If you ever get to meet The Traveling Professor, he will constantly brag about how he is considered to be a travel expert by The New York Times.  See this New York Times article.  Seriously folks, listen to The Professor's advice on how to get the most valuable travel information for free.

• Trip Cancellation:  Get the cost of the trip refunded if it is cancelled.
• Trip Interruption:  If a trip is delayed due to weather, lost passport, transportation delays, reimbursement can be made.
• Emergency Medical/Dental Coverage: Since most domestic medical coverage including medicare, is not available overseas, this is especially important if traveling abroad.
• Baggage Delay/Lost Luggage/Change Fee Coverage/Rental Car Coverage, etc.:  All this can be covered free.

The best way to get free travel insurance coverage is to have the right credit card.  I recommend:

Barclay Card:   This is my favorite card for trip insurance.   See the benefits here.  This card has the lowest annual fee of the 3 cards mentioned here.

MasterCard World Elite:  Another one of my favorites. When I was delayed in Philadelphia, the insurance provided by the card paid for my overnight hotel bill and meals.  It has a stiff fee of $450 annually but it comes with American Airlines Admiral's Club membership.  The $450 fee paid for itself.  Here are the travel insurance benefits, some of the best to be found.

Chase Sapphire Reserve:  The mother of all travel credit cards, but with a $450 annual fee (easily outweighed by the $300 travel credit plus points earnings) it is easily worth it.  Here are the insurance benefits.

So, all three cards do have fees but just they will be practically cancelled by the benefit of not having to purchase travel insurance.