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Sailing on a “Pirate Ship” with Two Guys Adventures

I have always said, “A day on the water is better than any day on land”.  It doesn’t matter if it’s fishing or sailing, any day on the ocean is memorable.

In Nica Now Sails with Two Guys Adventures

– Two Guys Adventures Sunset Cruise: San Juan del Sur, Nicaragua – (Photo Credit: Two Guys Adventures)

With three friends celebrating birthdays and two friends leaving Nicaragua we had plenty of reason to bring a group together for a special day. We decided to charter the Two Guys Adventures Pirate Ship.


This massive 3 bedroom, 2 bathroom 50-foot luxury sailing yacht has capacity for up to 30 guests. With just 25 in our group, we had plenty of space to stretch out and relax.

– Two Guys Adventures Sunset Cruise: San Juan del Sur, Nicaragua


Owners Joey and Kelsey are great hosts and really know how to show you a good time. Kelsey wears a devious little grin as she serves round after round of her famous “pirate grog”. 

- The hostess with the mostess.

– Kelsey Coleman, hostess extraordinaire!

And Joey has definitely mastered the art of the sailboat selfie!

Saling in San Juan: Two Guys Adventures

– Two Guys Adventures Sunset Cruise: San Juan del Sur, Nicaragua (Photo Credit: Two Guys Adventures)


We left the port in San Juan shortly after 1 pm and sailed to the private white sand beach known of Playa Blanca.

Here there was lots of time for swimming, snorkeling and walking the beach.

Playa Blanca: San Juan del Sur, Nicaragua

– Two Guys Adventures Sunset Cruise: Playa Blanca, San Juan del Sur, Nicaragua

First mate, Victor expertly “jetisoned” ice cold Toñas out to us as we floated around in the warm crystal clear water. Kelsey’s delicious ceviche made an appearance about this time as well.

When you get a large group of your good friends together on the water with nothing but sunny skies, warm winds and good conversation it brings you back to why you came here in the first place — to spend the highest quality time with the people you want to share it with.

Sunset Cruise: Two Guys Adventures

– Two Guys Adventures Sunset Cruise: San Juan del Sur, Nicaragua

As you can well imagine after a few hours of sailing, swimming and drinking the ride back home was full of joking, laughing and dancing. 

Sailing: Two Guys Adventures, San Juan del Sur, Nicaragua

– Birthday girl getting her groove on. (PHOTO CREDIT: Two Guys Adventures)

The one picture I couldn’t post was the team “full moon” pose. It was taken during the day, so it isn’t tough to imagine the moons on display.

We arrived back in the bay of San Juan just as the sun was setting.  None of us were ready for the day to end, which was clearly a sign of a great adventure! Maybe next time we can do an overnighter?

- Photo Credit: Two Guys Adventures

– Two Guys Adventures Sunset Cruise: San Juan del Sur, Nicaragua (Photo Credit: Two Guys Adventures)

San Juan del Sur’s favorite excursion that Jerry Seinfeld had all wrong.

Since the Two Guys Adventures luxury pirate ship wasn’t sailing during Jerry’s rein I guess he can’t be blamed for his famous line, “I don’t want to be a pirate.”



Two Guys Adventures
(505) 7546-3070

123 Pirate Boulevard 
San Juan del Sur, Nicaragua

Sunset Cruise
$85 USD per person

To check availability and make a reservation email

El Castillo: Río San Juan, Nicaragua

It’s always exciting for us to explore a region of Nicaragua we’ve never visited before.

Elisha’s parents were visiting from the East Coast of Canada. It was their forth visit to Nicaragua and they were excited to embark on a new adventure. Word of a newly paved road to the Río San Juan was enough to cement our decision.

El Castillo: Río San Juan, Nicaragua

– Family adventures and fun on the Río San Juan

The drive to Tipitapa is very familiar to us, as it is on the way to the airport, but this was our first time making the turn east toward the back side of Lake Nicaragua. The newly paved road extending all the way to San Carlos cuts driving time from ten hours to only four. 

The port town of San Carlos is located directly on the mouth of the Río San Juan and the shore of Lake Nicaragua. The town itself is unremarkable, and for us, it was just a place to park our truck and catch a ferry down the river.

El Castillo: Río San Juan, Nicaragua

– Most travelers burn their San Carlos hours by planning river and island adventures and checking emails one last time before they drop off-grid for a while

We parked our truck in the government operated ferry lot. The cost for parking was $2 per day.

There are two ways to travel along the Río San Juan. The fast ferry or the slow boat. We opted for the fast ferry. Our tickets cost $6 per person for the 1.5 hour trip to the town of El Castillo. The slow boat, although nearly half the price, takes twice as long.

El Castillo, Río San Juan

– Fast ferry: Río San Juan, Nicaragua

Our boat passed by small homesteads with herds of cattle grazing on the river banks. We made a fews stops along the way to drop off passengers and supplies to the homes on the river — a reminder to us that there are no roads in this region and that the river is truly the life blood of the people there.

El Castillo, Río San Juan

– Home on the river’s edge: Río San Juan, Nicaragua

The hour and a half trip on calm, flat, slow moving waters was both relaxing and exhilarating. We enjoyed the ride down river so much that the slow ferry might be our choice next time.

