For many first-time boaters in Maine, the big surprise is not the extreme tides, fog, or granite ledges sometimes right below the surface — it's the lobster traps! Lobstermen set about 3 million traps in Maine each year, and in some places the water seems paved with their colorful floats, just waiting to snag your prop.

Once you gain some local knowledge about lobster traps, their submerged lines, and some experience around them — that happens quickly! — it's just another reason why boating in Maine is so unique. Penobscot Bay, the heart of Maine cruising, offers some of the most spectacular boating to be found on the planet: countless inviting islands and protected harbors to explore, pine-covered mountains, pink rocky coast, quaint fishing villages, high-end tourist towns, and generally moderate prevailing southwesterly winds.

Setting off Down East

Our August Penobscot cruise consisted of a group of sailors who bareboat charter boats someplace different every year. For this seven-day trip, we filled several boats from two charter companies. Our own four-man crew was on Redwings, a comfortable 46-foot center-cockpit sloop.

There's more than enough magnificent coast here to spend a lifetime exploring, though we got a good taste for why this place is so special in a week. But "special" doesn't mean "easy." Navigating the beach bars in the Caribbean is a world away from the challenges that awaited us along the coast of Maine.

"People often believe that if they've sailed in other places that they're a capable sailor in Maine," says Larrain Slaymaker, owner of NorthPoint Charters in Rockport, who's been in the business for almost 35 years. "That's not always the case." This may be changing for the better though. Max Johanson, service manager of Johanson Boatworks in Rockland, the largest charter boat brokerage in the region, says he's seen more boaters prepare by getting certified through ASA, USSailing, Offshore Sailing, or other formal boat and navigational training. "People are paying more attention to the navigation, and we push that pretty hard," he smiles. "Up here, things go ‘bang' instead of 'squish' when you go aground."

Fog, rain, and strong wind can set in anytime, too, but there are countless gorgeous protected hideaway anchorages to tuck in when it does. Luckily, we savored some of Maine's pristine, calm and warm days — clear air, visibility unlimited, as aviators like to say. The cruising season is short up here, too (typically late June through early September), so we prepped for all weather.

Our weeklong circuit hit many of the most beautiful and interesting highlights in Penobscot Bay.

Rockland, where most of our group set out, is the largest harbor and town in the bay and home to Johanson Boatworks, which supplied our boat. It's a busy harbor crammed with power- and sailboats of all stripes, workboats, and windjammers. There are several marinas, including Rockland Landings Marina and Journey's End Marina. North End Shipyard is home to some of the harbor's classic windjammers, a sight to behold.

Rockland deserves extra time to explore, with such attractions as the beautifully restored Rockland Breakwater Light, the world-famous Farnsworth Art Museum, the Apprenticeshop wooden boatbuilding school, and the Sail Power and Steam Museum. Among the big summer events here are the Maine Lobster Festival (July), and the Maine Homes, Boats and Harbors Show (August) — with its beloved World Championship Boatyard Dog Trials.

Camden, just north, is one of the prettiest summer tourist colonies in coastal Maine. It's also a major yachting center, with a busy, well-protected harbor, guarded by Curtis Island Light at the southern entrance. Call ahead if you want a mooring in Camden (Wayfarer Marine manages most of them), or expect to anchor out by the harbor entrance.

This is where our four-man crew picked up our charter boat at the small municipal floating dock, across the harbor from the Camden Yacht Club. With no wind our first day, we motored northeast past Islesboro Island, arriving before sunset at remote Bucks Harbor, a popular and cozy hurricane hole at the northern end of Eggemoggin Reach. But instead of looking for a mooring there, we headed over to the next inlet west, anchoring halfway up fjord-like (and empty) Orcutt Harbor, and were soon sitting down to a dinner of fresh pan-seared Maine scallops and crisp wine, savoring the nearby forest scents and quiet solitude.

The Road To Mount Desert Island

We woke to thick fog, hiding even the nearby shore. After devouring omelets and sausages, we fired up the radar and GPS and very slowly motored out of the harbor with a lookout on the bow for boats, pots, and markers. When the fog lifted, we had a gorgeous view of Eggemoggin Reach, one of the prettiest stretches of water in Penobscot Bay, separating Little Deer and Deer islands from the mainland. On the eastern end of the Reach is the small town of Brooklin, picturesque home to Wooden Boat magazine and its Wooden Boat School, where boaters can visit, along with the revered Brooklin Boat Yard, a custom builder of gorgeous power- and sailboats of classic lines.

