Articles /Travel Ideas / Beach & Water Sports

Sailing the Maine Coast: Antique Schooners and the Dream of a Simpler Life

Some men buy red sports cars when they reach a certain age. Bob Tassi had a different idea: buying an antique schooner and offering an idyllic vacation experience to all comers.

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By Matt Hannafin

  Published: Jun 22, 2004

  Updated: Oct 11, 2016

June 23, 2004 -- Let's take a poll: How many of you cell-phone-toting, e-mail obsessed, nonstop 21st-century types dream of going quietly off-line for a while, back to some kind of ideal summertime memory -- you in a sailboat on the open water, cozy bunks and kerosene lamps at night, stars in the sky and quiet all around? Aboard Maine's fleet of old-time schooners, that's exactly what you get, on mostly 3- to 6-night cruises that run from $395 to $875. With most having no engine, little electricity, and only the most basic accommodations, these ships offer their passengers the chance to get away for a few days of pure magic and a reminder of how sweet life in the slow lane can really be.

It was exactly those features that attracted Bob Tassi, 49, now owner of the schooner Timberwind, when he first heard of the fleet in 1998. At the time, Tassi was director of studio operations for Warner Brothers Records in Nashville, recording and mixing artists like The Fairfield Four, Kenny Rogers, and Johnny Cash. But changes in the record industry and his recent marriage had him looking for new challenges.

"Dawn and I had been looking since we got married for some profession we could pursue together, but weren't sure what. Having a sailing background I'd always wanted to get back to a coastal area, and Dawn was originally from Maine. One day, we were watching a TV special about the young craftsmen who were coming into Maine to build boats the old way. One of the segments was about the windjammer fleet, and as soon as I saw it something just tumbled in my head. I said, 'Oh my goodness, there are people actually doing this and making a living and raising their kids on the boat,' and that sounded really wonderful to me."

The Tassis then did what most first-time passengers do, requesting brochures through the Maine Windjammer Association (800/807-WIND, www.sailmainecoast.com), a marketing agency for fourteen independently owned and managed boats, and culling through all the brochures they received in the mail.

"It ultimately came down to the Heritage and the Stephen Taber. I was wanting the Heritage because I knew Captain Doug Lee had built her from scratch, designed her and built her, and I wanted to meet a guy who had done that. My wife wanted to sail on theTaber because there was a picture in the brochure of Captain Barnes pinching his wife Ellen on the cheek, and she said, 'I want to sail with a couple like that.' Naturally, we sailed on the Stephen Taber."

Once aboard, it took the couple only two days to decide it was what they wanted to do for the next stage of their lives.

"We had such a wonderful time. We were both boat familiar, so the spare accommodations didn't bother us a bit. In fact I even laughed, because the fisheye lens they'd used in the brochure made our cabin looked huge, then they showed us to cabin 3 and it was this tiny little box with a curtain on it, and we're right next to the galley pump so when Paul," - Paul Dorr, then the Taber's cook, now first mate and part-time cook on Tassi's Timberwind - "was pumping water in the morning it was right next to my ear. But to me, I would have been disappointed if it had been fancy. I wanted something rustic. It was exactly what we were looking for."

As it turned out, the Taber's owners had discovered windjamming in exactly the same way, doing a week's sail on the schooner Lewis R. French and then putting together a plan to buy their own boat. "So, they understood it when we approached them," says Tassi.

"We hadn't really gotten to know each other that well during the cruise, but we went and talked after and had a frank conversation about what being in the windjammer business was like, and I think they deduced pretty quickly that this wasn't just a whim for us. I had some vacation time left over in October, so I came back and gave them a week of free labor putting the boat away in exchange for more information. We agreed after that that I was going to come back and join the crew in April, the following season. And that's how it all got started."

Tassi signed aboard Stephen Taber as a deckhand at age 44, some twenty years older than the average hand in the fleet. It's taxing work, requiring long hours and sometimes grueling physical labor, all for the lordly salary of $125 a week. "I had a vision of being an owner and a captain, though," he says now, "and very little was going to get in the way of that."

After three years splitting his time between summers hauling sail and the rest of the year recording country legends in Nashville, Tassi had risen to the job of first mate aboard the Taber, and the urge to get his own boat was strong.

"We were in line to buy the Taber. After my first year aboard Ken and Ellen approached us, had us over for cocktails, said, "here's the plan", and laid out a two-year scenario. It was more than we could have ever hoped for. I never even dared to think that something like that would ever happen. They had an eye on retirement and they had discussed it with their son, Noah, but he was in or just out of college and wanted to test out his wings in the world of advertising in New York, and wasn't quite ready to commit to this lifestyle. So we were the heirs apparent, and we gave everything we could, physically and spiritually 'cause we believed the Taber was going to be ours."

