When getting a travel insurance quote from Squaremouth, you can enter up to ten travelers. If the traveling party is larger than ten people, then separate quotes will be necessary. Even with separate policies, some coverage will include traveling companions, which are people sharing the same travel itinerary. The best example is with trip cancellation. One covered reason is when there is a sickness, injury or death to you, your family member, a traveling companion or family member of a traveling companion. Always refer to the certificate of insurance for details.