From our back porch in Annapolis, Maryland,we gaze out on 6 miles of the Chesapeake Bay at the mouth of the Severn River. On a good summer weekend, we’ll see scores of sailboats milling about—hundreds if a big regatta is on. Some will catch the eye and get you to take a longer look. But only one stops me in my tracks every time.

Well, two, actually: the schooners Woodwind I and II. They are swan-white 74-foot twins that carry tourists on two-hour cruises daily from early spring to late fall. They’re just too pretty to ignore.

So it is with schooners. There’s something about the beamy, swooping hull shape and the dynamic angle of the rig that demands special notice. With a short mast forward and the tall one aft, the sail plan looks like a butcher’s knife cleaving the wind. When all the canvas is up and pulling—two or three jibs, foresail, topsails, and main—these graceful boats carry an air of timeless utility and majesty. 

Imagine the scene 150 years ago, when schooners by the hundreds roamed the coast, laden with cargos of lumber, coal and other dry goods. What a sight to see them tacking and jibing off Cape Hatteras, North Carolina, or Provincetown, Massachusetts, killing time waiting for a fair breeze to make the rounding.

No boat is perfect, of course, and schooners have their ­downside. Fred Hecklinger, the late guru of wooden boats around the Chesapeake, used to say, “If you love schooners, get a picture of one and put it on your wall.” It was his way of ­acknowledging that for all their beauty, schooners of old were also heavy, not particularly good at going to windward, and relatively slow except on a screaming reach.

There’s only one place left on the East Coast where you can reliably see a gaggle of schooners hard at work on any summer day, and that’s Penobscot Bay off midcoast Maine. A dozen or so of the wooden beauties up to 100 feet long charter, offering four- to six-day trips out of Rockland and Camden. Smaller ones run daily excursions. A few are purpose-made for the charter trade, but most are meticulously maintained relics of the ­freight-­carrying past, including two—Lewis R. French and Stephen Taber—that each turned 150 years old in 2021.

Schooners hold a special place in my heart because they’re where I caught the sailing bug. Sixty years ago, my father and I took a four-day trip on Mattie out of Camden, Maine. It was the first overnight sailing trip for either of us. We drove up from Long Island, New York, stopping at Cape Neddick, Maine, where I cracked my first lobster claw. We boarded that night for early departure next morning. I was 16.

Mattie’s new owner and captain was a slim fellow named Jim Nesbit, who showed us around what would be our humble digs for the next few days. Mattie was then 78 years old, having launched in 1883 in Patchogue, New York, just 37 miles from our Long Island home.

The old freighter had few amenities. Lights were kerosene, and cabins were tiny and had no portholes. The head was dark and airless. Meals, including daily fresh bread, were cooked on a cast-iron wood stove. Passengers ate on deck or in a dim, low-slung main cabin. Back then, there were no electronic navigation aids, so when fog swept in, you made your way to the next anchorage by guess and by God, with a man in the bow sounding the mournful foghorn while peering through the mist for danger.

We found our fog the third day out, thick as soup. I was a nervous rabbit, so when we finally heard the clang of a bell and then saw a green buoy heave up through the mist as proof that we were safe, the moment of relief and joy formed my lasting attachment to sailing and the sea.

Advance the log by 60 years, to 2021, and little has changed. We’re back in the same cold, clear waters off Vinalhaven, Maine—the biggest island in Penobscot Bay—and the fog is back, thick as ever but no longer quite so scary. We know where we are thanks to electronics. The chart plotter inside a varnished box near the helm shows precisely where we’re going.   

Everything else remains much the same. A starry, moonless sky at midnight. The gauzy curtain that hangs as dawn gives way to misty day. A protected cove at daybreak with no breeze, ripples emanating from a circle of bait as little fish spin nervously on the surface and seals lurk below, popping up to grab a snack. Eagles and ospreys wheeling overhead; terns squawking and dipping for minnows; black guillemots, a northern seabird, paddling along the bank.

