Like most of the others, we choose to sail, and fortunately we can afford to. I'm doubly fortunate in that my wife also enjoys sailing and cruising, so it's something we plan and do together. In other words, sailing is priceless.
All that being said, ownership of a small trailerable sailboat can be a real bargain compared to other recreational pursuits. A used small cruiser is cheap enough to be bought by most people for cash, and the rest of the costs are similarly downsized. For that, your cruising range is only limited by how far you're willing to drive.
I would estimate that our sailing costs (all purchases, maintenance, insurance, club, consumables, storage) all in, are less than two Starbucks lattés a day. You can reduce costs even further if you can store the boat on your own property.
Small sailboats have incredible bang for the buck, really, and it certainly refutes the common misconception that boating has to be expensive.