A good problem to have
Sounds pretty swanky until you figure out how much work it is... even if you hire some of it out.
We have a beach house and a boat, there is a buoy at the beach house to accommodate the boat, but more recently the boat has come to live in town in a slip where I get to use it more - then I get up to the beach house and miss the sailboat. But then there's a Whaler in the boathouse, a couple of dinghy's and a whole fleet of kayaks and I start to wonder if I have a problem, or if I'm just trying to store my money somewhere where I get some interest in the result.
But (recent experience aside) houses appreciate while boats depreciate. Actually, in my limited experience, you sell boats for exactly the dollar figure you paid for it, regardless of how long you own it or what inflation does - and after inflation, you take a real loss. But that assumes you purchase boats wisely and keep them for a long time. So the beach house is a much smarter thing to have. So don't tell my spousal unit, but I want *another* boat. Not a different one, another one. You see my spouse tolerates the boat(s) but she loves the beach house, and the argument is we will sell the city house one day and retire to the island and it will all work out. With my boat on the buoy of course.
To more clearly answer the question - we spend the fourth of July week at the beach house, we take two weeks each summer for a cruise, and we go to the beach house any weekend when there is not a reason to be in town. This spring sail races have been a reason to stay in town. Next two weeks, no races - we go to the beach house. What do I do there - I work on the beach house, which, luckily, is part of the fun. If you don't like working on houses and boats, don't get a cottage *or* a boat.