 A dark blockade of spruce lines the shore, ending in a band of pale granite, beneath which sweet-smelling seaweed clings from the high-tide line down to the ocean, which will rise and fall 10 feet and more with the diurnal pull of the moon.

Then there’s our boat itself, pretty as a picture once the sails are up and pulling. 

When my wife, Fran, and I decided to take a trip back in time this past summer, the schooner we chose was Heritage, out of Rockland, Maine. It’s one of the bigger vessels in the modern fleet at 95 feet on deck, and one of the newest, launched in 1983. It’s the creation of Capt. Doug and Linda Lee, who built the boat over three years in the boatyard they own at the foot of Front Street.

If the Lees took advantage of modern technology in construction, you couldn’t tell by looking. Heritage weighs 165 tons. The frames and hull are oak, steamed and bent to shape. The decks and cabin tops are straight-grain pine. Heritage has no engine for propulsion; to get in and out of tight spots, this vessel (like most in the fleet) uses a diesel-powered push boat that tucks quietly under the stern.

The Lees did have the advantage of designing Heritage for people, not freight, so they could fashion a central cabin for dining where everyone can sit at once, instead of in shifts. Other than that, this is a traditional Maine schooner, stem to stern. Meals are prepared on the antique wood stove, and sails are heavy canvas. To raise the weighty gaffs, sails and anchor, the crew fires up Old Joe: a 1921, make-or-break, single-cylinder donkey engine that the Lees rebuilt from junk. It snorts like a misfiring freight train.

Twenty-nine of us, a full house, paid to board this sturdy anachronism to stuff ourselves into cramped cabins, to clamber up the companionways in the dark to use the head, and to wait our turns for the only bathing facility: a showerhead on the end of a flexible tube in one of the three heads.

Missing, sadly, were the Lees, who sailed Heritage for 37 years after they built it. Now in their 70s, they sold the schooner to two crewmen in 2020, when chartering was suspended in the pandemic. 

Fortunately for the new owners, 2021 proved a boom year, as vacationers looked for holidays closer to home. I don’t remember it, but Fran says that I came home the day in March when I got my second vaccination shot and announced that we were going schooner sailing in Maine.

You might wonder why a couple with their own cruise-worthy sailboat (albeit small, at 27 feet) would drive 11 hours to get on somebody else’s boat with a crowd of strangers. The answer is uncomplicated: The food is plentiful and good; the scenery is incomparable; the company is generally soft-spoken; and it’s nice to find yourself in the hands of competent, cheerful young people whose main interest is keeping you safe and happy. You know, instead being the one who is fretting about rocks and tides and fog.

The new co-skippers of Heritage are a pair of bearded, scruffy, 30-something bachelors who worked for years on the vessel, and who seem as devoted to tradition as the Lees were. 

Capt. Ben Welzenbach was teaching guitar in Chicago nearly a decade ago when his dad took him on a father-son trip on Heritage. As soon as he got home, Welzenbach sent a job inquiry. He was on the deck crew the next season. 

Capt. Sean Grimes was a line cook in a southern New Hampshire restaurant when a buddy dragged him to Maine and introduced him to schooners. The next year, he ran the wood stove on Heritage.

Welzenbach had the helm and Grimes was in the push boat when we departed Rockland under a mackerel sky and little breeze. Passengers ranged in age from 15-year-old Cassidey Card of Connecticut, tagging along with her grandparents, to 85-year-old Faith Hadala of Tennessee, who quizzed anyone who looked like they might be in the running to make sure she was indeed the oldest.

Hadala was with her 84-year-old husband, Paul. Her first marriage lasted 17 years, she said. The second also lasted 17. She and Paul had been together 16 years. “We’re waiting to see what happens next year,” she said with a chuckle.

Schooner trips skew to the upper age brackets. You won’t find many go-go, 40-something J/70 racers from Scarsdale, New York, on the passenger list. They’re more likely down in St. Martin sipping Red Bull and vodka on a Caribbean beach.

