He captains his 1899 friendship sloop and normally does three trips a day, seven days a week. The boat is holding up very well. Every Spring he spends about 3 weeks working on the boat to get it ready. That always includes a complete paint job and replacing a few bits of wood. He actually tends to have to do more work on his 70s vintage fiberglass friendship sloop than on the woody. His third boat is a lobsterboat fitted out to carry passengers. It gets more beat up than the sailboats for two reasons. First he hires captains to run the boat and they don't seem to "care" about the boat as much as he does. Second they haul lobster traps as part of the tour and that is rough on the boat even though they only have 5 traps to haul.

I have other friends who chartered their sailboat as a bareboat for many years. The boat definitely got some wear and tear, particularly in the first few years. After that they got a lot of repeat charters and the boat fared better. Bare boat chartering worked for them because they lived a ways from the boat and only used it about 2 weeks a year. The boat was professionally maintained during the charter and off seasons and always looked great. Of course, the bones of the boat were good, which likely counted for a lot.