$ave with Travel Insurance

I've been fortunate enough to travel to 38 different countries, and I can't tell you the number of times I've been asked to buy travel insurance.  While I always invest in this for more expensive trips, I never buy directly through the company I booked the tour, air travel or cruise.  Why?  They charge a premium on the exact same thing you can buy more cheaply yourself. (Honestly, sometimes their policies are worse. Priceline, for example, only gives you a few "covered" reasons for trip cancellation/delay. Ridiculous.) I've personally had experience with Allianz, but other agencies offer similar travel insurance plans for roughly the same cost, such as through Costco.  If you're really curious, next time you book a vacation, ask how much the travel insurance costs and through which insurance company.  Then try pricing the same amount of coverage directly with that insurance company yourself.  You'll likely be pleasently surprised at how much you save! 

Another tip when buying insurance - some companies automatically include your airfare, so you don't need to add that into the amount of insurance you're buying.  I've also noticed pricing often changes in $500 increments, meaning when they ask for your total trip non-refundable cost, if you input $1500 versus $1501, there is a big difference in price.  As an example, if a trip is $1300, I recommend checking out the pricing by imputing both $1300 and $1500 and if the cost for insurance is the same, get coverage for $1500!  You never know what additional non-refundable expenses you'll have on top of the base trip cost.

My travel buddy's missed flight almost meant a
missed Caribbean cruise for us both, but thanks to travel
insurance we were relaxing on the beach in no time!

In addition, you might not even need to purchase travel insurance, but still be covered.  How?  Many credit cards offer similar benefits.  They sometimes cover car rental insurance (above and beyond whatever your own car insurance covers) - saving you the wallet-ache of adding on extra insurance at the car rental agency, yet allowing you to still have peace of mind.  Additionally, baggage loss/delay, and even trip interruption/cancelation (typically with the travel specific credit cards) is sometimes included.  I'd recommend calling to check these options before you decide to book travel insurance.