But you still do get characters, like Bo Kinsman, a lobsterman from Ogunquit, Maine, who takes a week off every month in summer to sail on Heritage. He likes going from having to do everything on his boat to doing nothing on the schooner. A ringer for Ernest Hemingway with his silver fringe beard, gimlet eyes and battered fishing cap, he usually works alone tending 400 pots on a 32-footer.

He surprised us when we stopped the first night at tiny Burnt Island for our lobster bake, a staple of every Maine Windjammer cruise. We had 65 live lobsters in a tank; the crew steamed them over a wood fire in a blanket of seaweed plucked from the rocks. They were unbelievably fresh, and you could eat all you wanted. Kinsman took none. He chose hot dogs and burgers. “I don’t eat lobsters,” the lobsterman sniffed.

There were other bright lights in our thrown-together crew. Steve Berthiaume, who builds flutes in Massachusetts for a living, brought a travel guitar and led singalongs at night while his wife, Kim, sang nice harmonies. Suzanne Farace, a divorce lawyer from Baltimore, spun yarns about previous kayak-camping trips she’d made in Penobscot Bay. Her paddling partner, John Garon, told of his days as a spy in the National Security Agency—no state secrets but good palaver nonetheless. Jill McConnell of upstate New York jumped in and swam around the boat for an hour one evening, as if we were in the Bahamas, which we certainly were not.

The crew were young, with interesting lives. Ginger-haired Courtney King was born to the sea: Her parents own the schooner Mary Day out of Camden, and she’s working on her own master’s ticket at Maine Maritime Academy. She hopes to buy a small schooner to live on. Kyle Gray was working long hours at a commercial real estate firm in New York when he decided to kick over the traces and work long hours climbing the mast on Heritage instead. He’d be heading to the University of Pennsylvania to study education policy in the fall.

Our cook, Stephanie Cech, was a wiry small-boat racer in Ohio when she got the urge to head east. Everything she knew about cooking meals for 35 people on a wood stove she learned in a few weeks from Capt. Sean, who rose at 5 every morning to help her start the fire. It was fun watching her pound out huge blobs of dough for the daily bread. 

Jeremy Schmich was bored writing software code for a living. Now, he’s in charge of Old Joe, the donkey engine, and arms himself with an oil can and ether spritzer to get it going. “First time, every time,” he chanted while spinning the flywheel with one hand and tickling the compression release with the other, hoping for the chug-chug-BAM that signaled success.

We never got much wind. Usually in Maine you can count on an afternoon southwesterly sea breeze, but this year was fickle, Capt. Ben said. Yet, the push boat was quiet enough that you barely knew it was running, and the sails were up all day to catch any breeze that came along. The scenery never disappointed. At 68 degrees, the water was warm enough for the bold to swim. And three lovely old rowboats were launched at each anchorage for exploring the shore.

All in all, it was a memorable trip. Yes, you could occasionally hear the guy in the next cabin snoring, and the shower situation took some getting used to. But there is much to admire in a place that has changed little in 150 years.

The Maine charter trade for schooners was hatched in 1936 by a 20-year-old entrepreneur named Frank Swift, who saw the sailing fleet moldering away as motor vessels took over. He wondered if a boat could be cleaned up and pitched to adventurous vacationers as a cruise ship. He found a skipper and a boat, dubbed the enterprise Windjammer Cruises, and sold the first trip to a trio of ladies from Boston who paid $35 for a week on board.

Twenty-five years later, when I got my sea legs on Mattie, an industry was already in place. It’s still thriving today. I asked Courtney King if Mattie was still around. “Oh, sure,” she said. “She’s out here doing the same thing we are. She’s still running out of Camden. They changed her name, though, back to the original: Grace Bailey.”

She tugged on my sleeve the next day and gestured across the sparking sea to a sailing relic, shining proud and going strong at 138 years of age. “There she is,” she said. “There goes the old Mattie.”

Angus Phillips is a longtime Chesapeake Bay-based racing and ­cruising sailor, former outdoor columnist for TheWashington Post, and frequent contributor to CW.

