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Photos by Dori Arrington

Portland, Maine

Lighthouses, fine eateries, art are among the many things that make this Down East destination hard to walk away from.

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Our first visit to Portland, Maine, was a one-night stop while traveling south from Nova Scotia. The next time we were cruising the Maine coast we stopped in Portland for four days. On our most recent New England adventure, we booked a stay at DiMillo’s marina in downtown Portland for two weeks. Are you sensing a theme here? It’s hard to get too much of Portland.

In Old English, Portlanda meant “land surrounding a harbor.” It’s a minor distinction, you might say, but I see Portland as a “harbor surrounding land,” for the harbor met us first and introduced us to the city. Few harbors are as welcoming as Portland’s, which you access by threading your way through the outer islands. It is a pharologist’s dream, with lighthouses appearing on each head of land. From Ram Island and Portland Head, to Spring Point Ledge and Bug Light, Portland’s harbor reveals itself gradually. Portland Head Light and its red-roofed buildings might be one of the most photographed lighthouses in the world.

Entering the inner harbor and Diamond Island Roads allows a close pass by Fort Gorges, an abandoned Civil War era fort which curiously never saw action or even a single soldier, as the fort was obsolete before it was finished. At just two miles from the city docks, the fort is visible from downtown, but is only accessible by dinghy or kayak. Open, but unmanaged and unmaintained, it makes a fascinating destination for adventurous history buffs.

From the downtown docks, local ferries run regular schedules to the islands of Casco Bay, and high-speed ferries depart daily with service to Nova Scotia. Add to this a rainbow collection of kayaks and miscellaneous small boat traffic, and Portland’s harbor becomes a busy place in the summer months. Making your way through on a slow bell and with a watchful eye is the order on deck.

Like all worthwhile destinations, Portland is layered—the best parts take a little effort to discover. Upon landing in Portland, you’re first met with the Old Port neighborhood and the docks surrounding the harbor. From the breweries and upscale eateries ensconced in old warehouses on cobblestone streets, to the working fish houses precipitously hanging over the harbor on their wooden pilings, the waterfront is a healthy mix of old and new. If your visit began and ended here, you would have a wonderful introduction to the city, but you would have only scratched the surface of what Portland has to offer.

Like most of Maine’s coast, the land rises in elevation when leaving the water. In spite of this topography, Portland is quite a walkable city. For a cultural diversion from your days at sea, a healthy walk up and away from the harbor brings you to the city’s Arts District. Portland’s Society of Art is the oldest public art institution in the country, founded in 1882. The neighborhood around the Society of Art is home to the Maine College of Art and Design, the Institute of Contemporary Art and a diverse collection of studios and galleries. If you can time your visit with a first Friday of the month, local artists will invite you into their galleries in the First Friday Art Walk, a popular self-guided tour of the area’s art offerings.

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Portland’s chefs are equally as talented and display their art on your dinner plate. Now rivaling famous food cities like Charleston and New Orleans, Portland is quickly becoming one of the country’s leading foodie destinations. Locavores will appreciate the dedication to regionally sourced ingredients. Fresh seafood from Maine’s abundant waters blends deliciously with local farmers’ harvests. Craft bakers look for local grain harvested and milled near their ovens to produce mouth-watering temptations. If you’re an early riser, you can be first in the very long line that forms at the Standard Baking Company each morning. Just a short walk from the waterfront, this famous bakery is a destination unto itself.

While you’re upland from the harbor, don’t miss taking in the view of Casco Bay from East Promenade Park, Portland’s 62-acre window on the water. The park’s hiking and biking trails lead to some of Maine’s prettiest beaches. A public boat ramp provides easy access for small boat and kayak launching. From the park, it’s an easy paddle out and around Pomroy Rock or even out to Fort Gorges. It’s an ideal spot to get a glimpse of one of the Portland Schooner Company’s graceful historic ships for a perfect Portland postcard picture.

For a unique combination of boating, island exploring and a gastronomical adventure, take your own boat or a Casco ferry to Great Diamond Island for lunch at Diamond’s Edge Restaurant & Marina. As it’s only open in the summer, be sure to make reservations in advance for a table on the lawn. From the scenic trip out to the meal to the setting and the view, you will be well rewarded for the effort.

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In planning this excursion, if you sense you may want to stay on the island for longer than an afternoon, book a room at the four-star Inn at Diamond Cove. Both the inn and restaurant are located in the old 1890’s Fort McKinley. The inn is housed in the fort’s former barracks overlooking the parade ground, with Casco Bay in the distance.

It is true that summer seems short in these latitudes, but in Portland’s case, I think that’s only because there isn’t enough time to take in everything this land surrounded by water has to offer.

This article originally appeared in the August 2022 issue of Power & Motoryacht magazine.

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