In a word, YES. The differences are tremendous. One thing-if you take the cruise line insurance, and book anything on your own-hotel, air, shore excursions, rental car, it is NOT covered. Cruise line insurance will only cover what is booked through the cruise line (and that is generally a VERY expensive way to go). Take a look at this link http://www.insuremytrip.com/

There are many types of insurance and you must pick what is best for you. Don't forget about things like evacuation. From a ship (or on land) in the Caribbean could easily run $25,000. And NO, you probably won't need it, BUT what if you were involved in an auto accident? Everyone always thinks MAJOR medical problem like a heart attack. But a snorkeling accident, jet ski accident, or auto accident could be just as disabling and maybe even more expensive.

After you look at the link and still have questions, feel free to email or PM me. I buy trip insurance about 6 times a year, including at least 2 cruises and have read EVERY one of the policies including the fine print.