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The thrum of the diesel engine reverberated through the teak deck and up through the soles of my heavy furry boots as Passing Cloud slipped smoothly through the almost-black waters of British Columbia’s Seaforth Channel. The Heiltsuk First Nation community of Bella Bella faded into the distance as we headed out on our adventure in the Great Bear Rainforest. Overhead, the skies were leaden, promising rain, much to the joy of the crew.

As a fair-weather sailor, the idea of a rainy week aboard the 71-foot classic wooden schooner sent chills up my spine. But I understood their joy and simply added another layer of clothing.

After all, when summer turns to fall, and wild Pacific salmon migrate toward their native rivers for spawning, “pray for rain” is the cry echoed all around the area. This year, the rivers were too low, causing major concern that the annual rains would be coming too late for the iconic fish.

Salmon are the lifeblood of the area’s First Nation people, who rely on the yearly migrations not just for food, but also as the symbols of abundance, fertility, prosperity and renewal. This all tied into Passing Cloud‘s overreaching commitment of connecting people with nature, fostering stewardship, and reducing their carbon footprint.

This was my second trip aboard Passing Cloud. A couple of years earlier, I was lucky enough to experience a voyage to Haida Gwaii—also known as the Queen Charlotte Islands—an experience I won’t ever forget. When this trip presented itself, I jumped at the opportunity to explore the Great Bear Rainforest in mainland British Columbia.

The Rainforest is a wild and dramatic region, one of the world’s largest, intact temperate forests that covers more than 24,000 square miles of land and sea. The spectacular scenery forms a backdrop for whales, dolphins, bears, wolves, sea lions, sea otters, and a vast variety of pelagic birds that depend on the health and viability of the wild Pacific salmon.

Hence the joyful prospect of rain after the dry summer.

Passing Cloud‘s crew included Russ Markel, skipper and owner of the boat and a marine biologist; Liam Ogle, the widely traveled and experienced first mate; Erin Vickars, our super-­talented Red Seal chef (the designation comes from a prestigious Canadian internship); and Briony Penn, our onboard expert with an encyclopedic knowledge of the flora, fauna and people of the area. And then the six guests, including me, who had flown in from around the world to experience this once-in-a-lifetime trip. They included a couple from South Africa, a single woman from England and a local couple from Vancouver.

It felt good and familiar to be back on board, and as I looked around, I noted the upgrades and other changes that had been made during the intervening couple of years. Most significantly, a set of new, flexible solar panels covered the top of the pilothouse, which significantly increased battery life. They also significantly decreased the boat’s carbon footprint, a major component of Passing Cloud‘s mission.

One of the unique aspects of these adventure trips is that although there is a basic timeframe and itinerary, the tides, weather and animal sightings rule. Insider knowledge and boat-to-boat communications play a huge part, with unexpected sightings and information constantly (and sometimes drastically) altering our route. But the location of whales and other animals one day can change by miles overnight, so there is never a guarantee that the animals will be sighted. The biggest challenge was to spot the elusive “White Spirit,” or Kermode bear, a rare subspecies of the black bear.

According to legends of the Gitga’at and Kitasoo Native ­peoples, Raven, the creator of the rainforest who made everything green, decided to make 1 in 10 black bears white, to remind him of the time when the world was white with snow and ice. Raven decided to set aside a special area of the world for these bears, which is now known as the Great Bear Rainforest.

The general itinerary was to go west, then turn north around Ivory Island, zigzagging up and around Princess Royal Island; proceed east and then south through the Fiordland Conservancy, ducking between Susan and Dowager islands; and then head a few miles north to Klemtu, an isolated fishing village. Then it would be south, and finally back east to end up where we started, in Bella Bella.

Before we were even underway, the steady flow of food began. Erin, our young chef, produced gourmet meals around the clock. From early-morning coffee to a late-evening dessert, the food kept coming. As a professionally trained chef, Erin didn’t simply prepare food—she presented beautifully plated meals.

