... You will likely be required to demonstrate competency before being allowed to rent a sailboat. Be sure to keep your skills current and be ready to show that you know what you are doing. You can find boat rentals that are complete with captain and crew. These are called charters and are a great way to go if you prefer to skip the work that goes with operating a boat. This is of course an expensive proposition. But it’s also a lot of fun because you are basically going on a private cruise. The sky’s the limit as long as you have the funds to cover it. Something to consider when renting a boat is who will be responsible for damages or injuries. Ask about insurance and what is covered. You will probably be offered insurance as part of the rental agreement. Be sure to accept this because a lot of insurance policies cover the business operator only. Also inspect the boat for any type of damage prior to using it. Point out anything that looks like a problem and get a waiver in-writing that releases you from responsibility for existing damage. ... Boat rentals are a great way to test different boat types and models before making a purchase. You can find most any combination of model and power output as long as you have the time and patience to look around. Even if you can’t locate an exact match, there should be a close enough fit to yield a good test run ...