If I plan my trip myself, may I still buy travel insurance? Published by Chris Harvey January 15, 2008 Yes, you may still purchase travel insurance if you make your own travel arrangements. Related articles: Can I get live assistance with a quote or purchase? Are there medical conditions that are not covered by travel insurance? Should I consider extending my return date to accomodate any unforseen delays in my return home? Does TravelSafe cover my frequent flier miles? Do any policies cover trip cancellation/trip interruption as a result of work related reason or business commitments?