It was not to be. Over the course of the next two years the timetable and price became more and more elusive, and eventually Noah Barnes decided to take over the business himself. So, when the opportunity arose to purchase the Timberwind, a vessel the Tassis had admired over the years, they leapt. "The price was right, but it was fraught with all kinds of challenges that the Taber wasn't. The Taber was an established, perfected business. It had already been optimized. They were carrying full boatloads. We felt, looking at the two, we could either wait the extra time for the Taber and be the guys who had everything to lose, or buy the Timberwind and be the guys who had everything to win. And that's the choice we made."

The Timberwind

Built in Portland, Maine, in 1931 as the Portland Pilot, Timberwind spent the first 38 years of her life stationed 18 miles off Portland Head, taking pilots to meet large ships and navigate them in. Strong and handsome, she originally carried twin-screwed engines as well as sails. In 1969 the vessel was finally replaced by a steel powerboat, at which point Captain Bill Alexander bought her, brought her to Rockport, and retrofitted her interior to accommodate passengers, a process that involved removing the engines and expanding her sailing rig. She's been offering passenger cruises on Penobscot Bay since 1970, and has never left Maine's waters.

Despite his years aboard the Taber, Tassi's first year with Timberwind was a trial, both because of the post-9/11 travel downturn and because of the inherent difficulties of maintaining a traditional wooden schooner. On February 15, 2002, with Timberwind at her winter dock, they got an emergency phone call. The boat was taking on water.

"She'd iced in heavily and popped a plank, and had flooded waist-deep on her lower deck. Once we pumped her out I spent the next 18 days pretty much around the clock on the schooner, moving pumps around and keeping her afloat because the harbor was still deeply frozen and we were unable to move her."

"We figured it was going to be a fairly simple repair -- a plank got sprung, we'll replace some planking and do some recaulking and we'll call it good. But when we finally opened her up we found out she was rotten." He shakes his head. "Just rotten. And there was no way to do a simple repair with a good conscience. It had to be a thorough, complete rebuild, and we had no workforce, no materials."

"God it was demoralizing. The first few seconds, I thought 'This is just beyond me; I've finally bitten off more than I can chew.' But that was followed by a voice in my head that said, 'Don't you dare do that. Don't you dare even think about quittin'."

A massive rebuilding followed - a familiar story in the windjammer fleet. "We kept the deck, we kept the wheelhouse, but everything to the waterline down and back is new. And it was really the other schooner captains at the North End Shipyard that helped us through that process. That's where Paul found us again too. He'd been traveling around and caught up with us there and said, 'You look like you need help.' I said, 'You bet' [laughs]. And he just never left, and I'm delighted because he's probably the most capable person in this fleet in terms of being a sailor and all around knowing about schooners. He can occupy any position comfortably, and with skill and expertise. We even gave him a new title: schooner consultant."

Today, with Timberwind in better overall condition than she's been in the past decade, Tassi is optimistic. "She's stronger, sails better, and we have a good crew. That's important. If you don't have a great crew you're not going to have a happy boat and if you don't have a happy boat you might as well stay in." It's all a lot like his old recording job. "I think the best records I ever made were where you hire good musicians and just let them do what they do, and only guide them ever so slightly if they start to get off track."

Windjammer People

"Ideally, the best crew is somebody like Paul who's in this for a career, somebody who you can just close your eyes and count on. Those people are the most valuable; they'll come back year after year and they'll work the hardest, because they understand -- they understand the economics, they understand the work ethic that has to be involved in doing this. It doesn't pay very well, so it has to be for passion."

That passion is everywhere on the Timberwind, and on the Maine windjammers in general, flowing out from the crew to infect the passengers, sometimes in a big way. Robin Mass, formerly a securities lawyer in Manhattan, took her first windjammer cruise ten years ago, coming back every year to sail the Stephen Taber, where she later met Captain Bob. "I was very lucky on my first trip. I fell in with a group of people and we just liked each other. We had great fun and laughed the whole time. I went home and I cried, because I knew I didn't want to live where I lived anymore. I wanted to live here." Two years ago she acted on that passion, relocating to coastal Maine with her sailor beau Chris Moore -- who she met while he was crewing aboard the Taber.

"It got into my heart," she says.

Most passengers know the kind of experience they're signing on for when they book, but most aren't quite prepared for just how rustic it can be.

"Initially, a lot of passengers experience some sense of shock, especially if they're not sailors and don't understand what a boat is," says Tassi. "They have a romantic vision of what it is, and I think despite your best efforts to be honest with them -- to say look, these are really small cabins -- unless you've been on a boat you can't picture that. But, I think that reaction passes quickly. The first night's always a little stiff."

