Cowgirls and Pirates: My Favorite Day in Nicaragua

I’ve done a fair amount of gushing already about my time in San Juan del Sur. I fell in love with this breezy little beach and surf town, and put aside plenty of time for research — yes, let’s call it research — into all the many ways to keep oneself entertained there.

Yet I have saved the best for last. Not only is what follows the best day I had in San Juan del Sur, it’s one of my favorite memories from this entire trip. And that memory is playing cowgirls and pirates with the crew at Rancho Chilamate.

It all started with the earliest wake up call I had in San Juan del Sur, a 7:30am pickup from the center of town. As I scoured the eerily silent streets for a Diet Coke, I saw a blonde in a cowgirl hat approaching and concluded that my ride had indeed arrived. Despite the early morning hour, Noelani was bubbly and sweet and I quickly felt a Stage Five Friend Crush brewing.

In the twenty minute drive out to the ranch, we discovered a shared affinity for all things aloha (Noelani is a Hawaii native), karaoke, and ocean. As caffeine cleared the cobwebs from my brain, I started to get the feeling it was going to be a great day.

Driving through the gates of Rancho Chilamate, I was greeted like an old friend. Heather, also known as Blue, was so down-to-Earth it took me a moment to register that she was the owner of the beautiful ranch in front of me. And her crew, cowgirls Amanda and Heather and cowboy Nick, were equally disarming in their charm.

I took a grand tour of the property and immediately regretted I wasn’t calling one of the four cozy guestrooms home for a night. Who wouldn’t want to wake up to that pool, or linger over dinner with this crowd?

I arrived at Rancho Chilamate with zero expectations. I knew that their rides were ranked number one on Tripadvisor for things to do in San Juan del Sur and I knew that I loved unique horseback riding experiences, but I hadn’t asked any questions or done any research beyond that.

So imagine my delight when our first order of business was suiting up in a fully stocked cowgirl closet, and doing a photoshoot in front of those gorgeous blue doors.

They had me at dress up time. And professional photographer.

Next, we met our horses. My partner for the day was a beauty named Bruno, who I’d been matched with after answering questions about my personality and riding experience. Our group was perfectly sized — five riding guests and three ranch guides, and we meandered contentedly through dirt roads and wide open valleys towards the beach.

There’s no mane-to-tail riding at Chilamate. The horses moved organically, and I felt connected to Bruno as we tested out different gaits and took turns saying hi to different riders and horses. I realized right then and there I could never go on another stale trail ride again. Not after this.

We crested a ridge in the valley and suddenly, I was staring out at the sea. The horses knew exactly what to do.

At this point, we dismounted and everyone took a break — the horses relaxed in the shade and we toasted to our journey with cervezas and warm goodies baked by women in the local community. It had only been a few hours but I felt like I was surrounded by old friends. When cowgirl Heather revealed it was her birthday, I was genuinely thrilled to be spending it with her.

And then, it was time to really ride.

After a demonstration and a thorough briefing from the cowgirls, I swallowed my nerves and tried something I’d always dreamed of but didn’t know if I’d ever actually do.

Bruno and I galloped down the beach, over and over again.

Running with a horse, and feeling the full power of his speed carry me across the sand, was one of the most exhilarating things I’ve ever done. I felt a white noise of adrenaline coursing through my brain and when we slowed to a trot there was nothing I could do to stop my beaming.

Back at the ranch, I still couldn’t wipe the grin — nor stop babbling about the morning and thanking everyone for such a special experience. Perhaps to keep the momentum going — or perhaps to shut me up, at least temporarily — shots of rum were offered all around.

I’ve been horseback riding all over the world, and I’m grateful to have had some unbelievable rides in places like Iceland and Costa Rica. But I’ve never left the saddle smiling as wide as I did at Rancho Chilamate.

And a big part of what made the morning so special? The people I shared it with. By the time we were throwing back rum shots I was ready to ditch the blog for a pair of cowgirl boots and move myself right to San Juan del Sur. So I think you can imagine my reaction when one of the girls asked me if I had plans for the afternoon, and if not — would I like to join the whole crew on a catamaran cruise?

Um, yes, I think I can clear my schedule of answering emails and filing my nails in order to join the seaside birthday celebrations of one of my newest BFFs and future ranch roommates! It was like I played like the good times lottery and hit the jackpot.

Photo via Adventurous Kate

After a quick stop in town to grab a bikini and Kate — who responded with impressive chill to my frantic “SOS DROP EVERYTHING FORGET WORK WE’RE GOING ON A CATAMARAN SEE YOU IN SEVEN MINUTES” text message — we boarded the appropriately named Must B Crazy and got straight down to quality control testing a few more bottles of rum.

Kate and I had actually been eying up posters for Nica Sail and Surf all week, and had planned to treat ourselves to a day out on the ocean eventually. But we couldn’t have dreamed up a better afternoon to be out there, or a better group to be out there with.

After sailing through the San Juan harbor, we made our way out to a secluded private beach. Tossing a bag of beers overboard, the captain told us to swim to shore and go wild. And wild we went.

Swimming in the turquoise sea, sipping on free-flowing rum drinks, frolicking on the most beautiful beach I’d seen in Nicaragua, and laughing with an amazing group of new friends? I don’t think life gets much better.

But then we got back on the boat, where the captain had prepared fresh ceviche from the fish he’d caught on the way out, plus what appeared to be a bottomless bowl of gourmet guacamole. So actually, it turned out, life could get even better.

As the sun set and we made our way back towards San Juan del Sur, the group starting making a game plan for the night ahead — a night that, unsurprisingly, would be filled with even more good times and great laughs. But me? I was quietly reflecting on the day behind us, confident it was one I’d remember for a very long time.

‘Till next time, San Juan del Sur.

Practical Info

Rides with Rancho Chilamate are $69-79 depending on the time of day. Tour departure times are based on the tides to allow for the largest, flattest beach possible. The total tour lasts five hours, with about three hours in the saddle. Beautiful professional photos are posted on Facebook for free and available at full size sans watermark for purchase. A portion of each ride goes to a community development fund. I received a free ride in order to review it for this site.

Cruises with Nica Sail and Surf cost $75 and last from 1pm to sunset. Beers, Flor de Caña cocktails and snacks (in the form of ceviche, fresh guacamole and chips) are included.

While splurges, both excursions are excellent and clearly, in my opinion, worth every córdoba.