OpSail’s origins, O’Brien notes, come in part from the idea of a changing nautical word: the last official working, cargo-carrying tall ship had recently gone out of service when the event was conceived. “So the concept was: Let’s gather these majestic ships before they disappear off the face of the earth forever,” O’Brien says.

That forecast has not come to pass—if anything the numbers are up, at least ceremonially. A mere 16 tall ships showed up OpSail’s 1976 bicentennial event, a paltry turnout when compared with the 25 that will sail in this year for the semiquincentennial. Commodore Harrington says, “This is going to be OpSail on steroids. Just a buzz of activity that whole week.”

How to experience it

Once moored, the ships will open up to the public, inviting spectators aboard to meet the sailors and wander the decks. Among them: Romania’s 88-year-old Mircea, which will again journey from the Black Sea to Brooklyn Bridge Park under the watch of its mustachioed figurehead, contributing to Mircea’s faintly piratical vibe. “It is kind of classic. Not sure we can promise any peg legs or Captain Hook though,” Commodore Harrington said.

The most ideal perch for the procession lies just west of Brooklyn. O’Brien will be stationed on Governors Island, where he once cut his teeth as a young Coast Guard officer and where NBC—including The Today Show—will broadcast the beauties for six hours. “Between the Statue of Liberty and Governors Island’s southern tip, there’s this pitch point where the channel gets narrow and the tall ships seem like they’re right on top of you,” he said. “Great for the cameras.”

Elissa is the festival’s oldest ship—and also one that civilians can actually board (for a price).

Galveston Historical Foundation

The festival’s oldest ship, Elissa, happens to also be one of the few Class A vessels upon which spectators can actually board early that morning and effectively participate in July 4th’s parade of sail up and down New York Harbor. The 50 available spots aboard this surprisingly seaworthy ship from 1877 run around $10,000 a pop including fees.

Texas’s official tall ship hasn’t been to the city since 1986’s OpSail, when Captain Ryan Bradfield was just two years old. This year, he’ll be managing Elissa’s crew of 42, and overseeing rigging maintenance en route. “I’m kind of the ringleader of this circus,” he said. “We get underway from Galveston’s seaport mid-May.”

After the parade, Captain Bradfield and his Texan crew will tie up at Lower Manhattan’s Pier 36, then open the ship to the public for a little après-parade revelry—Texas-centric fare, live music and drinks, including Elissa’s namesake IPA brewed by Houston’s Saint Arnold Brewing Co.

Another ship, Germany’s Gorch Fock, will make the Atlantic crossing once more—only this time Chris O’Brien’s teenage daughter will be aboard. Is the former Coast Guard officer envious? “As a sailor I am very jealous. And her mother is terrified,” he said, laughing. “I’m not. It’s going to be the experience of a lifetime.”

As the sun descends behind the Sierra de la Giganta mountains, I join the end-of-day procession to Loreto Bay National Park, a protected marine area in the Sea of Cortez. Fisherfolk, families, and out-of-towners stroll the Malecón, a mile-long esplanade that traces the water, watching as the sea turns the same sherbet hues as the evening sky. Seabirds dive-bomb for their dinner, and when a gray whale spouts remarkably close to shore, I hear myself gasp.

The seaside village of Loreto, five hours north of the Baja California Sur capital of La Paz, is still the type of one-traffic-light Mexican town whose cobblestone streets are lined with family-owned restaurants and cafés. Papel picado, a vibrant folk art made from cutting elaborate designs into sheets of colorful tissue paper, and lucha libre masks decorate the main drag. The Baroque-style Mission of Our Lady of Loreto, founded in 1697 by the Jesuits, is a point of pride around which the community orbits.

Loreto has had the government designation Pueblo Mágico, given to towns with cultural or historical significance, since 2012, and has managed to avoid the chain resorts, tour buses, and clubs touting tequila poppers so common in other coastal Mexican destinations. Instead, tourism has grown slowly—there are now six direct flights from the US and Canada—thanks in large part to conservationists’ efforts to keep the town and the surrounding sea from being loved to death.