"Something happens to you, though. You can see it in the eyes of people who get on the boat Sunday night and they're very anxious about the accommodations, and claustrophobia, and only two toilets, and then we scare you to death about the toilets not working if you flush the wrong thing, but then suddenly by Wednesday they almost transform. Where they were checking their messages and looking at cell phones, all of a sudden that stuff gets put away, and something gets inside of them, and they become windjammer people. Very few go away unhappy."

So What Do You Do All Day on Board?

"I just throw open my arms and enjoy it," says Mass. "It's so phenomenal. I spend my whole time just looking, just taking it all in."

Exactly opposite to the typical cruise experience, Timberwind and the other Maine schooners sail during the day and anchor in protected coves every night, running their yawl boat ashore in the mornings to let passengers explore small fishing towns or hike on some of Penobscot Bay's 3,000 islands. By day, the schooners sail where the wind takes them, with passengers welcome to help with the sails and anchor, climb the rigging, take a turn at the wheel, scan for seals and whales, or just relax. Often, two or more boats will meet up and take each other on in an informal race, and often one night a week will see passengers debarking onto a quiet, rocky beach for a traditional lobster bake. Meals aboard ship are prepared on wood stoves in rustic galleys and served out on deck, picnic style, as long as the weather cooperates. Expect traditional New England staples such as fresh seafood, chowder, roasts, and Irish soda bread, plus chili, Mexican salads, and the occasional key lime pie.

Cooking aboard a rolling ship presents difficulties. On a recent sailing one passenger asked first mate Dorr, who does double duty as cook when Dawn Tassi isn't aboard, why he kept running back and forth from the deck to the galley. "I'm tacking the pan," he explained, using the term for shifting the sails to take a schooner in a different direction. "I've gone down and found an empty pan in the oven," he explained later. "And I'll think, 'I could have sworn I put brownie batter in that pan.' It just rolls right out. And it's funny, different schooners make the dough react differently in the pan."

You and Me and Baby Makes Three

"Unless you've sailed, I don't think you can account for how a boat gets inside of you, how you will fall in love with the vessel itself, " says Tassi. "Or, you fall in love with the couple that runs the boat. Or a combination."

When they bought Timberwind, the Tassis' intention was that they would operate the vessel as a couple, living aboard in summer with their two children, Will, 8, and Emily, 2. But simple economics have put some kinks in that plan.

"Doing this was about us. It wasn't about me coming up here and sailing and leaving her ashore. It was about both kids being on the boat and the two of us being together. We did it all last year, and we took a big hit economically since she quit working. We didn't feel, with the way things were going, that we could afford to do that this year. She is doing the weekend cruises, and the little touches that she brings to it -- brings to her galley, brings to her vessel . . . you just feel her presence on board. She's a great partner and friend. I didn't get married till I was forty. And I wasn't looking to get married. I thought that whole train had gone by me, especially kids. Now here I am with two little ones and a beautiful young wife and this lovely schooner, and friends aboard to sail with -- so I'm pretty darn happy."

Timberwind is one of the few schooners that accept young children, with a minimum sailing age of 5 though that can be lowered under certain conditions. Last week, Bob's son had a playmate in 6-year-old Mary Hayward of Amarillo, Texas, sailing with her first-time windjammer parents Steve and Martha. The schooner became a whole world to explore, the week an opportunity to use the imagination most kids cede to TV and video games. Picture Mary running up to the captain, imposing behind his salt-and-pepper beard and dark sunglasses.

Bob: How're you doing, dear?"
Mary: "We're playing spies."
Bob: "You are? Who are you spying on?"
Mary: " I don't know!"
Bob: "Just anybody, huh?"
Mary: "We have the rope for it." (Holding out a small loop of rope.)
Bob: "Yep."
Matt: "Gotta have rope if you're a spy."
Mary: "Because you have to slip down into a hole if they see you."

The Details

Timberwind sails 3-, 4-, and 6-night itineraries from Rockport, Maine, through October 6, with prices running from $435 to $835 per person. She's among the most rustic and unmodernized vessels in the schooner fleet, with tiny varnished-wood cabins that sport small electric lights but do without plumbing. Instead, each has an enamel basin, a stack of towels, and a small oak water barrel on a corner shelf. Beds are either bunks or doubles. A maximum of twenty passengers share two communal toilets; an old-fashioned hand-pump on deck dispenses drinking water; and a shower can be rigged up by request. "It's like camping on the water," says Captain Bob. "But without the ants and with better food."

Contact Timberwind at 800/759-9250, www.schoonertimberwind.com. Information on the other vessels in the Maine fleet can be seen on the Maine Windjammer Association's website, www.sailmainecoast.com. You can also request brochures from all the schooners through the site or by calling 800/807-WIND.

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