Cruising to Historic Portland, Maine

For boaters, Portland has been a favorite haven for centuries.

Portland Head Light
Portland Head Light was first lit on January 10, 1791. Lightkeepers and their families lived there until 1989. Jeff Gardiner/Unsplash

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The largest city in Maine was born of fire and water. Portland’s seal shows a phoenix rising from the ashes, a reference to the way the city rebuilt after not just one, but four devastating fires. At the same time, since at least the 1600s, the city’s heartbeat has been its waterfront. Today, that waterfront is a mix of working boats and tourist haunts that’s noteworthy because it’s more restored than rebuilt. Yachtsmen who head ashore will encounter much of the same vibe that existed when sailors stepped off their ships in the late 19th century. About 70 percent of the structures were built back then, making this seaport unusual even within New England. It’s hard to find entire streets lined with Victorian commercial architecture like the ones that still stand today in Portland.

It’s also hard to find such an eclectic mix of museums, restaurants and culture. The historic, shopping and arts districts are all near one another, with everything from a gluten-free bakery and a narrow-gauge railroad museum to an old-fashioned record store. The International Cryptozoology Museum says it has hair samples on display from abominable snowmen. There are open jazz sessions on Tuesday nights at the venue known simply as Blue. At the Broken Crow, tattoo artists can create just about any design a boater might want.

And all of it is surrounded by rich history. Portland Head Light still offers the same views that the city’s defenders looked out upon during the Revolutionary War and World War II. The Portland Observatory is also here—it’s the only remaining historic maritime signal station in the United States, built 86 feet tall by a man who charged ship owners $5 apiece for a heads-up by way of his telescope that their vessels were within 30 miles and heading into the port.

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Today, of course, things are easier with channel 16 on the VHF radio and local marinas, but stepping ashore to explore remains just as much fun.


Located on Casco Bay,  Fore Points Marina has 150 slips for boats from 25 to 545 feet length overall. Mega-yacht owners and crew can request high-speed, in-slip refueling. Dimillo’s Old Port Marina has transient rates that increase with the size of the boat. Yachts 96 feet and larger pay $5.50 per foot, and there are group rates for flotillas of 10 or more boats (of any length overall) that are traveling together. Portland Yacht Services has 128 slips and 18 transient moorings for boats with drafts as substantial as 20 feet. Small sailboat rentals are available here for yachtsmen who want to dock the big boat and head out into the bay for an easy, breezy sail.


Portland’s downtown districts each have a different style. Old Port is the revitalized section of the city, with a working waterfront as well as shops, restaurants and entertainment. Expect to find cobblestone streets, unique boutiques and quite a few varieties of lobster specials on the menus. The Arts District is a few blocks from the waterfront, with museums, theaters and the Maine Historical Society. Smaller galleries and performance venues are here as well, with a mix of fine dining and ethnic restaurants. West End is the place to see architecture, including some of the city’s largest historic homes and camera-ready Victorian neighborhoods. 

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