Steve Tofield's ultimate guide to cruising in Maine
by Lyman-Morse Boatbuilding 2 May 2019 14:25 UTC

Cruising Maine © lymanmorse.com
Steve Tofield was one of Lyman-Morse's earliest hires: He started all the way back in 1984, after finishing a Master's in Fine Arts, minoring in handheld objects, from the State University of New York at Albany.
He's currently a Service Manager managing the myriad projects that goes on here; but actually, "rock star" sailor, sculptor and nautical problem-solver is the logical human outcome of nearly thirty years of building, racing and piloting boats in and around the Maine coast.
Talking with Tofield about sailing in the mid-coast is a mix of deep conversations about how the local leeward shores compare to those of Southern Ireland's; how to best set downwind sails while still sailing upwind; and the comparative sailing capabilities of Precambrian Viking warships.
"Sailing isn't anything new," says Tofield. "I like the historic part of it. That's why I like cruising in Maine. Once you get a hang for this coast, it is a delightful place to sail." Of course, if you tire of those subjects, get him started on Perry Pears. The man has a young orchard of 140 trees!
To share his love of the area, Tofield sat down and crafted a 7-day cruising itinerary in and around his favorite places in mid-coast Maine. Like many Maine sailors, Tofield has learned that the secret to cruising here is all about keeping things flexible and manageable. Here are his five tips for a smooth cruise:
1. Stick to boats shorter than 55 feet, with no more than an 8' draft
Cruising well in Maine is as much about getting off your boat as it is getting around with it. So, if your vessel is too long or too deep, you can't sneak into the best anchorages. Though Tofield has camped and cruised in kayaks, he recommends a medium-sized boat like a Seguin 44 or one of the various mid-sized comfy motor cruisers. In Maine, less is more.
2. Go with as small an inflatable as possible
It is an absolute must to be able to get ashore by your own devices, which means carrying a reasonable dinghy, with oars or a small outboard. There are no perfect answers here: Towed dinghies tend to swamp. Dinghies on deck, or hanging off the stern, tend to make for boats that are too big or too cramped. Tofield's answer is to pack as small a roll-up inflatable tender as possible and then simply accept that he will be pumping, deflating and rolling. A model Tofield likes is the AL-390 PVC inflatable sport boat.
3. Have a hard navigational backup
Modern chart plotters, radar, and signal beacons are a must in Maine. But so are old-school paper charts, binoculars, pencils, and paper. Tofield likes to keep a running dead reckoning with frequent by-hand log entries to confirm his positional narrative. "The electronics going down is not the time to relearn what a parallel ruler does," says Tofield.
4. Respect the fog
If offshore, Tofield will slog along in the face of zero visibility. But if he is inshore, and it gets foggy, it's better to find some excuse to get something done on the boat and stay at anchor. If scheduling becomes an issue, the Maine coast features surprisingly good bus service. Simply get ashore and hop a Concord Trailways bus or a Cape Air flight from one of the local airports: Owls Head or Bar Harbor gets you to Boston. And come back to get the boat home another day.
5. Have a wetsuit and a sharp knife on a stick to cut fishing gear
Even boats with propeller spurs and good hull designs catch lobster traps. That is a serious hazard. Cheap used wetsuits can be picked up from surfers for pennies on the dollar. Get one that fits and get in the habit of using it daily to bathe, swim and stay clean while you cruise. Steve says the water in Maine is cold, but once used to it, it will keep you young.
Steve Tofield's Ultimate 7-Day Maine Coast Cruising Itinerary
Day 1: As they say "When in Rome"
The rich and famous come from around the world to Penobscot Bay. See why, by heading due east from Camden toward Vinalhaven and through the storied Fox Island Thorofare. But instead of docking near a trendy crowded estate, Tofield recommends pressing on through the passage and sneaking into the absolutely private Seal Bay. This spacious cove is house-free, features a mud bottom ideal for ground tackle and has no cell phone coverage at all. You are free!
Day 2: Dive south for birdwatching on Criehaven and Wooden Ball Island
The tap water on these lightly populated slabs of granite runs salty, and for good reason. The out islands of Criehaven and Wooden Ball are perched on the absolute edge of the Coast of Maine, near Matinicus. Saltwater runs through the very veins of the place. If you find Criehaven Harbor full, and the weather cooperates, Tofield recommends sneaking east and finding a snug spot between Pudding and Shag Islands. Then inflate your dinghy, get ashore, and sense the pounding and primordial pulse of the wildlife and breaking waves. Abandoned Wooden Ball Island, in particular, is worth a stop.
Day 3: Take the offshore run to Frenchboro for a lobster grilled cheese sandwich
The U.S. Census says 61 people live on the coastal outpost of Frenchboro. And the culture there is all about lobstah! Lobstermen work the nearby ledges and Lunt's Dockside Deli serves their catch directly as awesome rolls, dinners, and fish chowder. Just pull into the dock, tie up, and realize that one can really order lobster and cheese in one sandwich. A nice touch is to head to the Post Office and send a postcard, because Frenchboro is so much cooler than France. And then chill on the boat, safe and sound and watch the zillion stars filter out from the night sky.
Day 4: Channel Joshua Slocum and Dead-Recon Your Way to Mistake Island
Though the world's first solo circumnavigator probably did not pass exactly where you are, the 35-mile or so run to Mistake Island, south of Jonesport, is close enough. So, switch off the instruments, break out the paper charts, channel Joshua Slocum, and run a course of about 75 degrees magnetic to navigate your way to the snug anchorage behind Mistake Island. Attentive anchoring is required: Tofield once woke up with his boat angled at 45-degrees, sitting on the bottom, by setting up in the wrong spot. But it's all worth the hassle. Come to this place, on its own terms, and the wooden walkway that leads through pristine raspberry barrens will be your personal boardwalk to a lighthouse that's sits as proud and solitary as Maine herself.
Day 5, 6 and 7: Solve the Windward Rubik's cube of making for home
Tofield figures it will take a good three days of windward work to cover the 90 miles or so back to Camden. He likes to get up early, work inland when the wind is calm and pick his way through the islands, narrows, bars, and reaches. The art and magic of it, is to leverage the lees and eddies of these inland channels to shorten the windward climb back to Camden. And then pick overnighting spots as conditions merit.
No matter the path, Tofield recommends spending the last night in the tiny archipelago between Great Spruce, Butter, and Eagle Islands, north North Haven and east of Islesboro. That way, when you pull back into Camden Harbor the next day, for supplies and a hot shower, you and your family will be changed forever.