Having known sailors that made sailing their vocation, I might not recommend that if you really love sailing. Twigs way of life might be an exception. He (and his wife) built and owns the 50' Alden schooner in the background. Quite often this time of the year, we're in this setting: I'm getting hauled the end of this week, he's leaving the next day bound for Bermuda.
HERON is loaded. Half the cockpit well is full of well lashed, 5 gallon jerry cans of diesel. There could be some good sailing but Twig knows he needs that diesel, he's on a mission. I always wish him luck. He doesn't need any luck, he's a very good sailor and HERON is a boat I wouldn't hesitate to go to the moon with.
Having day chartered all season in Maine, he'll soon be in the Caribbean, doing the same thing. He and his wife and family, have been doing this for nearly 15 years. Their kids are now in the local high school so these days, Twig makes the trip with crew. And their business has evolved so that now they sell spots to charterers for the different legs of the trip - and back in the spring. Smart folks! They built themselves a boat and a career into the HERON.
During my 5 month season - heading in or out of the harbor - I'll pass Twig many, many times. He's always sends a friendly wave even though I know, some days, he'd like to throw all his 'guests' overboard. I get that, my work is service to a large extent and I know how important that is in my work.
But I'm not working in the harbor. This is all fun for me. 5 months is long enough to sail a boat in my leisure time. Roughly 30 days and nights on the water makes me happy. In fact, I've had enough for one season. We spent a lot of timing sailing this year. My diesel gauge is on 3/4 from this season fill up.
My harbor is such a beautiful place, especially in the late fall.