San Juan del Sur, Nicaragua, is a surfer's paradise. The town is fun and funky, and while it's a little expensive by Central American standards, it's very reasonable for anyone used to North American prices. However, the anchorage is one of the strangest we've ever visited. There are several dozen boats permanently anchored here, even though the south Pacific swell rolls straight in. There are people actively surfing off the beach, and the folks anchored well into the bay could easily surf right off their boats.
While we visited, there were swells over seven feet, and it's mighty disconcerting to be riding these big rollers at anchor, having the whole town (including several multi-story buildings) disappear when you're in the troughs. When the wind blows, you get held stern to the swells and it's reasonably comfortable. When it's calm, though, it was the worst anchorage for rolling we'd ever encountered.
There isn't anywhere good to land a dinghy, but there's a water taxi service that will pick you up and take you back during daylight hours. It costs 50 córdovas per trip, and it's a great deal. The water taxi doesn't have a radio or cell phone, so you stand on your bow waving frantically in its direction when you want a ride. A few times we arranged times to be picked up a day in advance.
While the entrance to the bay is very wide, entering at night would be tricky. There is a green buoy marking the southern edge of the reef on the north side, but the light on it is red, making it look like you should enter between it and the point, which would take you right into the reef. The chart shows range lights, which do exist, but if you followed them, you'd run straight into a large mooring buoy at the edge of the anchorage area. During daylight, however, the bay is easy to enter and there's lots of room to anchor.
The town is very nice, and there's a very friendly community here of locals, ex-pat gringos and surfer tourists. There a several great restaurants and bars, including a bookstore-cum-café (El Gato Negro), a fancy artisan bakery (Pan de Vida, on the road leading to the gas station & out of town) and a real Irish pub complete with Guinness (Casa Irlandia). There are a bunch of great surfing spots nearby, so we have to recommend it as a stop for anyone who wants to catch a wave. The anchorage is safe enough, and the town is nice enough that even non-surfers might want to stop for a day or two.
If we didn't have to wait for an engine part we would have stayed only a couple of days, but we'll be staying at least a week as it is. Like all things in life, San Juan del Sur is a trade-off - a great town with a crummy anchorage.