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Hitch-Sailing: A Ticket to Cruising Paradise?

DATE POSTED:March 5, 2025
Aerial view of island in the Kingdom of Tonga The many paradisiacal islands awaiting in the Kingdom of Tonga are a cruiser’s delight. Simon/stock.adobe.com

We sailed into the Kingdom of Tonga at dawn after five days at sea. The verdant shores looked like broccoli tops through the wet haze. Huddled under my rain jacket, I stood at the helm of Compass Rosey, a 43-foot Polaris older than me, with my Nescafé. I breathed a sigh of relief when the hills blocked the ocean swells. During my watch, our speed had dropped to 3 knots in the light air, making the broadside rollers particularly nauseating as we pitchpoled between them.

During the past six months, my husband, Rob, and I had bobbed for 33 days from Panama to the Marquesas, and crewed on several multiday jaunts between anchorages in French Polynesia and the Cook Islands. You’d think that after crossing 4,500 miles of the world’s largest ocean, I would be a seasoned bluewater salt, right? Immune to rollicky seas, with legs of steel? Happily singing chanteys while munching on canned veggies and soggy crackers? 

Rob with sailboat in background The author and her husband, Rob, had dreamed of buying their own boat to sail the South Pacific. Hitch-sailing allowed the couple to sample the great life afloat on a budget before fully diving in. Courtesy Brianna Randall

Nope. This passage had been just as uncomfortable and monotonous as the last several.

Sipping my tepid coffee, I reminded myself why I’d upended my life at age 33 to hitch rides across the Pacific. To see the infinite blues of the sea and sky. To marvel at the fact that two hunks of canvas can cart us across hundreds of miles. To embrace the solitude of gliding alone across watery wilderness. To take pride in managing my mind, body and boat at sea. And the cherry on top, the real reason I’d signed up for all these ocean crossings: to visit crystal-clear lagoons and postcard-perfect islands.

The trade-off was having to pass by anchorages we desperately ­wanted to explore, yield to questionable ­decisions, and rely on others’ ­navigation skills.

We’d made it to the reward again. As the water under our keel turned from cerulean to jade, the boredom and discomfort from the passage evaporated. 

I steered us toward the biggest horseshoe-shaped island in the clump of 30-odd specks that comprise Vava’u, one of four island groups in Tonga. In the center of the horseshoe sat Neiafu, the second-largest town in the kingdom, with 3,900 people. All told, Tonga’s islands take up nearly as much ocean real estate as the Caribbean islands but have a tiny fraction of the Caribbean’s humans. I grinned, excited to explore the deserted beaches and miles of teeming reefs.

I set our autopilot and roused the rest of the crew. Our captain, Mark, called the customs office on the VHF radio to announce our arrival, and then perused the charts for moorings. Rob groaned as he hefted himself into the cockpit, draping himself on the bench beside me. He suffered from seasickness, so the slow rocking last night hadn’t done him any favors. 

“Smell that?” I asked as I gulped in an exaggerated breath. The pungent scent of flowers and fruit was striking after days offshore, both pleasing and overwhelming. “Dirt, baby.”

“Mangoes, here we come!” Rob said with a fist pump. It had been a month since we’d been anywhere with enough soil to grow food. 

Compass Rosey was the fifth boat we’d crewed aboard since leaving our home in Montana. Originally, as we plotted our midlife escape from landlocked 9-to-5 jobs, Rob and I had dreamed of buying our own boat to sail the South Pacific. We’d created budgets and voyaging itineraries, researched trade winds and provisioning ideas, and saved as much money as we could. 

One year into planning and scrimping, we realized that it would take many more years to make our dream a ­reality
—unless we used someone else’s boat. We altered course and decided to crew instead. Cruisers often look for an extra pair of hands to help with watches and chores during long passages.

We posted on Cruisers Forum, advertising our services in exchange for a lift to French Polynesia. A family of five from New England answered our ad. We spent two months aboard their 53-foot steel ketch, transiting the Panama Canal from Colón and then sailing downwind to Nuku Hiva in the Marquesas via the Galápagos. That 33-day Pacific puddle jump included endless games of Scrabble, a visit from a lone orca, and a lot of jumping jacks on the stern.

parade in Vava’u Amid the rhythmic drumming of a traditional parade in Vava’u, Tonga, the couple savors a rare cultural celebration. Courtesy Brianna Randall

After our first prearranged ride, we relied on hitchhiking to hop between islands. Or hitch-sailing, as I dubbed it. Many cruisers follow the same route on the “coconut milk run,” leaving around March from the Americas and traveling the trade winds east to west to make it to New Zealand or Australia before cyclone season starts in December. That means we saw the same two dozen boats at most anchorages. Though pickings were slim for hitching a ride, it also meant that we became friends with the people on these boats, and they were more inclined to give us a lift. 

Our second ride from the Marquesas to the Tuamotus was a C&C 40 with a young couple. Third, we hopped on a Choate 40 with a retired couple to get to Tahiti. Fourth was a short ride with a British singlehander to Huahine in French Polynesia. Then we joined Mark, who was delivering Compass Rosey to Australia for the boat’s owner. 

