Originally Posted by emcentar
I don't want to race, I'm not looking to cross oceans - I just want to get out of the city and onto the water with my dog and my wife and a picnic cooler and maybe spend the night outside with a beer in my hand.
I've saved about $15,000, hopefully enough for a little starter boat and a slip for the season.
Take a look at the Catalina 27. Here's the listing from YachtWorld
for the Chesapeake area. It has boats from $4k to $15K with the range of conditions that would suggest. These boats are designed to be used exactly as you described.
Here's the best part. If you really like cruising the bay you can sell the boat in two years for exactly what you paid for it and move up. This will also have more room aboard for family and fido.
The best thing to do is go and look at some boats. That will give you a feel for the differences. Also let people know you're looking. A lot of the boats in this price range aren't listed on YachtWorld. Pick up the Salty Dog, check Craig's List and ask around in marinas. These boats are out there.
And there's no need to settle for something that needs a ton of work. Find a boat that someone loved. It will be much easier on both you and your wallet.
Oh, and don't discount day sailors like the Catalina 22 with a pop-top. They're like little pop-top campers and a lot of fun to sail. Overnighting in them is like camping in a pop-top trailer. And again in two years you can sell it for what you paid - and REALLY nice ones can be had for $5-$6K.