Destination of the Week: Portland, Maine

May 11, 2012

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Portland seen from the Casco Bay Lines ferry as it crosses the harbor.

As Memorial Day approaches, we started thinking about some good old-fashioned American summer destinations, so for today’s Destination of the Week, we set our sights on Portland, Maine.

Destination of the Week pieces are not meant to be comprehensive guides to destinations since we don’t have the time or funds to visit all these places in person and report back to you. Nor are they endorsements of all the hotels we mention. They are simply roundups of top destinations that we have specifically pinpointed for the opportunity they present to use your miles and points to get to and stay there. As always, we welcome your comments to help enrich the content here, provide opinions and first-hand experiences of these destinations.

Though a small city of around 70,000 people (with about half a million in the surrounding area), Portland combines the best of both a friendly small town and a cosmopolitan destination with great restaurants, museums, parks and festivals. The historic Old Port district on Casco Bay is small enough to be manageable without a car and yet packs in an exciting amount of activities. Here are some of our TPG favorites.

The city’s main drag is Congress Street, home to the Arts District, and nearby you can find the Portland Museum of Art, the Portland Stage Company, the Children’s Museum of Maine and the Salt Institute for Documentary Studies and the fascinating Maine Historical Society and Museum.

Homemade honey for sale on picturesque Peaks Island.

Of course, the city owed its foundation and livelihood to the sea, so no visit here would be complete without a trip on a Casco Bay Lines ferry to one of the islands in the harbor. Peaks Island is a quick, easy ride, and once there, visitors can rent a bicycle and circumnavigate the island on quiet, country lanes, many of which run along the seashore. There’s even a small Civil War museum here, and a very good restaurant at the cozy Inn on Peaks, where you can sample local specialties like New England clam chowder and ale-battered fried haddock.

Speaking of food, Portland has become something of a top-rated foodie mecca thanks to a delicious mix of farm-fresh seasonal fare and talented young chefs who have trained in some of the world’s great kitchens and brought their skills back to Maine. Among our favorites is Bar Lola in the city’s Munjoy Hill neighborhood within view of the 19th-century Portland Observatory tower. The menu here changes practically nightly and is served tasting-menu-style so get ready to try a lot of different dishes. On Middle Street, not far from the Casco Bay Lines terminal i s Duck Fat, where you’ll usually find well-heeled hipsters scarfing paninis and Belgian-cut duck fat fries with truffle ketchup and Thai chili mayo. Skip dessert and instead grab a a whoopee pie or an enormous cookie from Two Fat Cats Bakery just around the corner.  Also on Middle Street, Bresca is one of the city’s most popular Italian eateries.

One of the best places in town for a beer is Novare Res, tucked away off Canal Plaza, which is modeled on an Old World beer garden and serves Maine hallmarks like Allagash White; while for a fancy meal out, Five Fifty-Five is the go-to spot for Portland’s movers and shakers. Cap an evening out at Grace, a cavernous restaurant and lounge in a converted 19th-century Methodist Church.

Lobster mac ‘n cheese at Five Fifty-Five.

Bring back some of the gourmet flavors by stopping in at Vervacious Fancy Foods for gifts like chocolate balsamic vinegar and star anise salt. For neat nonperishable gifts, Mad Girl World is a bohemian little boutique on Commercial Street with idiosyncratic wares like beer cosies made from recycled sweaters, retro ski vests, and all kinds of awesomely odd Maine souvenirs.

Though a delightful destination in and of itself, Portland is also the gateway to Maine’s vacation spots including the coastal towns along scenic Boothbay Harbor (the town of Bath is one of the state’s best antiquing spots), the shores of Moosehead Lake, way up in the north, and, of course, the breathtaking natural beauty of hiking paradise Arcadia National Park (which is actually closer to Bangor, so if this is your prime destination, think about routing through there instead).

The new(ish) terminal building at Portland International Jetport (PWM).

Ask a Mainer where the Portland Airport is and they’ll correct you: it’s the Jetport. The Portland International Jetport, that is. Though small, it’s serviced by Air Canada, AirTran, Delta, JetBlue, United and US Airways, so though you can use your SkyMiles and Star Alliance miles to get here, it looks like Oneworld flyers are out of luck, and any Avios you might have gotten from the current 100,000 bonus won’t do you any good. Still, Portland’s just a 6-hour drive from New York, and under 2 hours from Boston. Or you could turn those Ultimate Rewards points from a Chase Sapphire Preferred or Ink Bold  into Amtrak points and use them to take a train instead. Redemptions start at just 4,000 points for travel within the Northeast zone.