Before my visit to Loreto, I heard the bay referred to as the Aquarium of the World. I figured it was marketing-speak until meeting Ginni Callahan, the owner of Sea Kayak Baja Mexico. She explains that the bay is the preferred breeding ground for dozens of marine animals, including giant polka-dotted whale sharks, blue whales, dolphins, Mobula rays, and thresher sharks. In the 1990s, when residents saw the impact of overdevelopment farther south in the state (like dozens of whale watching boats chasing a single mom and calf), as well as the environmental impact of widespread commercial fishing, they lobbied the Mexican government to create a national park. Now also a UNESCO World Heritage Site, Loreto Bay National Park is made up of 244 islands fringed by turquoise waters. It is home to 39 percent of the planet’s marine mammal species. Locals also created a citizen advisory board to advocate for the park. Decades later, most of Loreto’s outfitters, including kayak guides and tour boat operators, encourage voluntourism: On the multiday kayak and camping adventures that Callahan leads, guests monitor wildlife and help clean up beaches.

One morning, with my mask and snorkel in hand, I tour several of the bay’s uninhabited islands with Luxury Baja Sailing, a tour company with a fleet of plush catamarans that cruise throughout the Sea of Cortez. Within minutes a friendly pod of dolphins begins frolicking about our boat, spinning and leaping over the wake. Nearby, a humpback mom and calf pop up, and rare birds such as blue-footed boobies and magnificent frigate birds perch on nearby island cliffs. Our captain tells us this is a slow day.

We’d just left port, mainland Scotland fading behind us, and were sailing into soft yellow sunlight. The sea was the dark silvery blue of raw denim, and the wind, for now, seemed settled, unshifting. “Here they come,” said Mungo Watson, our boat’s skipper, with deadpan calm, hands on the helm. On deck, the crew and I turned to survey the horizon, then gingerly moved toward the bow of the boat and looked down. “No, not porpoises—dolphins,” Watson continued. “For some reason, and still nobody really knows why, they absolutely love boats.”

It was the storybook start to our voyage that began only an hour or so earlier at the marina of Mallaig. Eight strangers had climbed aboard Eda Frandsen for a more-or-less unscripted salty-dog sailing adventure around Scotland’s Inner Hebrides. Our crew were the boat’s recently wed co-owners, Watson and Stella Marina, experienced sailors who bought the 1938 Danish gaff cutter in 2020 and now run trips out of Cornwall and the west coast of Scotland from April to September. Some, such as the nine-night passage from Falmouth to Oban, probably require more sea grit than, say, a slow long-weekend sail along the Cornish coast. But none of them call for any sailing experience, they reckon. Which is lucky because I had zero. Nothing.

We all had different reasons for being there: some to see Scotland in summer without joining the conga line of Glencoe-bound camper vans; others for the heck of it. “I just like old boats,” said David, my affable bunk buddy. Fair enough. I was there to get into the hard-to-breach orbit of offshore sailing, a world that has stubbornly few points of entry, except for those who know someone with a boat or have pots of cash. Its reputation for exclusivity doesn’t help either. “The elitism in sailing is undeniable,” says Marina. “We’re absolutely trying to escape that. That’s one of the reasons we set up Eda Frandsen: to introduce people to the beauty of being at sea. To open sailing to everyone.”

By late afternoon we’d arrived at Eigg (population: 83), a small, flat, tennis-court-green island with a single peak. The sun was slipping downwards and on the horizon distant mountains turned pale shades of lavender and rose. Small sounds assumed an intense clarity as a deep calm emanated from the nearby land: the lapping of waves and the soft clatter of cutlery. This was the spiritual start of my trip. I was at sea. Life was good.

