You absolutely can buy travel insurance after booking your trip. However, it's always best to purchase insurance as early in the process as possible. If you procrastinate, you may miss out on certain benefits.
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If you would lose the money you paid for your flights, accommodations, rental car, or activities if you had to cancel or go home early, travel insurance that specifically includes trip cancellation and trip interruption is probably a good idea.
In most situations, Medicare won't pay for health care or supplies you get outside the U.S. The term “outside the U.S.” means anywhere other than the 50 states of the U.S., the District of Columbia, Puerto Rico, the U.S. Virgin Islands, Guam, American Samoa, and the Northern Mariana Islands.