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Summer Cruising in Maine

Path Less Traveled

When the summer crowds flock to Newport, Rhode Island, Editor-in-Chief George Sass Jr. heads north to Portland, Maine.

Newport RI and Portland ME

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.

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 ( 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 ( 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.

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. ( on Middle Street. The store is simply a wonderful, elegantly curated collection of home goods, clothing, accessories, and books.


Water + Cruising
For the full Portland experience it’s tough to beat Dimillo’s Marina ( 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 ( 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 ( is open to the public in the summer for tours. It’s easier to grab a mooring and take your dinghy into the dock.

This article originally appeared in the July 2015 issue of Power & Motoryacht magazine.