I would use this to get around: Shuttle. Navigating the town itself is easy on foot, but you’ll need hired transport to get to any of the surrounding surf beaches. Most places offer organized tours and ride-shares to popular destinations in the vicinity and my experience was that these were better options than renting a car or paying for a cab.
I would stay here: If you’re going to San Juan del Sur, chances are amazing that you’re there to surf. And so, the spot with the most convenient shuttles and surfboard rentals is definitely Casa Oro. They offer tons of services for tourists, even the non-surfing ones, and have a great location by the market in the heart of town. There’s a shared kitchen for those on a budget and the common areas are decent. It’s got a great atmosphere and seems like a sweet spot to stay. I didn’t actually stay there myself because it was full when we arrived sans reservation – further proof of its good reputation – but I have friends who did and they thought it was swell. (Get it? Swell? Surfing? Ahhh, puns.) If you’re not into backpacker hostels and are looking for something a bit more upscale I don’t really know what to tell you. I’m sure they exist, but I’ve got nothing in the way of recommendations or even educated guesses. Maybe try Google? I don’t know. Good luck.
I would eat here: El Colibri. Easily the best food I had in Nicaragua, it’s got a menu full of local ingredients and tasty combinations that inspire sharing and/or stealing between neighbours’ plates. The list of wines and cocktails is equally impressive and the deserts, devine. If you don’t heed to a single other piece of advice on this page, do yourself a solid and set aside some dinero for a night at El Colibri. To grab lunch on the go, hit up the Taco Stop for the best fish tacos in town. Of course, the market has a fine selection of local produce and a couple of small comidas where you can get a little rice, beans and meat action for less than just about anything else I can think of right now. El Gato Negro has great coffee and baked goods, as well as a fantastic used book store and little gift shop, and Banana Hammocks offer ultra-delicious smoothies with creative flavour combinations that make strawberries and bananas look like a couple of chumps.
I would drink here: Apparently, the hot spot is Iguana Beach Bar. They have ladies’ night specials and dance music and all sorts of other stuff that’s hip with the young people. I’m not really either of those things – hip or young – so I prefer wild and crazy evenings that involve playing Desmoche, drinking vending machine beer and going to bed early and sober enough that I can get up without swearing the next day.
I would do this: Surf. Obviously. It’s what San Juan is known for and it’s no small wonder. There are breaks all over the place to suit a wide variety of levels and experience. Going to San Juan del Sur and not surfing would be like going to Disney World and not getting your photo taken with Mickey Mouse. More or less. Depending on time of year, there’s also a natural reserve not far from town called La Flor that boasts one of the world’s largest populations of Olive Riddley sea turtles. They come several times a year to lay eggs by the thousands and so, if you time your visit just right, you can witness the phenomenon in action. Other popular touristy activities include deep sea fishing, diving/snorkeling and sailing around on a boat drinking beer and flirting with most of Europe and Australia. The best thing I did while in San Juan del Sur, besides surfing, was take a yoga class at Zen Yoga. The studio is gorgeous, the instructors are fabulous and the class itself was one of the best I’ve ever attended. If you can, take an evening class as the sun is setting over the bay. If that doesn’t get your ohm going, nothing will.
I wouldn’t do this: Take valuables to the beach. All you need is a towel and some sunscreen so leave the rest of your belongings stowed in whatever locker or safe situation you’ve got going on at your hostel/hotel. Sticky fingers abound in these tourist hotspots.