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The City Dock liveaboard ambassador

The City Dock liveaboard ambassador

Every winter the City Dock basin in Annapolis, Md., takes on a totally different character when cruising liveaboards move in with their salty vessels, looks and mannerisms. They hunker down and hibernate in dimly lit, cave-like cabins to wait out the cold spell and build up fat reserves before disappearing into the wild again come spring.

Not so long ago rugged watermen who slept in their narrow workboats and in sailing, oyster-dredging skipjacks kept an open channel cleared of ice with their frequent comings and goings. But last December was a mild one with little ice, not one resident workboat and damn few “arshters.” There are, however, the familiar cruisers wintering over.

Because of their annual arrivals Nov. 1, visitors to the downtown waterfront are treated to a genuine nautical experience that survives beyond the trendy boutiques, restaurants and souvenir shops. To this end, landlubbers strolling the dock had a chance to ask the outgoing Brian Guptil, 61, a salty cruiser from Seattle: “Do you really live on that thing?”

He sure does, but soon enough he and others like him will be replaced come spring by far less colorful kayakers, dinghy rowers, weekend warriors, dayboaters in runabouts, powerboaters on poker runs and muscle-boaters throttling down while parading in and out of what has become known as “Ego Alley.”

A former Coast Guardsman, Guptil often holds court from his perch in the cockpit of Cayenne, his red 1985 Freedom 44 cat ketch. The boat is tied beam-to to the bulkhead in front of the dockmaster’s office, just across from Fawcett Boat Supplies, one of his frequent hangouts. Guptil mills about his close-knit waterfront neighborhood and has become known as a sort of maritime ambassador of good will because of his friendly, talkative nature. His full beard gives him a seagoing air, and goes with his bearlike physique. He is obviously a cruising sailor and cannot be mistaken for a tourist by a tourist.

When I stopped by to introduce myself in late December, I shouted, “Cayenne!” and Guptil came bounding out from his cozy cabin. He was wearing flip-flops, light clothing and a great, welcoming smile. “Come on aboard,” he said.

His cabin exudes that distinctive, mixed aroma generated by a longtime liveaboard, enhanced by faint diesel fumes, accumulated laundry, the organized clutter of a waterway drifter, and his own human presence.

A non-smoking beer drinker, Guptil sleeps in his forward double or aft double berth, does a little cooking and a lot of reading, and monitors his amusing, informative Web site (, with little regard for spelling but much attention to thought.

Known as the squire of Dock Street, this cruiser has made a lot of friends — both on and off the water — since tying up Nov. 1. During the holidays, his boat was glowing with Christmas spirit, as lights outlined the sail area and a string of red along the port rail and green on starboard outlined the boat. The vessel afforded a ringside seat for the annual lights parade that turned into and out of Ego Alley, and guests gleefully came aboard and participated in the event.

“It’s my first stay in Annapolis, and I love it,” says Guptil. “I have never seen so many cruising sailboats in one place. In Seattle, boats are spread out. Being a people person, residing on this nautical Main Street is perfect for someone of my nature. I enjoy telling my story and promoting the liveaboard lifestyle, even though I know some people find it strange.”

I sat and chatted on the starboard settee in Cayenne’s main cabin, opposite Guptil’s preferred position in one of two revolving easy chairs, a Dell laptop at his side.

“I have a busy ‘rant-and-rave’ link on my Web site open to political comment that may offend some because I’m an atheist pontificator who is anti-Bush and anti-Iraq War,” says Guptil, who considers himself a “centrist, not a radical to the left or the right.

“I want to try and bring some philosipy [sic] to politics,” he says, poking fun at his spelling weakness, which becomes apparent after visiting his Web site. “It sure seems to me that we need to thing [sic] a little past the sound bites.”

Politics aside, Guptil joined Singles on Sailboats and cruised Chesapeake Bay last summer with members. His “home port” often was the Magothy River, anchored inside the Dobbins Island bight, a hodgepodge of active boaters.

“I like being among people, not away from them,” he explains. “I would just hop in my kayak, paddle around and make friends.”

A daily visitor to Fawcett Boat Supplies opposite his boat, Guptil has become a welcome visitor … and customer. He bought a stainless-steel Force 10 diesel heater at Fawcett’s but had to wait seven weeks for delivery. “It’s difficult to enter that store and leave with nothing,” he says.

Guptil arrived in Chesapeake Bay last June from New Orleans, where he had spent a year and a half working on his newly purchased boat. “I was hanging out for the summer in the San Juan Islands when I found Cayenne on the Internet, sold my Freedom 36, and moved to New Orleans,” he says. While in the Big Easy he rebuilt the engine, and the plumbing and wiring systems.

“Oh, I have many other things still to do, but then there are always other things to do on older boats,” he says. The best way to keep up with boat work is to become a liveaboard and have it all at hand, ready to pounce when the urge strikes.

Long divorced — and with two children and four grandchildren back in Washington who are “into horses, not boats” — Guptil has lived on power- and sailboats for a third of his life. He did a nine-year tour with the Coast Guard as an enlisted man, and 27 years with Boeing, working in electronics.

He lives on pensions, investments and modest inheritances. “I am thrifty and have an anchor that works, which prevents me from spending money recklessly and keeps me away from marinas and boatyards when cruising,” he says.

Traveling up the Bay last summer with two crewmembers, he was amazed by the hospitality he received when he stopped off in the Western Shore village of Reedville, Va. “A stranger came up in a small boat and offered the use of his dock, power hook-up and a car,” he says. “I couldn’t believe it. That sure wasn’t the reception I got in Baltimore, where my crew jumped ship. I just turned around and left.”

At the City Dock, Guptil pays $5 a foot per month, which includes utilities. He has the use of head, shower and laundry facilities, and frequents nearby Armadillo’s Bar and Restaurant because it serves his favorite beer, Sierra Nevada. “The only problem is there’s no convenient place to buy groceries,” he says. “I have to take a bus to get to the nearest food store.”

Come April 1, when his time is up at the City Dock, Guptil is unsure of his next destination. “I have no plans,” he explains. “I have a developing relationship with a woman here, but I don’t know where that will go, if anywhere, or where I will go. Maybe north to New England for the summer, or maybe the South Pacific. I hear they have fine beer in Australia.”

Guptil can be reached by calling (206) 818-3203 or e-mailing

Jack Sherwood is a senior writer for Soundings and is based in Annapolis, Md.