A new feature of these trips aboard Passing Cloud is that each dinner is themed to express the experiences of that particular day. We had appetizers that depicted birds’ nests on the day we saw the sandhill cranes. And a chocolate-ganache dessert with tiny bear prints on the first day we saw bears. We even enjoyed unique woven cucumber strips topped with creme fraiche and salmon roe, the weaving representing the baskets used by the people indigenous to the area.

But more important, the choice of foods pointed to the sustainability aspect of the trip. As much as possible, food and supplies are sourced locally, which is a feat unto itself, given the remote location. During our eight days aboard, we saw only one other community, Klemtu, besides our departure port of Bella Bella. The menu included fresh local seafood and vegetables, supplemented with foraged greens from shore excursions. Several dinners were vegetarian, going along with sustainability, but Erin is very conscious of nutrition, and the meals were completely balanced. Two large ice chests and a freezer on deck, packed with supplies that were either flown in or brought in by boat, formed the basis of the menu. We were so well-fed that at one stage, I had to ask for smaller portions and declined the between-meal snacks.

As we wove our way up the channel on that first day, the only other vessels we saw were a couple of small commercial fishing boats. Cruising slowly, binoculars and cameras at the ready, we passed by the classic Ivory Island lighthouse, its fresh white walls and bright-red roof shining in the sun that peaked out from behind the lowering clouds.

And then…our first humpback whale sighting. Sharp eyes spied the spray shooting into the air, then the curve of an enormous back slipped above the water, followed by the iconic tail flap. Although they were a distance away, cameras snapped madly. Little did we know how plentiful these gentle giants are in the area and how many we would see.

The humpbacks were hunted to near ­extinction in the mid-1900s, but after a whaling ban in 1965, the population has grown to between 3,000 and 5,000, according to the Department of Fisheries and Oceans. Part of Passing Cloud‘s mission is to educate guests about the wildlife of the area, and true to that mission, Briony produced a large, notated poster of whale flukes, each identified by its particular markings. We compared our own images with those on the poster with some success. Unfortunately, many of the identifying markings are man-­inflicted, because these slow-moving giants are often injured by boats and caught in fishing nets. A recent law requires boats to remain 300 feet from the whales, but because they remain submerged for extended times, it’s sometimes impossible to avoid them, as we later discovered.

Our days took on a certain rhythm. Early-morning coffee, watching the sun rise over the densely forested hills and islands, then perhaps a Zodiac excursion ashore before a hearty breakfast underway. Breakfast time often included a recap of the previous day and a look at the chart for the current day. Then a lunch stop, and on sunny days, we’d enjoy our meal on deck. After lunch, another shore excursion to go looking for bears, then back to Passing Cloud for a snack before our spectacular dinner. Conversation around the dinner table was always lively, with the crew regaling us with local-history observations and personal adventures.

Because of the inclement weather, preparing to go ashore was always a bit of a mission. First came the long underwear and wool socks. Then layers—on top we had a shirt, sweater, coat and rain jacket, and then added rain pants over jeans. On top of all that were knee-high boots, gloves and hat, and a lifejacket. By the time I was suited up, I felt like the Michelin Man. Glamour was not a priority aboard Passing Cloud.

Of course, no one was required to make any of the shoreside excursions, but even on a couple of the days with heavy rain, we all suited up, climbed into the Zodiac for a short ride, then waded ashore, carefully navigating the rocky foreshore. Either Russ or Liam accompanied us, but Briony, our onboard naturalist, was on every excursion, providing an ongoing show and tell. We learned the ways of the black bears, of the sandhill cranes, and how to prepare special tea from what to the untrained eye were just twigs. She showed us wild blueberries, and on occasions when chef Erin came ashore, she and Briony foraged for sea asparagus and other local greens that later that day would grace our dinner plates.

Going ashore was always an adventure. For my inexperienced eye, the trails we hiked were almost impossible to see. But as Russ and Briony led us on these forays into the forest, we learned that these were bear trails, which in itself was a bit disconcerting. We clambered up and down hills, over fallen trees, ducking under bushes and limbs that hung low over the trail.