It would get better. Below deck we dined by candlelight in the cozy wood-finished galley on fresh langoustines, mussels, and chilled rosé. Marina, who spent much of her career as a chef on superyachts, is an immensely good cook. “We’re like a food trip with some occasional sailing thrown in,” said Watson with a gruff wit, half joking. More wine flowed, then whisky. The evening finished in my just-big-enough bunk (comfier than expected) with the relief that there were no tricky people on board. Sailing involves close contact. A single asshole, I’d been warned, can equal agony.

The next morning we left the shelter of the bay and forged into a far less hospitable ocean—not quite bad tempered, but not far off. “Lumpy,” said Watson, who never seemed to run out of words to describe the sea: pitchy, squally, swirly. Passing the moleskin-grey volcanic peaks of Rum, one of the Small Isles, on our starboard side, the boat lolloped towards another, Canna, where we went ashore and hiked to its eastern tip to watch puffins before looping back to the bay for a beer at Café Canna, a tiny, remote restaurant that draws sailors from across the archipelago.

Our days passed like this: At breakfast we devised a plan, then sailed on a changing sea, before dropping anchor in an out-of-the-way spot that would take days to reach by any other means. One afternoon we hiked around Rum, peering into the windows of the decaying Kinloch Castle, an Edwardian red-stone mansion. We jumped from the boat into the dark glassy waters of Loch Moidart as the sky turned pink over Eilean Shona—Vanessa Branson’s island—while seals (“waterproof dogs,” quipped Watson, affectionately) looked on from an islet. On the Knoydart peninsula we sipped beers at The Old Forge, Britain’s most remote pub.

I love being on water. Mind you, I didn’t say I love being in the water, that’s a completely different story. There’s something about being near a body of water or sailing on it that makes me feel like I can accomplish anything. As my friends can attest, I’m prone to seeking out a sailing tour on most of my vacations. What better way to relax than to bask in the sun, listen to the sounds of the waves, enjoy a drink or two, and meet new people?

I only had 48 hours in Split, Croatia so I had to maximize my time and I knew one of my activities would involve a boat tour. Split boat tours are quite popular. As the largest city in Dalmatia, Split sits on the eastern shore of the Adriatic Sea and is a great jumping-off point to the Adriatic Islands. Travelers can book a sailing excursion, private or with a group, and sail around smaller islands off the coast of the city.

As a solo traveler, a boat tour is one of my favorite activities. It’s a great way to meet people and experience adventure with a group. The tour I originally planned was canceled due to bad weather so I decided to go to Trogir, a UNESCO World Heritage Site 40 minutes west of Split. While in Trogir, the weather cleared up so I decided to look into options after all. Since I was running out of time in the day, the easiest thing for me was to start searching through my Airbnb app and filter through tours that would be leaving in the afternoon. That’s when I found Ivan. Not only did Ivan respond to me so quickly but he was completely accommodating of my last-minute request to join the tour that day which had one spot left.

The experience with Ventos-Nautic seemed perfect. I booked the ticket and ran to a nearby shop for a bathing suit and towel and made my way to the meeting point at Kamerlengo Castle. The boat was a small speedboat and there were only 10 of us on the boat. Mostly, there were couples, but also a family from Germany with a young daughter visiting Croatia for the first time. Our captain, Ivica, introduced himself, told us to follow his rules, have fun, and we were off.

Pulling away from Trogir, for the next five hours we basked in the sun and swam in the sea, making stops at Krknjasi Bay and along the coastlines of two islands, Šolta and Čiovo. After a 20-minute speedboat ride, we arrived at Drvenik Veli., also known as the Blue Lagoon. We pulled into crystal clear waters where we got off the boat and got a chance to walk around, visit the shops, or grab a snorkel (which was provided on board) and try to find the slippery fish that occupied the bays. Our second destination was a fishing village called Maslinica on the island of Šolta dating back to the 15th century. The village received an award for the best tourist destination in the Adriatic in 2012, and in 2017 won a national award as the best authentic coastal destination. While we only had 45 minutes in the village, I wandered the streets picking up an ice cream along the way and hiding from the intensity of the sun so the dessert wouldn’t melt too quickly in my hand.