Recommended Sailing
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Explore one of the prettiest coastal towns on the East Coast on a cruise to Portland, Maine. Perched on a peninsula jutting out into the island-specked Casco Bay under vast skies, the scent of the ocean on the breeze, this enchanting spot is rich in history. Having been a fishing and trading port since 1632, Portland is defined by its impressive lighthouses, not least Portland Head Light.
Downtown, you’ll find an old-fashioned ambiance in the cobblestone lanes, old brick buildings, and 19th-century warehouses, as well as a creative, arty community served by some excellent museums. There are fabulous restaurants, too; on your New England cruise, sampling the sweet lobster for which the city is famed is a must.
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New England is known for its picturesque lighthouses. The Portland Head Light is one of the most famous, having stood on the lonely, rocky peninsula of Fort Williams Park since 1791. Visit the museum in the former Keeper’s Quarters to learn about the history of the light and see displays of navigational aids and old photographs. After your tour, you can hike the coastal trails in the park, taking in magnificent views as waves pound the rocks.
The Portland Observatory Museum is the last remaining maritime signal tower in the U.S. and is a National Historic Landmark. The seven-story tower was built in 1807 on Munjoy Hill. Today, it serves as a museum where you can learn about the evolution of Portland and its role in maritime history. You’ll also enjoy magnificent views down over the city and harbor, as well as Casco Bay, dotted with islands.
The Wadsworth-Longfellow House is famous for being the oldest standing structure on the Portland peninsula as well as being the childhood home of the American poet Henry Wadsworth Longfellow. The house was built in 1785, and its interiors are rich with furniture and art from the 18th and 19th centuries. Join a tour to learn more about Longfellow and the impact he had on the New England political and literary scene.
Founded in 1882, the Portland Museum of Art is the oldest and largest public art institution in Maine. It provides visitors with a look into the regional art culture and aesthetic of Maine in addition to its permanent collection of American, European, Asian, and contemporary pieces. Admire works by Georgia O’Keefe, Vincent Van Gogh, Andy Warhol, and Claude Monet. One of the most famous paintings housed in the museum is Monet’s Water Lilies, painted in 1914 and one of a priceless series.
Join a guided cycle ride along Portland’s beautiful Eastern Promenade Trail, with wonderful views of the beaches and rocky shoreline. You’ll pass Bug Light, the smallest coastal lighthouse in the U.S., and take in views of Casco Bay and Fort Georges. Cycle tours also visit Mackworth Island, encircled by a walking trail that leads through stands of pine and spruce, with tantalizing views of the sea.
The quaint fishing village of Kennebunkport, its streets lined with handsome Victorian mansions, is famed as the summer home of the Bush family. The town also attracts celebrities all summer long who come for the art scene, the quirky shops, the farm-to-table restaurants, and endless, sweeping sandy beaches. Come here on a day trip and, after browsing the downtown area, jump on a boat for a scenic cruise of the wild, rocky shores, with a chance to peek at Walker’s Point, the Bush estate.
Portland, Maine is known for two culinary treats—fresh lobster and craft beer—although the city’s highly-rated food scene extends far beyond these two. As well as beer, you can try locally produced mead and cider, as well as wines from Maine’s own vineyards. You’ll also find classy coffee roasteries, mouth-watering bakeries, and traditional pubs that reflect the town’s strong Irish heritage.
Look out for seafood of all kinds on the menus, like lobster, oysters, delicious chowders, and fresh fish straight from the Atlantic. Farm-to-table produce is abundant here, too. Dine in a waterfront restaurant, or wander the streets and wharves around the Old Port and take your pick. Portland is famed for its food trucks, too, which offer anything from artisan gelato to gourmet donuts.
Portland’s history has long been tied to the sea. The long peninsula on which it’s located was called Machigonne (“Great Neck”) by the Native Americans who first lived here. When the British began building colonies in America, they also found the peninsula to be an alluring piece of land and established it as a trading and fishing settlement in 1632.
Originally called Casco and then Falmouth by the British, the name was changed after the Revolutionary War to Portland. The city continued to grow as a commercial port and shipping center. When Maine became a state in 1820, Portland served as the state’s first capital until 1832, when it was switched to more centrally located Augusta.
Portland has two terminals: the Portland Ocean Terminal (also referred to as the Maine State Pier) and the Ocean Gateway Terminal. The two terminals are located just a few blocks apart adjacent to Commercial Street. Larger cruise ships will dock at the Portland Ocean Terminal.
From the cruise terminals, you’re within walking distance to downtown Portland and all its popular neighborhoods, including the Old Port shopping district and the Arts District. There’s a tourist information center at the terminal and in summer, a free guiding service from Downtown District Guides.
Taxis wait outside the cruise terminal, and rideshare services operate in the city. You can explore beautiful Casco Bay on the local ferry service, Casco Bay Lines; ferries depart from their own terminal, around 15 minutes’ walk from where cruise ships dock.
Portland also has a Metro bus system that operates within the Greater Portland area and has a service to Freeport. You can rent a car downtown. A highly enjoyable way to get around is on two wheels, with bike rentals available close to the port.
The city’s Arts District is full of galleries and antique shops, while the Old Port area has everything from clothing boutiques to homewares. Items to look out for include foodie gifts such as chocolate and spicy sauces, upcycled bags and purses, nautical memorabilia, artisan candles and soaps, ceramics, jewelry, tasteful homeware, and local fashion.
Portland and the rest of Maine use the U.S. dollar, and there are numerous ATMs located around the city. Credit cards are accepted in most places, although you should check when hailing a taxi whether they take cash or card. Tipping is customary in the USA, with 15% to 20% of the total bill or fare being the norm.
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