My cousin and her husband have a nice sailboat they take out on the Long Island sound. Have invited me many times...just don't want to be stuck out on that thing for a whole day.
Can't imagine why not. You start the day with Bloody Marys or Mimosas. Smoke a Connie while dropping crabpots. Do a little easy sailing. Pass some charcuterie around for lunch with cold beer. Then you do a little hard-core sailing until it's time for another cigar. Maybe sneak in a nap. Then you retrieve crab pots, sail back to port, and have a cocktail while the crab is boiling. Then you stuff yourself, have another cigar, and go home. Or, in my case, you crash in your berth and do it all again the next day.