All Aboard with a Novice Cruiser: Panama to Costa Rica

A cruise novice discovers the joys of the seafaring life on a trip to Central America.

Authored by Andrew Weaver

Photo courtesy of Windstar

For most of my life, I assumed that I would go to my grave without setting foot on a cruise ship. To be clear, I harbored no judgement against them, or against the legions of good, honest people who enjoy them. It’s just that the idea of spending a vacation in the confines of a floating beach resort had never seized me the way it seems powerfully, almost religiously, to seize some people. Growing up, I had a friend whose family spent every school holiday cruising, and he always returned from his seagoing spring breaks with horror stories of intense motion sickness and interminable boredom. There are people in this world who cruise, I gathered from his cautionary tales, and people who do not. For twenty-eight years, I lived comfortably in the latter camp.

Of course, men “doth suffer sea changes.” Life takes unexpected turns. This past December, when I found myself hiking a steep metal gangway onto the Star Pride, a 212-passenger cruise ship docked in Colón, Panama, I wondered if, after decades, it was possible to switch allegiances after all—to become a person who cruised. A seven-night voyage sprawled before me. I was headed south through the Panama Canal with a company called Windstar, from the warm Caribbean to the Pacific Ocean and up the western coast of Panama into the lush lower reaches of Costa Rica. I had one small suitcase with a pair of sandals and a few shirts stuffed inside. I was also—unusual for a cruise ship—conspicuously alone.

“Just you?”

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This question, my first introduction to the ship, came from a smiling porter at the little desk where I had to surrender my passport to collect the key for my cabin.

“Yes,” I said. “All alone.”

“Windstar is perfect for the independent traveler,” he assured me, as though reciting from the brochure. “You’ll enjoy a solo trip here.”

Windstar, officially called Windstar Cruises, is known all over the world for its cozy, intimate boats and high crew-to-passenger ratio. It’s the small but mighty adversary to operations like Carnival or Royal Caribbean with their 4,000-passenger behemoths, some of which can span portions of the Grand Canyon. On a Windstar vessel, there are no casinos or clubs, no three-story water slides or miniature golf courses thronged with children. The Star Pride was not much longer than a football field. And that, I soon learned, was why everyone—every single person on board—had paid to be there.

After I’d checked in, a different porter led me up to the highest sleeping deck, to a forward cabin that was large and comfortable with a couch, a queen bed, and a balcony jutting out from the white parapet of the ship’s starboard side.

“Just you?” he said. Again, I explained.

The fact of my aloneness seemed to energize and excite him. A solo traveler, he told me, had the most to gain from a journey like this.

“It’s about the people,” he said. “They make the experience. You must meet everyone.”

I asked how many of us had boarded the boat, other than me, and he answered without hesitation: 155. This was something I would come to learn about Windstar staff over the course of the week. They’re armed with an unassailably perfect knowledge of the boat, the current voyage, and every passenger onboard.

I shook his hand. “One down, then.”

“One hundred fifty-four to go,” he said.

Photo courtesy of Windstar

The days run together on a Windstar cruise like a pleasant, sunny hallucination. The first part of the trip was marked mainly by eating and drinking and doing whatever I pleased, on my schedule. We spent the first full day traversing the Panama Canal—an experience Windstar augmented with copious onboard educational programming, including documentary screenings, Q&As, and live commentary megaphoned onto the main deck as we passed through the locks.

Taking the advice of the porter, I started to mingle with my fellow passengers. This happened mostly at the Star Bar, the open-air top deck outfitted with a hot tub and a stage for live music. Folks cruising on a small boat like the Star Pride, I found, are skeptical of privacy. What everyone wanted, the first few days, was to open up and break the ice.

“We cruise with Windstar,” a peppy woman from Queens named Maggie told me, “because we want to talk to people. Everyone does.”

