Considerably beyond the halfway point of the South Pacific Milk Run, there is an island group where yachties sail “inside” in smooth, protected water. Where the king banned all whaling in 1979. Where pigs run free, and people don’t dress, or think, like you and me. Where a regatta in its infancy could become the biggest local festival going. But I offer fair warning: some cruisers make it to Vava’u, the northernmost island group of the Kingdom of Tonga, and never leave.

Once upon a time, Ben and Lisa Newton sailed their pilothouse sloop around lovely San Francisco Bay. The sea breeze was brisk and fine, but, let’s be frank, it was cold. In 2002 they set out to sea to see, well, whatever there was to see, and three years later found themselves in Vava’u. The tradewinds were mild and fine—and very, very warm. Lisa explains: “We spent a cyclone season here in Vava’u, in one of the best-protected storm holes in the South Pacific, and we fell in love with this island group and the local people. Imagine sailing in consistent tradewinds on lagoon-like waters with stunning geology, lots of anchorages, friendly people, whale sightings every day during the season, all in a central location in the South Pacific. We were lacking a regatta here, so in 2009 we created one.”

And that, friends, sums up the pitch that lured a sailing journo on a very long plane ride to Vava’u, which I found is as advertised by the Newtons, who arrived there aboard a boat called, appropriately, Waking Dream. The local government has no plan to disrupt the happy subsistence-agriculture economy by selling out to big tourism, so for the imaginable future, those who wander can wander here and find it unchanged. Which is to say that, unlike the lagoon at Bora Bora, Tahiti, there are no jet skis.

Wanderers passing through Vava’u this year included two boats from Seattle, Washington, that sailed in company all the way from the American mainland. That would be Piko, a Wauquiez 35, and Dilligaf, a Jeanneau 49DS. Their crews first became aware of each other when outbound on the Baja Ha-Ha Rally from San Francisco to Cabo San Lucas.

“We had to go all the way to Mexico to meet our own neighbors,” says Dilligaf skipper Bill Teasdale. “Going down Baja we kept tabs on Piko. We knew about Lauren and Lauren, but we didn’t meet them until the Puddle Jump Seminars in La Cruz. We shared dinners and drinks and sailing stories. Then we talked over our Pacific-crossing plans, made a new plan, and left La Cruz within hours of each other. We stayed in contact through the Puddle Jump Net, and we made Nuku Hiva within a day of each other.”

Add time spent exploring the Marquesas together, and the friendship grew in a way that speaks volumes to what people really do once they’re “out there.” Sure, there are some hermits, but cruisers by and large are a gregarious lot. They enjoy meeting the locals, but they also form natural bonds with people who have made the same sort of do-it-now decisions. Choosing a next destination, fixing what broke on the last leg, picking a departure time, crossing an expanse of ocean with or without heart-thumping adventures, viewing the rise of the next landfall—these experiences keep a person vividly alive in the moment. This is what it’s all about. Sharing that in Mexico in the ports of La Paz or La Cruz, or again in the Marquesas, Tahiti and Tonga and onwards—that’s powerful medicine.

Imagine Teasdale or his wife, Sue, many sail changes and position fixes down the line from Mexico, looking out across a Pacific anchorage and saying, “Look, there’s Piko!” There would be so much to talk about. And it would be much easier than trying to parse it all out for folks back home, locked into their routines, freeway-glazed or worse. The islands of the South Pacific may have been “discovered” long ago by people with names you read in history books, but every voyage is an eye-opening, personal discovery. Every voyage stands alone.

At one gathering, surrounded by wanderers, I hit Teasdale with a thought of mine—that many people setting out imagine cruising as a month of Sundays when, in fact, boats are taskmasters, and voyaging under sail makes for a month of hard-puttering Sundays. His answer? “Better than a month of Mondays.”

Ex-Navy. Ex-dive pro. I reckon he knows.

Hard puttering was on my mind, because I was reading Larry Jacobson’s book, The Boy Behind the Gate. Jacobson is a circumnavigator who discovered, one hard lesson at a time, that cruising is the art of fixing your boat in exotic places, brand new equipment and gear included. And still he loved it. His message is, you probably have a lot of things that hold you back from taking a long cruise. They are good things, meaningful things: friends, home, possessions. “But don’t let the good get in the way of the great.”

Out there, you will find no lack of memorable company, and every now and again it’s right to rally-up with a bunch of like-minded folks for a bout of friendship-deepening silly fun. Enter the Regatta Vava’u and Festival.

First you have to arrive. Let’s peek into the log of Mr. Lauren Buchholz as Piko approached landfall, remembering that, strangely enough, boats seem to arrive in the dark about half the time. The Mrs., also named Lauren, was asleep below. (Even before they got to Mexico, inevitably, they were famed in the Pacific fleet as “Lauren and Lauren.”) Buchholz wrote, “Last night I pulled a double watch. Then again, we crossed the international dateline, so did I really? At least it makes our check-in easier. Before we crossed that magical line, it was Saturday. Now it’s Sunday, which means that when we arrive tomorrow it will be Monday morning, and we won’t have to wait for Customs, except—right now it’s blowing 20 knots and we’re dead downwind. This puts us into Tonga in the dark, which isn’t good. We already have both reefs in the main, with no headsail. We have to slow down even more, and I’m still working on this whole slow-the-boat thing. I’m thinking we’ll sail around the north end of the island to get out of the swell and then heave-to until the sun comes up.”

