10 Toughest Bluewater Sail Boats There are boats that can cross oceans, and then there are boats built to survive anything the planet throws at them. I've spent the last three years deep in the sailboat market, researching everything from coastal cruisers to full-on expedition machines. I'm not doing this for Proper Sailor
5 Reasons Not to Live on a Sailboat Living on a sailboat sounds incredible. Wake up to sunrises on the water, explore remote anchorages, live the simple life with minimal expenses. Freedom. That's the dream everyone sells you. Most people who try living on a boat quit within two years. And it's not because Proper Sailor
Why Most People Quit Sailing Here's the dream: You buy a sailboat, quit your job, and sail off into the sunset. Freedom. Adventure. Living your best life. Here's the reality: Within a few years, that same boat is either sitting unused on a trailer, rotting at an abandoned marina, or—if Proper Sailor
How Much Does a Sailboat Cost? Looking for a sailboat is an exciting time, but also daunting. Most times you will see a listing for $30k and think "great, that's within my budget". But that may be your first mistake. The truth is that buying the boat is approximately only half of Proper Sailor
Do You Need Sailing Lessons? Here's what the sailing schools won't tell you: No, you don't need lessons to learn how to sail. Here's what they also won't tell you: You probably should get them anyway. Let me explain. The Legal Reality In the United Proper Sailor
