If you're planning a big North America trip, we should warn you this continent is massive. And depending on what time of year you go, you might have a ton of different climates and activities and really each of the big three countries need years to explore on their own.
You're best off deciding when you want to visit and what you want to do before you start booking hotels. If it's beaches and water sports you want, we'd look down south towards Florida or California and then into Mexico or really any of the Caribbean countries. If you want skiing and winter sports, then look up north towards Canadian spots like Mont Tremblant or at least upstate New York, Utah, or any of the states that have great mountains and see snow!
Really with such a large continent, you're guaranteed to almost always find something to do.
Click the Map to jump to a country