Portland, ME

The Maine Event

Dock and dine your way through this picturesque New England haven.

It’s easy to pass by Portland if you’re cruising Down East on a rhumb line from the Cape Cod Canal to the popular Boothbay or Penobscot Bay areas. After all, the coastline curves west at Portland, so you might think it’s a bit out of the way. But think again, because Portland—once an industrial town with a hard-working commercial waterfront—has transformed itself into a vibrant city with a thriving art and restaurant scene and some of the best full-service marinas in the Northeast. And Casco Bay, with its handful of small islands, historic forts and iconic lighthouses—not to mention rocky ledges and finger-like peninsulas—offers some of the best cruising in a state already famous for its spectacular cruising grounds.

Portland is charming because it’s the gateway to the real Down East but still has a feel of a small town, even though it’s the largest city in the state with a population of 66,194. With cobblestoned streets rising up a small hill from the Old Port waterfront (the downtown section), almost everything in Portland is accessible and within walking distance, even in a pair of boat shoes. The I.M. Pei-designed Art Museum is easy to find; so are restaurants of almost every description. Indeed, with 230 restaurants in town, Portland has the highest proportion of restaurants per capita of any city in the U.S.—and they’re good. In 2009, Bon Appétit called Portland “America’s foodiest small town.” The harbor, meanwhile, is full of recreational boats, power and sail; old schooners carrying tourists out in the bay; fast ferries; commercial fishing boats; a fleet of working lobster boats—and tons of lobster pots. There are countless reasons why 3.6 million tourists visit Portland every year.

But history has not always been kind to Portland. The first European to land there was Christopher Levett, an English sea captain, who arrived in 1623 with 10 men and a grant of 6,000 acres from King Charles I to start a settlement. He built a stone house for his men then sailed back to England, where he wrote about the wonder of the New World; his men were never heard from again. A subsequent trading village was destroyed by the Wampanoag Indians in 1676, but it was rebuilt and destroyed again by the French and Indians in 1690. During the Revolution, Portland was shelled by the British, and in 1866, a fire during Fourth of July celebrations burned down most of the city leaving 10,000 people homeless.

Today, Portland is easy to find. Coming from the south, pick up the sea buoy 12 miles southeast of Portland and 5 miles off Cape Elizabeth. Round Cape Elizabeth and turn north toward the Portland Head Light, 101 feet above the water. First lit in 1791 with 16 whale oil lamps, it’s the oldest continuous lighthouse in the U.S., now maintained by the Coast Guard. The Portland Head Light marks the south side of the entrance channel; across the way, the 77-foot-high Ram Island Ledge Light marks the north side. Go down the main channel—leave Cushing Island to starboard—1.8 miles to the black-and-white 54-foot-high Spring Point Lighthouse at the end of a long breakwater. Follow the channel in a wide left turn into the main harbor.

Before you enter the harbor, though, you have to make a choice. Tie up at the marinas on your left in South Portland to enjoy the peace and quiet with the Greenbelt Walkway that runs along the shoreline and a swimming beach, plus easy access to stores and restaurants? Or head right to Portland proper, the traditional Old Port marinas, with the trendy restaurants and art district?

If you choose Portland itself, it’s hard to miss DiMillo’s Marina, since it’s pretty much in the heart of Old Port. It’s also a large, first-rate, full-service marina with high-speed fuel pumps, 125 slips and room for yachts up to 250 feet. The marina itself is secure and gated and is in front of DiMillo’s floating restaurant, which was a car ferry in its previous life. The restaurant is big and touristy, but it’s a Portland institution and it’s fun.

About half a mile up the harbor, Portland Yacht Services is another large, welcoming marina with 250 slips. The bad news is that it does not have fuel; the good news is that it’s a short walk from Hamilton Marine, the largest marine supply store above Boston. About two miles up from Old Port, the Maine Yacht Center has 80 slips for boats up to 60 feet. It is a full-service marina with gas and diesel and an 80-ton Travelift.