And then, there they were. In a very-other place. One word from the Tongan language has entered English. Tapu, or taboo, in Tongan can mean either forbidden or sacred. In the airports, smoking is tapu. The fundamentals of Tongan culture have made it pretty much intact to the 21st century, so you won’t find Tongans eating in the few restaurants that cater to tourists and resident “palangis,” their word for un-Tongans. Their way is still the big cookpot for the big family and the big cast of who-knows-how-many more who might show up, and that is just fine. Their way is ceremonial. Society is a complicated hierarchy that makes perfect sense, to Tongans. If I were qualified to explain, I would. But I get it that pigs run free, and people here build fences to keep pigs out, not in. And I get it that the long wraparound skirt called a tupenu, topped by a woven waist-wrap, a ta-ovala, is an appropriate schoolboy uniform for either a festive or solemn occasion.

Regatta Vava’u is one thing, with its own reasons for existing. Its companion piece, Festival Vava’u, is another, meant to bring the town of Neiafu and the entire island together. I saw it happen. I was a witness.

The Chanel High School Band kicked things off, lighting up a food and crafts fair that shut down “Main Street” for the Wednesday opener and, in turn, shut down in time for the Zillion Dollar Pub Crawl. (Palangis only for the pub crawl, of course.) Thursday morning was then dedicated to an information session regarding New Zealand, for the many headed that way at the onset of the South Pacific cyclone season. After that, it was on to the Tridecagon-Athlon, a session of games and hijinks. Rope pull. Egg toss. Four-legged race. Much more.

My strongest memories of Vava’u are of the sailing and of Kid’s Day, which dawned clear and bright. Kid’s Day is exactly how it sounds: face painting and games for the local kids, orchestrated by hardworking, hard-playing volunteers led by Jason and Billy. The brief on Billy is that he grew up in a circus, and he’s worked every job in a circus. I watched him train new stilt-walkers and stilt-walk tutors (“always one foot in front of the other; always one hand ahead; eyes up, eyes up”) and then lead one game after another until it was time to lead a parade. Down “Main Street” they came, scores of kids, little to almost big and—Tongans being musical by nature—cheerfully and in perfect cadence chanting,” Regatta, Regatta, Rega-ta-ta, Regatta, Regatta, Rega-ta-ta!” What followed was a performance of traditional dances by kids from three of the island’s schools. Yachties were welcome to watch, but having seen my share of floor shows in Waikiki, I can assure you this purely a local thing, neither for or about us.

The audience sang along with the performers, one age group after another, with women coming around giving money to show approval. And then, at last, it was time to race. I sailed two of three races aboard the 50-foot sloop Relapse, built by owner Mark Edwards to a 20-year-old Jim Young design, but looking fully modern. Even if we didn’t win the water-balloon/squirt-gun wars, we at least finished first in section in both races. (Water balloons in the pre-start? Why not?)

Figure that 81 boats were involved, with 20-something joining this race or that, and let’s check the competitive temperature by first studying Chog’s Rule, and then the finish of Relapse in Race 2. Chog’s Rule applies to the weekly Friday night race at Nei’afu, where the late Chog always ran last. For Chog’s sake, a rule was implemented allowing the last-place boat, when the next-to-last boat rounds the final mark, to turn for the finish. Chog’s Rule endures, with the Friday night race folded into Regatta Vava’u. Fortunately, we aboard Relapse did not need Chog’s Rule to cover ourselves with glory.

In the second race, the rains returned, and while a nice breeze came with the rain, in the mist that followed, not so much. Still, Relapse is a performer, and we finished in the light stuff, ghosting along with Mark and his wife, Catherine, watching as their boys, Ash and Cameron, did repeated cannonballs from the end of the boom. We figured that fit perfectly the racing rules definition of finishing by crossing the line with any part of hull or crew in normal position.

The next day I hopped aboard an ex-Moorings 40, under delivery to New Zealand, for the final race (The Moorings has a charter base in Neiafu, so you could take part in the regatta without having to sail there aboard your own boat). By then we had also experienced the Full Moon Party—Burning Man comes to Tonga—and now it was sunshine, not rain, flooding down. We didn’t exactly win race three, but we could still see the leaders at the finish. And so, to the point:

Roughly 20 percent of boats sailing through the South Pacific in any given year include Tonga in their itinerary. Regatta Vava’u and Festival was created to augment that number. Not dramatically—Tonga is not prepared to handle a major influx of anything—but an incremental increase, yes. Checking in once again with Buchholz: “We were always planning to pass through Tonga,” he said, “but the regatta gave us a date. We were pleasantly surprised. For a start-up, the organization was impressive, easily on par with the Banderas Bay Regatta and the Puddle Jump Rendezvous. We intend to plug it with our friends and, depending on where we are, we might even come back next year.”

Fair enough. We all lived more than 5 days worth in 5 days time—on island time. Nothing wrong with doing that more than once.