Check to see what your credit cards or other insurance policies (such as life or health) cover in terms of travel and/or illness while outside the United States or your home area. You might only need to purchase supplemental coverage from another insurer.
When researching companies, seek specifics, and if possible, request a sample (or thorough summary) of the actual policy before you buy. Be sure to read the fine print! If you have questions, make sure they're answered to your satisfaction by a qualified agent.
Be sure to ask if the company has any restrictions on sailing vacations. (Some companies don't cover certain sports-
related travel.) If you have a pre-existing condition, ask if any incident that happens as a result of that condition will be covered while you're traveling.
Ask if the company has a 24/7 hotline help number. If you're faced with a travel or medical issue, this is an excellent service to have.