I got particularly close with one family, a Floridian couple traveling with their two adult daughters, Kelsey and Quinn, and Quinn’s husband, Joe. I had dinner with them several times in the ship’s cozy restaurants, eating filet mignon and lobster the way one does on a cruise: for free. They had watched me from afar when I boarded the boat alone, they confessed, and wondered what I was doing there.

“We thought you’d been left at the altar,” Kelsey told me.

They were glad to find me just another cheerful vacationer. Kelsey, Quinn, Joe, and I were the only 20-somethings on the boat, and we got into a habit of staying up past everyone else’s bedtime, sipping whiskey on the dark top deck and watching the Panamanian moon light the way up the coast.

“If I had been left at the altar, this is exactly where I’d want to be,” I told them one evening.

“To life goals,” Kelsey said. We raised our glasses.

These new friends of mine had jobs and lives back on dry land somewhere, but we didn’t talk about that much. We talked about Panama, about the boat and the people on it. We speculated what kind of muffins would be served at breakfast the next day. If the basic purpose of being on vacation is to shuffle off more serious concerns and focus on things like muffins for a while, a Windstar cruise is the perfect place to do it. I found myself looser, calmer, and more amused with each passing day.


The second half of the trip was much more active than the first. After a few days of napping on deck chairs, gorging finger sandwiches by the half-dozen, and stopping in for massages at the spa, I was ready for some movement.

On the fourth day, we anchored for a beach barbecue at Isla Parida, an island off the western edge of Panama, where we swam and paddleboarded and hiked the forested trails of the island, working up an appetite for a feast of fish, lamb, and lobster prepared over open coals on the sand. The ship’s crew hauled a big floating trampoline out to the island and anchored it close to shore. We drank coconut juice and played in the sun.

By this point, I had met probably three-quarters of everyone on the boat, but I’d settled into a companionable rhythm with Kelsey, Quinn, and Joe, and spent most of my time hanging out with them. We bumped into each other at breakfast most mornings and took the tender to shore, exploring the Costa Rican ports that made up the latter half of the trip’s itinerary: Puerto Jiménez, Quepos, Puerto Caldera.

We went ziplining in the jungle, ate fresh fish at tiny open-air restaurants, and water skied when the ship was anchored in harbor. The slate of nightly activities on the boat filled with celebratory social happenings: salsa dancing lessons, trivia, cocktail hours. The crew put on a raucous talent show and dinners lasted late into the evening. As the end of the trip approached, people stayed up later, trying to wring the most from each day.

“Our parents are already talking about our next cruise,” Quinn said on the last night, after a farewell meal that featured a speech from the captain, who thanked us all for coming. “We are now, officially, a Windstar family.”

We all agreed: There are worse things to be.

Photo courtesy of Windstar

The disembarkation process was quick and painless. There wasn’t enough time to say goodbye to everybody, which was for the best. Watching everyone leave the boat, I tried to spot someone I hadn’t met, but couldn’t. It seemed I had reached my goal.

A shuttle whisked us off to San José, Costa Rica’s nearby capital. From there, some of our cohort ventured deeper into the country to extend their stay, but most went grudgingly to the airport. Sitting in the terminal, waiting for the flight that would carry me home, I opened the Windstar webpage on my phone and started looking through upcoming voyages, scanning the itineraries and ports—something only a cruise guy would do. I had been converted, after all.

As we lifted off and I watched Costa Rica fade beneath the clouds, I pondered what this meant. Of course, it goes without saying that no one (except the odd journalist) steps onto a cruise ship agnostic about cruising. Everyone has paid good money to be there. But a true cruiser’s dedication goes beyond the normal excitement of a vacationer or a paying customer. The cruise is a tribal, all-consuming way to travel, and that, in the end, is what makes them so great. The physical confinement of the ship and the relentless enthusiasm of the programming obliterate all thoughts of responsibility, reality, dry land. The relaxation is sedative. The friendships made, while short-lived, have the delightful intensity of summer camp attachments, of pals who come from elsewhere, stick by your side for a while in the sun, and then head off, back to faraway lives of their own.

Photo courtesy of Windstar