El Castillo: Río San Juan, Nicaragua

– Storks, herons, ducks, woodpeckers, kingfishers and dozens of other bird species unfamiliar to us were seen by the hundreds

The charming riverside town of El Castillo

El Castillo: Río San Juan, Nicaragua

– Ferry dock in El Castillo: Río San Juan, Nicaragua

Upon arrival in El Castillo time seemed to slow. We wandered down the main road (which is actually just a wide cobblestone sidewalk) looking for a place to lay our heads for the next couple of nights.

El Castillo, Rio San Juan

– The main “road”: El Castillo, Río San Juan, Nicaragua

After checking out a handful of places we came to Hotel Victoria.

Hotel Victoria looked grand and we expected the room rates to match. Although rooms in the newly built section of the hotel were in the $60 price range, we were pleasantly surprised to find out that the smaller rooms in the original building were half that.

All rooms at Hotel Victoria are equipped with hot water, AC and TV. Breakfast is also included in the room rate. 

El Castillo: Rio San Juan, Nicaragua

– Hotel Victoria: El Castillo, Río San Juan, Nicaragua

Hotel Victoria sits directly on the river’s edge with abundant balcony space and plenty of hammocks and rocking chairs to relax in. From the restaurant you can sit and watch the daily river lifestyle float by. 

El Castillo: Río San Juan, Nicaragua

– Small pangas, row boats, kayaks and old school dugout canoes come and go on the Río San Juan, often providing the catch of the day

El Castillo: Rio San Juan, Nicaragua

– Dugout canoes are often used as a mode of transportation on the Río San Juan

El Castillo is a small village without any roads or cars. In fact, the town is so small bicycles aren’t even commonplace.

The residents of El Castillo have been neighbors (in the true sense of the word) for generations. Everyone we met was friendly and accepting, in a relaxed way, that didn’t show much fuss. Maggie ran around off leash the entire time we were there. By day two many locals knew her by name and often called her over to visit.

El Castillo, Río San Juan, Nicaragua

– El Castillo: Río San Juan, Nicaragua

There are few dining options in El Castillo. The best and most popular restaurant is Borders Cafe.

The friendly, flamboyant owner Yamil serves up some of the tastiest pasta dishes we’ve had in Nicaragua. He uses fresh fruits and vegetables grown from his very own garden.

His beers are the coldest I have ever tasted. How Yamil is able to get each bottle of beer completely frosted over without freezing the contents has left me perplexed.

El Castillo, Rio San Juan

– Elisha & Maggie making friends with the locals at Borders Cafe

What to see and do on the Río San Juan

On top of the hill overlooking the town and the river sits the Fortress of the Immaculate Conception.

El Castillo de la Inmaculada Concepción was built to protect the waterway against pirates, as well as opposing forces like the British. A self guided tour of the fort costs just a couple of dollars, with $1 extra for cameras. The views alone are worth the price of admission.

Nena Tours is the most popular and well established tour company in town. Fishing, kayaking, canoeing and caiman observation tours are available. Nena Tours also offers overnight camping excursions where you sleep in hammocks over platforms built in the trees.

They have English speaking guides and the tours are very reasonably priced. 

Indio Maíz Biological Reserve

Our chosen tour totaled $79 for the four of us, with no extra charge for Maggie. With some locally sourced fruit, snacks and wine we hopped aboard our panga (small boat) with a guide and captain en route to Indio Maíz Biological Reserve.

A few meters up the river we checked in at the park warden’s office where we were greeted by a baby ocelot. This 16-week old rescue cat who had been named Bartola, was already bigger and undoubtedly more fierce than Maggie and tried relentlessly to capture her.

El Castillo: Rio San Juan, Nicaragua

– Maggie’s arch enemy

In the reserve you have a chance to see howler, spider and capuchin monkeys, sloths, caiman (small crocodiles) and hundreds of species of birds. Some hikers have even spotted species of wild cats, including jaguars.

On our hike we sampled sap from a tree that was a natural gum and helped with intestinal troubles. We also sampled a plant that is used as a natural anesthetic. Chewing on a tiny bit of leaf made by whole mouth go numb…for nearly twenty minutes. 

By the time we returned to our boat we had seen (and tasted) enough of the rainforest. Sticky with sweat we were ready for some refreshment and a cool off. As we headed towards the swimming hole we spotted a couple of caiman floating in the river. 

El Castillo: Rio San Juan, Nicaragua

– Caiman spotting on the Río San Juan

100 meters around the bend is where we came to a stop.

We looked at each other with trepidation. Swimmng in the river…with caiman so close?

Too hot and thirsty to worry much about personal safety, and a guide’s promise to keep watch, we waded into the water with plastic cups full of wine. 

El Castillo: Rio San Juan, Nicaragua

Cooling off in the Río San Juan

For many visitors of the Río San Juan the big draw is the world class fishing. There are a handful of lodges on the river that specialize in trophy fishing for the huge tarpon and snook that are prevalent in the waters there.

Fishing regulations on this river are well policed, so if you plan on fishing on the Río San Juan it’s important to book your excursion a week to a few days in advance to allow time for your guide to secure the necessary permits.

El Castillo: Río San Juan, Nicaragua

– Photo courtesy of Rio Indio Lodge

El Castillo is a quaint little town that makes you feel at home within minutes of stepping off the boat. The region has the infrastructure for tourism, but it really hasn’t arrived yet. The locals are not jaded or opportunistic when dealing with visitors. They are truly welcoming — which is one of the reasons we can’t wait to return.

El Castillo, Rio San Juan

 The Fortress of Immaculate Conception: El Castillo, Río San Juan, Nicaragua


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