On one of the more memorable excursions, after landing in a narrow, rocky inlet and wading ashore, with Russ in the lead and Briony bringing up the rear, we hiked to an area known for bears. By this time, the rains had increased the river’s flow and there was hope that the salmon would be starting to make the migration upriver. And if that were the case, then the bears would be ready and waiting for them.

We broke through the dense growth and found ourselves high on a bank overlooking a raging waterfall that tumbled into a rocky pool. This scenario, we learned, was ideal for watching for bears. As we sat quietly up among the trees and waited, a black bear silently materialized on the rocks below us. It ambled along the riverbank and made its way to the pool, where it seemed to contemplate the situation, and then leaped into the water, apparently searching for salmon. As we sat in awe, the bear clambered ashore and spent a while exploring the area. And for a heart-stopping minute, it looked like it was going to climb the bank to depart on the bear trail we had just used. “Just move back from the trail and stay completely still,” Russ told us. The bear seemed to consider whether to come our way, and happily, it chose to go back the way it had come.

Although we weren’t lucky enough to spot a Spirit Bear during our time aboard, we did spend time watching a mama grizzly bear and her three cubs foraging and fording a wide stream to pick wild apples, watched over by literally dozens of eagles that roosted in the trees overlooking the feeding sites. The three cubs acted like typical youngsters, roughhousing and rushing flocks of seagulls nearby, causing them all to take flight.

The area we sailed was so remote that on a couple of late afternoons, coming into our overnight anchorage, we almost felt affronted by the sight of another boat there before us. And traveling through the narrow channels and fjords, we seldom saw any other vessels, so when we spied the Alaska Marine Highway ferry that runs between Port Hardy and Prince Rupert heading our way, we were like school kids, waving to it as it traveled south.

Twenty-plus years ago, this vast area was threatened by overlogging and decimation of the First Nations that have called it home for centuries. During those years, a historic agreement was reached between the B.C. government, the First Nations and environmentalists, which is a road map for other regions of the world. Collaboration resulted in the 2016 Great Bear Rainforest Land Use Order and Great Bear Rainforest (Forest Management) Act, a consensus-based decision-making model that works toward protecting both the cultural and ecological heritage for future generations.

Klemtu, the only community we visited, is a beneficiary of the historic agreement. We were fortunate to visit the longhouse and hear the history of the Kitasoo tribe of Tsimshians, originally from Kitasu Bay, and the Xai’xais of Kynoch Inlet, people who make the enclave their home. And we toured a community-development project, the Spirit Bear Lodge, where our one trinket-hungry crewmember was able to buy a memento. Klemtu is accessible only by boat or seaplane, and very infrequent ferry service.

The Great Bear Sea is teeming with life both above and below. At last count, 210 species of plants, 80 types of birds, 190 marine invertebrate species, 50 fish species, 20 kinds of mammals and reptiles, and 120 different kinds of seaweed are found in this magical place. We cruised the shoreline and meandered through the rocky channels, some so narrow that Liam spent his time as lookout on the bow, ensuring that Russ avoided the numerous unmarked hazards. We passed by a scattering of huge rocks, covered in Steller sea lions, and hung there for a while, simply observing (and smelling) them as they enjoyed the sun that had reappeared. Being so close to shore, we came close to flocks of sandhill cranes without disturbing them. We sailed with a pod of Dall’s porpoises as they went into a feeding frenzy right off the bow. Salmon swam and jumped at the river entrances, waiting for the rain. And overhead, we saw an ever-changing kaleidoscope of peregrine falcons, bald eagles, sandhill cranes, murrelets, shearwaters, cormorants and oyster catchers.

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On our penultimate day aboard, the weather cleared, the sun came out, and the forests and horizons that had looked dark and forbidding lightened up as we sailed under clear skies back toward Bella Bella. It felt so good: the sun warm on my face and the boat so responsive and alive as I drove it to our final night’s anchorage.

