have to pretend the trade dispute doesn’t matter. And you don’t have to boycott Florida to prove that you’re Canadian.

You can simply ask yourself a much more personal question: What do I actually want to do with the next 20 winters of my life? That’s a very different question.

Maybe We Don’t Have to Choose Forever

This is where I think many of us may be getting unnecessarily worked up. We don’t have to sell the condo tomorrow. We don’t have to swear we’ll never cross the border again. We also don’t have to blindly carry on as though nothing has happened. We can wait. We can see how things develop. We can spend part of the winter in Florida and perhaps part somewhere else. We can visit our American friends without turning the trip into a political statement. We can explore Europe. We can make our decisions year by year.

That’s actually one of the great advantages of being retired. We have time. We’re not trying to decide where we’re going to spend the next 40 years. We’re deciding where we want to spend January.

And Maybe We Should Remember Who We’re Actually Angry With

This may be the most important part. When I walk into a Florida restaurant and the person serving me is an American, I’m not walking into the Trump administration. When I sit beside an American couple at the pool, I’m not sitting beside the White House. When my American neighbour asks if I’d like to join them for dinner, they’re not asking me to approve of American trade policy. They’re asking me to have dinner.

There’s a temptation, during periods of political tension, to turn countries into single personalities. America becomes Trump. Canada becomes Carney. Suddenly, every American is responsible for everything their president says, while every Canadian is assumed to agree with everything our government does. That’s ridiculous. Countries are made up of millions of individual people. Some Americans love Trump. Some hate him. Some barely think about politics at all. Some probably couldn’t tell you what the latest tariff rate is. And some are just as exhausted by the whole thing as we are.

I’m Also Not Going to Let Politics Ruin My Retirement

This is the part I’m still wrestling with. I don’t want to spend my retirement angry. I don’t want to spend February sitting in Canada, watching the news, and getting increasingly furious about something happening 2,000 kilometres away, while my Florida condo sits empty. But I also don’t want to ignore my own feelings just because Florida has good weather.

So maybe the answer isn’t political. Maybe it’s practical. I’ll ask myself: Do I feel safe going? Right now, Canada’s official advice says to take normal security precautions in the United States. Do I still enjoy being there? That’s something only I can answer. Do I want to see my friends? Absolutely. Does going to Florida conflict with my personal values? That’s a personal question too. And finally: Would I actually be happier somewhere else? That’s probably the question that matters most.

Because if I genuinely don’t enjoy being there anymore, then perhaps it’s time to try somewhere different. But if the only reason I’m staying home is because I’ve spent three hours reading angry headlines about Donald Trump, I’m not sure that’s a particularly good reason to give up a Florida winter.

Maybe It’s Okay to Be Canadian in Florida

There’s something else I’ve realized. I don’t have to become American because I spend the winter in Florida. I’m still Canadian. I can love Canada. I can be angry about American policies. I can disagree with Donald Trump. I can buy Canadian products when I want to. I can support Canadian businesses. And I can still sit in Florida in February with an American friend, have a beer, and complain about the weather. Although, in that particular conversation, I’ll probably complain about the weather in Canada. They’ll win that argument.

So, What Are We Going to Do?

I honestly don’t know yet. Maybe we’ll go to Florida. Maybe we’ll spend less time there. Maybe we’ll spend some time in Europe. Maybe we’ll do all three. What I don’t think I’m going to do is make a permanent decision about my retirement based entirely on the political temperature of September 2026.

Politics changes. Presidents change. Tariffs change. Governments change. Headlines change. Our lives don’t come with unlimited winters. That’s something you understand a little differently when you’re a senior. I’ve reached the point where I don’t want politics deciding where I spend my January. If I decide not to go to Florida, I want it to be because I don’t want to go to Florida anymore. Not because somebody on television told me I shouldn’t.

And if I do go? I’ll still be Canadian. I’ll still have my opinions. I’ll still care about what happens in Canada. And I’ll probably still have dinner with my American friends. Because sometimes the best response to a political argument between two countries is to remember that ordinary people on both sides of the border are still just ordinary people.

And perhaps that’s where I land for now: Keep my Canadian elbows up if I feel they need to be up. Keep my Canadian values intact. Keep an eye on what is actually happening—not every ridiculous thing somebody posts online. And, if I decide to spend February in Florida, keep my blood pressure down and enjoy the sunshine. After all, that’s what retirement was supposed to be about.