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The Road Less Traveled: Summer Cruising In Vacationland - PassageMaker

The Road Less Traveled: Summer Cruising In Vacationland

I’m a former resident of Newport and will always have a tight bond with the town ... err, well, except during the summer when the streets overflow with steroid-fueled meatheads, every decent restaurant is packed shoulder to shoulder, and 120 decibels is the normal level of conversation. Great for commerce; bad for folks looking for less confrontation and more peace. Solution: Head north to Portland, Maine until the summer crowds subside.
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I’m a former resident of Newport and will always have a tight bond with the town ... err, well, except during the summer when the streets overflow with steroid-fueled meatheads, every decent restaurant is packed shoulder to shoulder, and 120 decibels is the normal level of conversation. Great for commerce; bad for folks looking for less confrontation and more peace. Lucky for you (and me) there is a solution: Head north to Portland, Maine until the summer crowds subside.

Why I Like It:
Part of Portland’s charm is that like Newport 40 years ago, Maine’s pearl by the sea remains an active working waterfront with a container port and busy ferry system, along with commercial fishermen and lobstermen. The smell of salt, seafood, and fine dining enveloping the area is intoxicating.

Eat + Drink

There’s no doubt about it— Portland is a foodie town. Yet, long before menus were dominated by a 200-word treatise to describe a fricken green salad, there was J’s Oyster (207-772-4828) on the Portland Pier. When to Go: Anytime you want to while away an afternoon—hopefully it’s raining to assuage the guilt—sucking down fresh oysters and enjoying homemade chowder. Vibe: Colorful local patrons mix with Ray Ban- and tight-jean-wearing hipsters, who upon entry immediately realize this is not the establishment to ask for the organic cocktail list. Yet it all works. Central Provisions (www.central-provisions.com) is the latest must-go-to restaurant in Portland. Believe the hype. The small-plate presentation is over the top. When to Go: It’s walk-ins only and not too big. So we suggest an early lunch versus dinner, and get a seat at the bar to watch the chefs in action. Vibe: New York and LA quality, drowned in Maine sensibility, means world-class food and service without the patina of bullshit. The Porthole Restaurant & Pub (www.portholemaine.com) is tucked into the Custom House Wharf. When to Go: It’s my pick for breakfast. What to Have: Hey you’re in Maine. Think about going all in with the Casco Bay Omelet filled with lobster, crab, goat cheese, and tomatoes. Vibe: If you’re lucky enough to get an outside table, I promise you’ll sit back, smile, and fall hard into the vacation zone. Just don’t feed the seagulls. No, seriously, don’t feed the seagulls.

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Shops + Treats

For all those naysayers who fuel the narrative that independent bookstores have gone the way of the telephone booth, head on up Exchange Street and savor Sherman’s Books & Stationery. It’s a must stop before heading Down East where a good book is as essential as radar. Afterwards, walk over to Portland Trading Co. (www.portlandtradingco.com) on Middle Street. The store is simply a wonderful, elegantly curated collection of home goods, clothing, accessories, and books.

Water + Cruising

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For the full Portland experience it’s tough to beat Dimillo’s Marina (www.dimillosmarina.com) in the heart of the Old Port. From Portland, head out to Casco Bay for the day and enjoy the many islands dripping with beauty and serenity. Take a slip at Diamond Cove on Great Diamond Island (www.diamondcove.com) and walk up to the Diamond’s Edge restaurant for a cocktail and early dinner on the lawn next to the harbor. The entire development is built around the buildings of the former Ft. McKinley. Admiral Robert E. Peary’s Eagle Island (www.pearyeagleisland.org) is open to the public in the summer for tours. It’s easier to grab a mooring and take your dinghy into the dock.

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