I recently heard from a reader who travels from six weeks to three months each winter. He and his wife use miles for airline tickets and stay in a time-share. They've had a difficult time finding travel insurance for these trips, and he wrote to ask me why.

Long trips, airline points, time-shares: These can complicate travel insurance.

The longer a trip, the more difficult it is to find coverage. Still, some plans cover travelers for extended trips, even for durations of up to a year, according to Mike Griffin, director of customer care at InsureMyTrip, a travel insurance comparison site.

"You'll be required to give travel dates when requesting a travel insurance quote," Griffin said. That could be a problem for some snowbirds who leave town with only a vague sense of when they'll return.

Since travel insurance is meant to cover the unexpected, it must be bought ahead of time. "You buy travel insurance several months before your trip because you can't predict the future," said Bob Chambers, vice president of operations for insurance company Generali Global Assistance.

As for airline points, they can't be insured because there is no money involved.

"What you can do is insure any taxes or fees associated with points and miles and include that amount as your trip cost," Griffin wrote in an e-mail.

Finding coverage for time-shares can be trickier. "Generally, insurance companies consider your time-share as more of a secondary home, so it will likely not be a covered expense under most plans," Griffin noted.

"Travelers can insure the pre-paid, nonrefundable value of [a time-share] under Trip Cancellation or Trip Interruption, in case they had to cancel the trip or return home due to a covered event. The only caveat is it can't be a second home that they own," according to Chambers.

No matter the cost, duration or lodging of a trip, travelers are generally able to secure insurance for things like loss of luggage, travel delays and emergency medical coverage, even evacuation.

Anyone taking a long trip may need to shop around and talk to agents to understand what kinds of coverage they can obtain.

Send your questions or tips to Travel Editor Kerri Westenberg at travel@startribune.com, and follow her on Twitter: @kerriwestenberg.