A Cruising Life in a Boating Culture

Ted Conklin, right, aboard America, a 75-foot Trumpy. Above, America cruising off Sag Harbor.

Every morning, Theodore B. Conklin III wakes up at 6 a.m., happy to be alive.

He watches the sunrise and walks over to the Bagel Buoy for his newspapers and coffee, before heading over to The American Hotel to open for the day. When it’s up and running, the hotel owner sits on the porch and reads the papers, tries his hand at the crosswords, and strikes up conversations with passersby.

“It’s a wonderful way to live your life,” he mused during a recent telephone interview. “It’s an amazing feeling, living on your boat.”

The 75-foot, three-bedroom motor yacht Americais officially off the charter market for the summer, while Conklin calls the Trumpy wooden houseboat home, he said.

“Next week, we’re going up to Quebec; we’ll make it back in three weeks,” he said. “We have an absolutely spectacular captain, which is critical in this kind of boat. If you have a great doctor, a great lawyer, a great wife and a great captain, you’re all set.”

Not to mention a great yacht club, he added — pointing specifically to the Sag Harbor Yacht Club.

“I’ve been a member for 30, 40 years,” Conklin said. “I’m lucky enough to have probably one of the nicest slips in North America, right in front of the clubhouse at the yacht club, with the sunset every day, and Sag Harbor itself is a wonderful harbor. It’s a great bonus that work is just a couple blocks away.”

Nestled in the heart of the village — located at 27 Bay Street — the Sag Harbor Yacht Club is among the oldest in the nation, dating back to 1899, though its quaint clubhouse didn’t become a village fixture until 1914.

With just 150 members as of May, the club is tight-knit, by design and matter of preference, as well as practicality, according to secretary and treasurer Chris Remkus.

“It’s not a big club. We hope one day to have a big clubhouse, but for now, that little one on the dock is good,” he said with a lighthearted laugh. “It’s about the camaraderie of boating. It’s a real mixed group of people. There’s a lot of local members and a lot of people who have made it their boating home in the summertime — who were transient that now come and stay at our docks, and have become friends and actual members of the club.

“While we have a lot of local guys, there are people from different parts,” he continued. “We have some who are very wealthy — billionaires — down to people who are very blue collar. It’s a real mix of people, kind of a whole melting pot. We do try to keep it very local, and that’s the vibe and feel that all the members like.”

After losing two boats on moorings, a slip at the Yacht Club was a no brainer for New York-based Ian Thomas and Cindy White. The longtime boaters took up sailing together in 1990, first buying a 15-foot, second-hand Clark dinghy, trailing it all around the end of Long Island and exploring the waters between Gardiners and Robin Islands before a nor’easter swept it away after a couple years of fun.

Then, they replaced it with a 20-foot, second-hand O’Day Sloop — Nirvana I— allowing them to explore as far as Montauk. It would be the last boat they could store in their garage, and unstep the mast themselves.

Nirvana II was a lightly used, 33-foot Comar Sloop, with beautiful rosewood down below, but not much of a speedster. She would take them cruising to Nantucket and Martha’s Vineyard, “but it took a long time to go nowhere,” Thomas said. After she came ashore in front of their house on the water in North Haven, following another big nor’easter, they sold her and traded up for Nirvana III, a commissioned, 46-foot Hylas sloop.

They would sail more than 65,000 nautical miles together — to Bermuda four times, the Caribbean, Chesapeake, Maine, Nova Scotia, Quebec, and Newfoundland and Labrador, to name a few — safely carrying them through two hurricanes and one waterspout, almost exclusively two-handed by Thomas and White.

“My favorite place is Sable Island, 150 miles from Nova Scotia in the middle of the Atlantic Ocean,” White said. “It is a 25-mile-long-by-1-mile-wide sand spit, which is constantly changing shape. You have to obtain a permit from Parks Canada to visit three months in advance, specifying the exact date of your visit, which is limited to 8:30 a.m. to 4.30 p.m.

“In Nirvana III, we had to sail overnight in both directions with a right whale greeting us at dawn and a pod of bottle dolphins bidding us farewell,” she continued. “We had to anchor in the shifting sands and dinghy to beach for our briefing. Zoe Lucas, who has spent 40 years on the island, gave us a wonderful insight into the largest colony of gray seals in the world, the 500 wild horses who inhabit the island, the large tern colony, and all the flora. In one day, we experienced everything from sun to torrential rain and fog with gale force winds at times. The anchor held!”

After nearly 20 years, the couple reluctantly sold her and bought a 42 Sabre Salon Express powerboat — Nirvana IV— and, last year, celebrated the 375thanniversary of Montreal on board, navigating 60 locks, the Erie, Champlain and Chambly Canals, plus the East River and the Hudson, dodging ferries and the seaplanes at peak time on a Monday morning.

This summer, they will return to the Chesapeake and Albemarle Sound in July and then explore Maine and the St. John River in August, Thomas said.

“If you survive nearly 30 years of living three months every year on board a small craft alone in some of the world’s more isolated areas and still wake up every morning looking forward to spending the day exploring with your partner, you know you are a very fortunate and happy couple,” he said.

Chris Remkus with his family in the Boston Whaler just outside the Sag Harbor Yacht Club.

