The first time I lay eyes on Portland , Maine from the deck of the Nova Star cruise ferry from Yarmouth , it’s obvious this city has a history as a busy port.

Maine’s nouveau chic port city

The first time I lay eyes on Portland , Maine from the deck of the Nova Star cruise ferry from Yarmouth , it’s obvious this city has a history as a busy port. The working waterfront is crammed with fishing boats, tugs, ferries, yachts and a cruise ship, carrying on its legacy as an important harbour. Restaurants, shops, fishmongers and condos balance over the water.

What’s less obvious, until I hit the streets, is just how hip and vibrant Portland is today. Artisans hawk paintings, turned wood and handmade jewellery along busy waterfront sidewalks. A fierce spirit of independence permeates the downtown.

Notable by their absence is any significant infestation of fast food or even fast coffee. In fact, Men’s Health magazine ranks Portland as America’s number one coffee city. After a night’s rest, a stop at one of five Coffee By Design locations in the city confirms that Portland is java hut heaven.

Mocaccino in hand, I step outside to the aroma of fresh bread. Next door is a modest storefront called Two Fat Cats Bakery. Inside, a shelf groans with pies like Bourbon Pecan, Sour Cherry and Mixed Berry. Loaves of bread and other baked goods line the counter. I select a gigantic cinnamon bun to complement my mocaccino. I turn (too late) to read a sign, “Pie for Breakfast: slice of pie & coffee $3.75.”

Portland’s proudly independent baristas are easily matched by its brewers and distillers, of which there are 10 in the peninsular downtown alone. The largest of these is Shipyard , and while the store there is stuffed with both beer and memorabilia and even a line of flavoured sodas, it’s the little guys that make for a unique experience.

I head across town to Maine Craft Distilling and Rising Tide Brewing , side by side micros, for lunchtime samplings. Because the distillery is relatively new, the spirits are young, but they’re on to a good thing with their Alchemy Gin spiced with coriander, cardamom and lemon peel supplementing the usual juniper. Out one door and in the other, I belly up to the sampling bar for tastes of all three Rising Tide mainstays and several seasonal and limited release brews, of which their smooth, caramel malt brown ale, Armada, is the best.

Time for lunch. Back on the waterfront, I find one of the most popular of Portland’s 300-plus restaurants (more per capita than any other American city) some with the feel of landmarks. There’s a lineup at J’s Oyster Bar , a gritty little place hanging over the water. A short wait gets me inside the classic, no-frills seafood shack with tables around a horseshoe bar and, as advertised, a fine selection of oysters including stewed, stuffed, baked and nude.

Too plentiful to discover on my own, I sign up with Maine Foodie Tours to sample Portland’s many flavours. I meet guide and chef Stephanie Brewer at Vervacious , a gourmet shop on the waterfront under the motto, “Travel far, eat well, live long.” She fuels us with samples of Maine blueberry mead before we set off to appreciate other delicious Portland originals.

Of these, the Public Market House is the star. It’s a small artisanal shopping mall fit snugly inside a single storefront on Monument Square, the heart of the hip arts district and site of a twice-weekly farmers market. Maine brags the second highest concentration of cheese makers in America, and many are represented here at K. Horton Specialty Foods. National first prize winner Debbie Hahn sells her cheeses only in local Maine shops like this one.

A chipper and knowledgeable Stephanie Brewer leads us on to hand-dipped chocolate truffles at Dean’s Sweets , a sampling of the “wholesome” treats at The Holy Donut (my favourite is sweet potato ginger) and back at our starting point, Vervacious, for lobster sliders with spicy African harissa mustard. Stephanie leaves us with a sampling of brews at Gritty MacDuff’s , founded in 1988 as Maine’s first microbrewery since the end of prohibition.

As a proper punctuation to a foodie tour of Portland, I make a reservation at Walter’s for dinner that evening. Another Portland landmark, this one of the gourmet variety, Walter’s is known for chef Jeff Buerhaus’ creative menu and expertly paired wines. The starter alone sells me—an elegantly presented, delicately flavoured Ahi Tuna Tartare matched with a glass of straw-yellow, intensely floral Gewürztraminer from the Elena Walch vineyards of northern Italy. One taste of the main of Lobster Gnocchi topped with house-made ricotta and a glowing orange mound of tobikko roe and it’s clear—the lobster revolution is on in Portland.

Back aboard the Nova Star, I watch Portland fade with the setting sun and wonder how it came to feel so familiar so quickly. Then it comes to me. Portland is a near twin of Halifax with which it shares a walkable downtown at harbour’s edge on a small peninsula; at the city’s heart is a vibrant arts scene. Historically, they share a nautical past and each was rebuilt following a major disaster. Portland’s was the great fire on July 4th, 1866, which resulted in citizens rebuilding with the brick and stone that gives the city its historic visual charm today.

As darkness descends, I bid farewell to Halifax’s unofficial sister city and head to my cabin to rest after a jam-packed gourmet tour of Portland.