Leaving Eggemoggin Reach, we sailed east and crossed Jericho Bay, heading our way through the narrows of Casco Passage and entering Blue Hill Bay, with Mount Desert Island ahead. Just past Bass Harbor Bar at the southern tip are the shallows of Western Way, an easy passage between Mount Desert and the Cranberry Isles for all but the deepest-draft cruisers, and a convenient shortcut to two of Maine's top cruising destinations.

Northeast Harbor, due north, was once known as "Philadelphia on the rocks" for all the blue bloods who summered there. The small town is a short walk up the hill from the marina and offers "Old Maine" village charm. Just west of here is the narrow, deep fjord of Somes Sound.

Nearby Southwest Harbor to the west, the bigger and more protected of the two, is headquarters to such semi-custom boatbuilders as Hinckley Yachts, Morris Yachts, and Ellis Boat Company. Popular sites here include Beal's Lobster Pier, and Dysart's Great Harbor Marina, a sprawling modern facility that's a big draw for cruising clubs and huge private boats sporting uniformed crews and tax-haven flags of convenience. A short walk from the marina is the small village of Southwest Harbor with great stores, galleries, and restaurants.

On the east side of Mount Desert is Bar Harbor, the island's tourist Mecca often overwhelmed by crowds from cruise ships and land yachts. This is the hub for the free Island Explorer shuttle bus that circles the island, making all of Acadia National Park ("the crown jewel of the North Atlantic coast") easily accessible to cruisers from any major harbor on the island. Do. Not. Miss. Acadia.

Closing The Circle

Our third day out, we got an early start sailing south around Swans and Marshall islands, then west into Merchant Row. This is a beautiful maze of dozens of small, remote, and mostly uninhabited islands between Deer Isle and Isle au Haut, with many excellent anchorages surrounded by pink-hued granite fringed in lush evergreens. We anchored that evening in the calm shelter between Camp and Devil islands, just east of Stonington at the southern end of Deer Isle.

If Stonington is a frontier town, as it's been described, then lobstermen are its rough-and-ready cowboys. This is home to more than 300 lobster boats, and the annual Stonington Lobster Boat Race in late July is a big deal.

Early the next morning we cruised past Stonington and dropped south. After several days of dodging lobster pots, the crew of Redwings decided it was time for revenge, so we sailed to Isle au Haut for what turned out to be the sweetest — and most expensive! — lobster rolls of our voyage, consumed at an outdoor picnic table, yards away from the lobster boats that had brought in our lunch just hours earlier. About half of this wonderfully isolated island is part of Acadia National Park, which offers magnificent hiking, a wealth of wildlife, and striking biodiversity. The still-active Robinson Point Lighthouse is now part of a high-end B&B, The Keeper's House. The small harbor here can be too shallow to transit at low tide, so time your visit.

After lunch we headed back out and quickly ran into a chilly fog bank, navigating by chartplotter and sound (the radar having decided to take a vacation), keeping all ears out for bell buoys or other boats, and periodically ringing our ship's bell. With a gale forecast to arrive that night, we sailed for Pulpit Harbor on the west side of North Haven Island, one of the best hurricane holes in Penobscot Bay. There are no public facilities in the harbor, but provisions are available a mile walk away at North Haven Groceries.

North Haven and its larger sibling to the south, Vinalhaven, are part of the Fox Island archipelago and are separated by Fox Island Thorofare, one of the most dramatically beautiful stretches of water in Penobscot Bay. We motored westward past Goose Rocks Light into the Thorofare of rocky islets and boulder configurations, beautiful homes peeking out, and classic windjammers sailing through.

This was our last night at anchor, in the picturesque harbor off Dix Island at the northern end of Muscle Ridge Channel, in Penobscot's southwestern corner. Dix and neighboring Birch Island are privately owned, but boaters are welcome to hike the trails as long as they respect private space and not make campfires.

Our sixth day involved a short sail southwest to the mainland village of Tenants Harbor, an excellent harbor of refuge. Tenants Harbor Lighthouse on the south point appears in paintings by the late Andrew Wyeth and his son Jamie Wyeth — not surprisingly, since the family has owned the lighthouse since 1978.

Early the next morning we sailed back up to Rockland, drifting in light air and a fair tide through Muscle Ridge Channel. The highlight was passing Owls Head Light, one of the most charming — and said to be the most haunted — of all the lighthouses in Maine. It was a short leg back around Rockland Light and into the harbor, where we closed our circle.

We'd stretched ourselves, dealt with 18-foot tides, shrouds of unexpected fog, and sometimes massive obstacle courses of lobster pots. But we'd done it with more laughter than hair-raising drama, and we ate like kings. It was one of the best boating trips of our lives.