Does This Marina Slip Make My Stern Look Fat?

Before Casstaway, the total of my time behind the wheel of a sailboat was during our ASA sailing classes (where I was constantly freaking out) and about three minutes during one of our charter vacations when I quickly decided I liked my sailing buddies much better when they weren’t yelling directions at me, and promptly relinquished the helm in favor of more forgiving duties like making...