Picking my most memorable moment of the trip is difficult. There were so many amazing sights and sounds, but being a Pisces, I have to say that one particular encounter is first and foremost in my memories.

We had numerous humpback whale sightings during the trip, and they were always a thrill to see. But about halfway through the journey, we saw a pod off in the distance as we cruised north. Suddenly, we were surrounded by several of them, really close, almost within touching distance. Russ immediately shutdown the engine, and we simply drifted for an hour or more, with whales cavorting all around us. They came up alongside, rolling slightly, one eye checking us out, then made a slow move underwater, sometimes directly from port to starboard, beneath the boat. Standing at the stern, I watched in amazement as the wheel turned all by itself as the whales brushed against the rudder. Standing there, getting completely drenched in the spray as the humpbacks blew close aboard on either side, I felt as close to nature as anyone could ever be.

Then, sadly, as if on cue, they all sounded, and we were left alone on a silent sea with our most amazing memories.

*Susan Colby is an independent photojournalist and editor who follows the sun, avoiding winter at all costs, while writing about sailing, travel and craft distilleries. *

Heading For Outer Shores

Passing Cloud is a William Roué-designed 71-foot schooner, built in 1974 in Victoria, British Columbia, by Brian Walker. Although designed specifically for cruising, it proved to be surprisingly fast, winning many races in the Pacific Northwest, including the 1984 San Francisco Master Mariners Race, the first non-American boat to do so. Considering Roué also designed the famous schooner Bluenose, this wasn’t surprising. Passing Cloud logged thousands of miles over the years, down the West Coast and south to Tahiti, before returning home to British Columbia, where in 2012 it was bought by Russ Markel, founder of Outer Shores Expeditions, a small-ship, niche-adventure travel company operating wildlife, wilderness and cultural expeditions in British Columbia.

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Sailor and businessman Troy Sears is heading out on an epic nautical road trip that might not end until he’s circled the globe with America, a replica of the schooner that gave the America’s Cup its name.

Sears will leave San Diego on Tuesday evening on a tour that will take him to yacht clubs and races up and down the East Coast and then to the Caribbean. His calendar is largely booked through the final race of the America’s Cup in late June 2017 in Bermuda.

From there, he plans to head to Europe and points beyond.

“I’m hoping the tour will take me all the way around the world,” Sears said. “If I go all the way around the world, I’d end up in San Diego.”

At the very least, it’ll be a voyage of a lifetime for Sears, 53, whose company, Next Level Sailing, has operated America’s Cup boats for charters and whale watching trips since 2003.

“This is the only time in my life I will be doing it,” he said. “If you only go once in your life, you want to touch as many clubs and organizations as possible.”

Sears, an America’s Cup aficionado who has had a relationship with two-time defending cup champion Oracle Team USA, visited 34 yacht clubs with his 139-foot America on a West Coast tour last fall.

The purpose of the tours is to generate awareness of the 35th defense of the America’s Cup. While the cup is still held by San Francisco’s Golden Gate Yacht Club, the racing will be in Bermuda.

America is scheduled to make more than 100 stops along the East and Gulf coasts between May 7 and just before Thanksgiving. After traversing the Panama Canal, Sears will arrive in New York just in time for the America’s Cup World Series regatta. His 2016 schedule will end with a stop at the Ernest Hemingway Marina in Havana. Then it’s on to the Caribbean and finally Bermuda for the America’s Cup.

“I have come to learn there is a millennial generation which does not know about the event at all, and a baby-boomer generation that has a huge variety of emotions,” Sears said. “They range from being super excited about the catamarans that are used today, to wanting to see the cup remain exactly the way it’s been since they’ve been alive. They love the boats that have been sailed in the cup, the monohulls, since World War II.”

The original America was built to showcase the superiority of American naval architecture at the Great Exhibition in London in 1851. It beat a fleet of British ships around the Isle of Wight in 1851 to win the trophy that became the America’s Cup.

Read the full story here.

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