Remkus and his family of four always look forward to their annual summer getaway to Block Island, he said. The cabin is tight in their 32-foot Boston Whaler, but they always manage to squeeze for the trip they know is ahead.

“Block Island is like Sag Harbor, but a little bit back in time. The people are extremely laid back and I jokingly always say, short of murder, you can do whatever you like on Block Island and nobody would worry about it,” he said. “Everybody gets so hyper around here during the summer — and, of course, everybody gets caught up in their jobs and work around the house. But here you are, 14 miles off of Montauk, and you might as well be 1,000 miles away. You immediately go into vacation mode, and it’s a beautiful place. The Nature Conservancy rated it as one of the last 10 great places on the planet.”

But as much as they boat to relax, they also boat to fish. It is a family tradition going back generations — from Lithuania, where Remkus’s grandfather worked as a commercial fisherman in the late 1800s, to the East End, where his father, Joseph Remkus, was a bayman.

“Fishing, for me, is literally in my blood. The more I do it, the more I get, the more I want to do it,” Remkus said. “It’s almost like gambling, it’s that type of addictiveness. You get a bite, you don’t know what’s on the other end of the line; it could be many different species. I grew up fishing with my dad from a very young age, and we did everything — lobster, crab, eel, scallop — and we would do it around the season. In the winter, we’d go out to the creeks and cut holes in the ice. We would do the whole gamut.”

On the opening day of scallop season, when Remkus was 17, his father asked him to come out — but, being a senior in high school, his son skipped it. So the elder Remkus went out, collected his limit of 10 bushels and headed home to North Haven, where they lived on a creek.

When he walked into the garage, he had a heart attack.

“He died with his boots on,” Remkus said. “I just kind of wish I had gone with him that day.”

The family was left with all of his fishing equipment, as well as mock-ups of a famous little vessel in the late 1950s called the “skimmer” — 9-foot boats with big engines on them, which Remkus and his five older siblings would race around the bay.

“I wanted my boys to have that same type of experience. You couldn’t find those boats any longer; they don’t exist,” he said. “I found one that was basically wrecked and I got plans off of it, so I built one for my boys around 2010, so we still have that. It’s pretty cool to pass that tradition down, and to have them love boating as much as I do.”


For all there is in Sag Harbor, there is even more outside the village — at least when it comes to boating destinations, according to Chris Remkus.

“We live in an unbelievable place in Sag Harbor and I wish more people boated, in general, but people who are already on the water should get out more,” he said. “If you poll people in Sag Harbor and the East End, I would bet you 98 percent of them haven’t been to Block Island. All of these things are here when you look at it, but don’t really take part in it. So I would encourage people to get out and enjoy what we have here.”

Favorite Local Gunkholes

For those unfamiliar with the term, a “gunkhole” is a small, typically quiet cove rarely visited by the boating core, because it’s difficult to find or enter — at least for the uninitiated.

Sag Harbor, and the surrounding area, has quite a few — from Major’s Harbor and Coecles Inlet to Barcelona, Smith’s Cove and Westneck Harbor.

“After a few hours of swimming, sunbathing, stop into the Shipwreck Bar at Island marina for a cocktail and dinner,” Remkus recommends.

Top Destinations

For a day trip, cruise over to Connecticut and snag a slip at Mystic Seaport for the day. The quintessential seaport town is a living museum of sorts — take a tour of the tall ship Charles W. Morgan, walk across the Mystic River Bascule Bridge and gawk at its exposed machinery, or go shopping at the Olde Mistick Village, its cobbled streets lined with trees and flowering pots.

Closer to home, Three Mile Harbor is a great choice — “especially for an evening of fireworks sponsored by the Clamshell Foundation,” Remkus said — or Cherry Harbor on Gardiners Island.

“Pack lunch or grill out while anchored off the windmill,” he said.

Choose a long weekend and head to Newport — a three-hour run from Sag Harbor, on average, Remkus said — or Essex. Stay at Brewer’s Essex Island Marina, he said, and grab dinner at the Griswold Inn, one of the oldest inns in the United States.

But, for the Remkus clan, Block Island is their family vacation, hands down. They have taken a week-long boating vacation to Payne’s Dock every year since 1987, and don’t plan to stop anytime soon.

For those considering Nantucket and Martha’s Vineyard, both are great boating destinations by sail or power, he said, but with a lot of open water, the long-range weather forecast needs to look good — “and you can’t be on a fixed time schedule,” he said.

Here, Fishy Fishy

Coming from a lifelong fisherman, these fishing hole pointers aren’t to be ignored.

For the Peconics, check out Green Lawns, The Brickyard, Buoy 16, Jessup’s Neck, Split Rock and West End, Remkus said.

Near Gardiners Island, the best bets are Crow Shoals, The Fort — also known as The Ruins — Plum Gut, Orient Shoal, Old Silas (Rock), The Rip, The Race, Tobaccolot, and Ceberus Shoal.

From Montauk to Block Island, make a stop at Shagwong Reef, Great Eastern (Rock), Endeavor Shoal, Phelps Ledge, Turtle Cove, Frisbees, The Pinnacles, Southwest Ledge and CIA Grounds.