I like to think that Rob and I are easygoing folks. But even the most flexible adults would start to feel weary after adapting to five different captains who each had a set way of doing things—and varying degrees of openness to suggestions. We’d learned a ton about bluewater sailing and saved hundreds of thousands of dollars by volunteering as crew. The trade-off was having to pass by anchorages we desperately wanted to explore (we’ll be back for you, Maupiti), yield to questionable decisions (like sailing with no running lights one night off Tahiti’s busy shipping channel), and rely on unfamiliar equipment, and others’ navigation skills (which once plowed us into a reef while sailing at 7 knots).

Snorkeling with sharks Swimming alongside reef sharks in crystal-clear Pacific waters led to thrilling moments that made their sea hitchhiking adventures even more unforgettable. Courtesy Brianna Randall

Rob and I were ready to be the masters of our own destiny. We were jumping ship in Tonga and had planned to stay ashore for a bit. We’d hoped to rustle up a boat-sitting option during the upcoming cyclone season.

As Neiafu’s deep, protected harbor came into view, I took in our new digs. Shiny yachts mingled with dilapidated wooden skiffs. Onshore, crumbling concrete ruins slumped next to brightly painted houses. On one hill, a white church sat picturesquely, its bells ringing. A taller hill, crowned with a radio tower, rose behind the bay, with a path winding up the side. I couldn’t wait to climb to the top to stretch my atrophied legs.

We pulled up to the customs dock, and Rob greeted the official who ambled toward our boat: “Malo e lelei.

He always made sure he knew how to say “hello” and “thank you” in the local language before we arrived. Along with a smile, those two phrases worked like magic in most countries.

Bri cutting into a cheesecake Along the way, the couple learned to embrace life at sea. Courtesy Brianna Randall

In our cruising guide, I’d read that Tongans use three languages in their kingdom: one for royalty, one for nobility, and one for everyone else. Luckily, we’d be able to get by with English because most Tongans are fluent in that as well. After our passports were officially stamped and we’d picked up a mooring ball, Mark dinghied us to shore with our belongings: a few backpacks and one beat-up guitar. We bid him farewell, then turned to walk the six blocks of Neiafu’s main street. Kids in navy-blue-and-white uniforms walked to school. The market was coming to life, with mounds of spinach, pineapples, eggplants and tomatoes as music to my eyes. The largest building downtown, made of whitewashed brick, housed a souvenir shop, a beauty parlor and an open-air Italian restaurant. A shop called the Tropicana promised ice, laundry services, and pay-by-hour computers. The grocery store had mint-green walls and sold either vanilla or strawberry ice cream by the scoop from a wrought-iron window. Chocolate came by boat once a week, we learned, and sold out fast. An ATM on the corner shelled out pa’angas, valued at 2 to every 1 US dollar. Chickens cock-a-doodle-dooed in rising crescendos, and pigs roamed the streets. Yes, pigs. Big fat ones, little baby ones, pink-and-gray and speckled ones. They grunted in the gutter, scarfed down garbage, and scuttled through the foliage in search of rotting fruit.

We headed back to the Italian restaurant for espresso with real cream (a treat I hadn’t had in months) and asked the lovely Tongan waitress about the roving pigs. “We roast them to celebrate birthdays, weddings, funerals,” she told us, setting down my fruit smoothie and coffee. “The more pigs you have at your funeral, the more important you are.” 

Rob toasted me with his cappuccino after she left. “I think Tonga will fit us just fine.” After our snack, we found a room. It had a shared balcony overlooking the harbor, a bed with a significant sway in the middle, a tiny bedside table, and one electrical outlet. 

Brie exercising Figuring out how to stay fit by working out on deck in the middle of the ocean. Courtesy Brianna Randall

It was 10 times bigger than any of the berths we’d occupied during the past six months. It didn’t move. No one would wake us at midnight for watch. Supposedly the internet worked too. A dream come true. 

Brianna Randall hitch-sailed aboard seven sailboats with her husband, Rob, in 2013. They visited 25 tropical islands in nine countries and learned that they really like being the captains of their own destiny.

Hitch-Sail  (´hĭch-sāl)

1. Soliciting free rides at marinas, anchorages or ports where sailboats congregate.

2. Working as volunteer crew on a private yacht in exchange for passage across the sea. 

Sailing off into the sunset is a common dream. Actually buying a sailboat and navigating it to foreign shores is less common. One compromise for those antsy to get a move on—or for those looking to gain bluewater experience—is to hitch a ride on someone else’s boat. With a bit of forethought and a healthy dose of patience, you can get a lift to your desired destination. Here are a few tips:

  • Get to know the captain, virtually or in person, before you commit.
  • Negotiate up-front ­whether you’re sharing food and mooring expenses.
  • Chip in early and often with chores such as night watch, cooking and cleaning.
  • Pack light; one waterproof backpack should suffice.
  • Bring your own ­seasickness meds.
  • Be resilient, ­adaptable, and at peace with uncertainty.

—BR

The post Hitch-Sailing: A Ticket to Cruising Paradise? appeared first on Cruising World.