If you opt for the quieter South Portland side of the harbor, Spring Point Marina has 275 slips and claims to be the largest full-service marina in Maine. It can hold yachts up to 200 feet and is within walking distance of the beach and grocery stores. Joe’s Boathouse there serves lunch and dinner.

Up the harbor a bit, Sunset Marina’s full-service yard with 150 slips accommodates yachts up to 250 feet and offers terrific views across the water of Portland and the skyline. Closer to the Casco Bay Bridge leading back to Portland, South Port Marine is well protected; its full-service yard has 170 slips for boats up to 150 feet.

No matter where you tie up, you’ll want to spend some time wandering around Old Port. For the art scene, walk up the hill from the waterfront to Congress Street and turn left. You’ll find more than two-dozen galleries, plus The Portland Museum of Art. The museum is a treasure with 17,000 works, including an impressive permanent Impressionist exhibit with works by Degas, Matisse, Renoir, and Picasso. If you get tired of the Impressionists, take in Maine favorites Winslow Homer and Andrew Wyeth. If you want a first-hand view of the city, head for the Portland Observatory at the top of Munjoy Hill. Built as a signal tower in 1807, the 86-foot-high wooden tower today affords an unbeatable view of Old Port, the harbor and Casco Bay.

If you’re hungry you won’t go wrong at Street & Company on Wharf Street in Old Port for fresh seafood—if it’s crowded you can eat at the bar. For a different atmosphere try Grace, a new restaurant in a 150-year-old Gothic Revival Church with soaring stained glass windows—the menu is American, the experience is unique. Fore Street Restaurant is only a block up from the water; with its wood-burning oven and a menu filled with Maine-centric seafood, meat and game, it has been praised by Gourmet. For a total change of pace, head for Becky’s Diner on the Commercial Street waterfront. A true diner, Becky’s opens at 4AM every day except Thanksgiving and Christmas, so working lobstermen can have an early breakfast, and stays open until 9PM. Try the homemade chowder or, needless-to-say, the Fisherman’s Platter.

If this is your first trip to Portland, go 20 minutes up the road to the L.L. Bean Flagship Store in Freeport, an iconic Maine institution. You don’t need to hurry as Bean’s is open 24 hours a day, 365 days a year.


DiMillo’s Marina
1 Long Wharf
Portland, ME 04101
(207) 773-7632 • dimillos.com/marina

Maine Yacht Center
100 Kensington St.
Portland, ME 04103
(207) 842-9000 • maineyacht.com

Portland Yacht Services
58 Fore St., Portland, ME 04101
(207) 774-1067 • portlandyacht.com

Spring Point Marina
1 Spring Point Dr., South Portland, ME 04106
(207) 767-3254 • portharbormarine.com

South Port Marine
14 Ocean St. • South Portland, ME 04106
(207) 799-8191 • southportmarine.com

Sunset Marina
231 Front St., South Portland, ME 04106
(207) 767-4729 • sunset-marina.com



Becky’s Diner
390 Commercial Wharf, Portland, ME 04101
(207) 773-7070 • beckys.com

Fore Street Restaurant
288 Fore St., Portland, ME 04101
(207) 775-2717 • forestreet.biz

15 Chestnut St., Portland, ME 04101
(207) 828-4422 • restaurantgrace.com

Joe’s Boathouse
1 Spring Point Dr.
South Portland, ME 04106

Street & Company
33 Wharf St.
Portland, ME 04101
(207) 775-0887 • Streetandcompany.net


L.L. Bean Flagship Store
95 Main St.
Freeport, ME 04032
(877) 755-2326 • llbean.com

Portland Museum of Art
7 Congress Square
Portland, ME 04101
(207) 775-6148 • portlandmuseum.org

Portland Observatory
138 Congress St.
Portland, ME 04101
(207) 774-5561• portlandlandmarks.org/observatory


By Peter A. Janssen, Southern Boating Magazine August, 2014