By Teresa Ristow

Pull up a chair on the deck of a weathered wooden pier in Portland, Maine, and listen to the squawks and cries of the thousands of seagulls welcoming you to their historic seaside city. Satisfy your tastebuds with a fresh lobster roll and locally made craft beer while feeling the salty breezes of Casco Bay and the Atlantic Ocean. Watch as the fisherman unload their daily catches at this working waterfront and get ready to explore Portland, a one-of-a-kind city by the sea.

Explore Portland, Maine on the water

Explore Portland, Maine from the water.

The waterfront community of Portland is rich with
sea-to-table cuisine, plentiful breweries and breathtaking views of vast blue waters. While there’s plenty to do in Portland proper, kick off a trip by exploring Casco Bay to revel in scenery, adventure and exercise, and gather great stories to reminisce about while relaxing in town afterward. For the adventurous, Casco Bay and its many islands are best explored by sea kayak, a truly unique experience suitable for even novice kayakers.

The Casco Bay kayaking season is compact, with multi-day kayaking trips typically scheduled for mid-June through mid-September for ideal weather. Booking with an experienced outfitter such as Portland Paddle offers kayakers a planned itinerary with kayaks, meals and other equipment included, as well as the peace of mind of exploring with a guide. Meet at Portland’s East End Beach to pick out kayaks, paddles and PFDs before playing a game of packing Tetris—fitting tents, food and water into the compact nooks and crannies of each tandem sea kayak. After a briefing on paddling techniques, the group’s kayaks take off together from the busy Portland harbor area. Paddle into waters that quickly feel wild and remote—traversing through open ocean and more protected estuaries. Multi-day trips along the Maine Island Trail allow for exploration of the bay at a steady pace with overnight stays at primitive campsites on some of the bay’s many islands. Settle in for a night at the 221-acre, uninhabited Jewell Island. After setting up camp, guides will begin dinner prep while kayakers are free to explore the island, covered in a network of hiking trails with access to secluded beaches. Climb the stairs inside one of the concrete observation towers, once used as military lookouts during World War II, for 360-degree views of the bay. Along the trail, learn about the flora and fauna, which includes towering spruce trees and wildflowers such as violets and rugosa roses, also known as beach roses. Back at camp, enjoy dinner over the campfire and sunset views before heading to bed, falling asleep to the sound of waves lapping against the island shore, resting up before venturing back out on the bay in the morning.

These multi-day excursions require some kayaking experience, so it’s recommended that beginners sign up for a lesson or half-day trip on Casco Bay first to get their sea legs. Try Portland Paddle’s three-hour trip to Fort Gorges, a mid-nineteenth century granite fort surrounded by water just off the shore of Portland.

For those who prefer their adventures remain on firmer ground, experience the bay by taking a short ferry ride from Portland to Peaks Island, one of the many landforms in the bay visible from the Portland shoreline. The island offers a quaint coastline and a small-town feel, and is easily explored on foot, by bicycle or through a guided golf cart tour from Peaks Island Tours. Visit the many shops and restaurants, try one of Lisa’s famous cinnamon buns from Peaks Café and stop by the Umbrella Cover Museum, a quirky destination featuring hundreds of umbrella covers from around the world. Explore all that Portland, Maine has to offer.

In the city

Back in town, set up a home base somewhere in Portland’s vibrant core. Explore all Portland, Maine has to offer. Younger groups will feel at home at the Black Elephant Hostel, a hip centrally located lodging experience. With private and shared rooms, and a communal kitchen, it’s one of the most budget-friendly options in town. For a more traditional hotel experience in the heart of the city, The Press Hotel offers a dose of history in a trendy, modern space. The historic location of the Portland Press Herald has been redeveloped as a boutique hotel with newsy touches, like a letterpress art wall, a two-story vintage typewriter installation and Inkwell, a daytime coffee bar and nighttime drink bar.

After getting settled, it’s time to indulge in the food and drink Portland is known for: lobster and craft beer. You can’t go wrong with a lobster roll from The Highroller Lobster Co., a light and bright diner-style establishment serving up fresh Maine lobster on brioche rolls with more than fifteen sauce options including charred pineapple mayo or lobster ghee.
With more breweries per capita than anywhere in the country (about twenty in a city of 66,000 people) a trip to explore Portland, Maine isn’t complete with enjoying a few good brews. An appropriate stop after a kayaking tour, Rising Tide Brewing Company offers beers including the Chebeague Island (India pale ale), Back Cove (pilsner) and the Main Island Trail Ale. For fermented farmhouse ales, check out Oxbow Blending & Bottling, a beer production facility for Oxbow Brewing Co. (based in Newcastle, fifty miles north). The 10,000-square-foot Portland outpost houses more than 200 oak barrels used for aging and conditioning of fermented “sour” beers and is also a community hub and event space that shares an outdoor patio with Duckfat, a European-style sandwich shop known for its duck fat Belgian fries and milkshakes.

For a bit of cultural exploration, walk the streets of the Portland Arts District, home to several theaters, museums, galleries and schools within a few square blocks of Portland. See art from the past 300 years on display at the Portland Museum of Art, experience the hands-on exhibits at the family-friendly Children’s Museum and Theater of Maine or for something a bit more unusual, visit the International Cryptozoology Museum for exhibits on Bigfoot, yeti, sea monsters and other specimens.

Cap off a trip to the greater Portland area with a visit to the Portland Head Light, the oldest and most visited lighthouse in the country, and arguably the most photographed. It’s located south of Portland in Cape Elizabeth and is adjacent to Fort Williams Park, offering ninety acres of walking trails, picnic areas and gorgeous ocean views. It’s a picturesque end for a memorable trip to Portland.

Explore the other Portland. Plan a trip with AAA:

Download the AAA Mobile app for maps, discounts, restaurants, and lodging at For help planning your trip, find a local AAA Travel Agent or call AAA Travel at 800-529-3222.