DoubleTree: This Hilton property is actually a bit outside the city near the massive Maine Mall, but it’s a quick drive to both the airport and the city. It has a fitness center, heated indoor pool and whirlpool, all-day dining at the Blue Wave Grill restaurant and lounge, a breakfast buffet, and tons of meeting space. Accommodations include Sweet Dreams Beds by Doubletree, large work desks with ergonomic chairs, complimentary high-speed internet, 32 to 42-inch LCD flatpanel TV’s, and kitchenettes with microwaves and refrigerators. Rates start at $149 a night in May. This is a Category 4 hotel requiring 30,000 HHonors points for a free night.

The Hampton Inn’s lobby.

Hampton Inn Portland Downtown-Waterfront: Another good option for HHonors members, this mid-size hotel of 122 rooms is situation right near the waterfront and the Casco Bay Ferry Terminal. Accommodations include either one king or two queen beds in the rooms, or suites with a separate living area and sofa bed. Guest rooms all have 42-inch color TVs, free high-speed internet, work desks, small sitting areas and bathrooms with shower-tub combos and separate dressing areas. Rates include complimentary hot breakfast, though there’s no full-service onsite restaurant. Rates start at $199 in May. This is a Category 5 hotel requiring 35,000 points.

A water view queen deluxe room at the Hilton Garden Inn.

Hilton Garden Inn Portland Downtown-Waterfront: Also right in the heart of the city’s old Port District on Commercial Street, this Garden Inn offers a complimentary hotel shuttle to and from the airport, free wifi throughout the property, a small fitness center and indoor lap pool and spa tub, a hot buffet breakfast at Great American Grille and full bar service in the Pavilion Lounge. Rooms contain either one king or two double/queen beds, oversize work desks with ergonomic Herman Miller chairs, a small sitting area with armchair and ottoman, 37-inch flatscreen HDTV’s, microwave, fridges and shower-tub combos in the bathroom. Rates in May start at $169. This is a Category 6 property requiring 40,000 points for a free night.

There’s also a Hilton Garden Inn and a Hampton Inn (both Category 4, 30,000 points), as well as an Embassy Suites (Category 5, 35,000 points) near the airport, and a Homewood Suites farther out (also Category 4, 30,000 points).

A studio suite at the Residence Inn.

Residence Inn Portland Waterfront: This all-suite hotel has pretty much the ideal location in Portland’s Old Port waterfront district, just steps from the boutiques and restaurants of Fore Street, as well as to the Casco Bay Ferry Terminal lines that take visitors to the outlying islands. The 179 suites come with king beds and sofa beds and views of either the water or the inner courtyard. Suites also come with separate sitting and work areas, kitchens equipped with full-size refrigerators and cooktops, flatscreen TVs, complimentary internet and daily breakfast. There’s also a small gym, an indoor pool, and meeting spaces. Rates in May start at $199 a night. This is a Category 6 property, so 30,000 points for a free night redemption, or 25,000 PointSavers.

The Residence Inn’s exterior.

There’s also a Marriott and a Courtyard (both Category 5, 25,000 points) near the airport, and a Fairfield Inn (Category 3, 15,000 points) about 3 miles southwest of the airport.

Priority Club
Holiday Inn Portland-By-The-Bay: This hotel is also pretty central, though not quite on the water. It is, however, close to the main drag of Congress Street, and is surrounded by Portland’s Arts District including the Portland Museum of Art and the Civic Center. Rooms look spacious, if a little outdated, though they do come with free high-speed internet access, executive desks and large flatscreen TV’s. The hotel has a small health center, an indoor pool and a business center for guests to work in. The hotel’s restaurant is called Port of Call and serves American fare all day, and also has a cocktail lounge for drinks and small plates. Rates in May start at $125 a night, or 25,000 Priority Club points.

The Holiday Inn’s rather uninspiring lobby.

There’s also a Holiday Inn Express near the airport (20,000 points),  Holiday Inn Express (20,000 points) up in the picturesque town of Freeport (home of LL Bean!) where rates start at $100 in May.

Unfortunately, there are no Starwood properties in the city. However, the chain has plans to open the Westin Portland City Center by March 2014, so SPG members will eventually have an option.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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