Things to do in Portland, Maine (ME): The Best Outdoor Activities

Half-day bicycle tours of Portland, Maine featuring five lighthouses, Bike and Brews Tour and Bike and hike tour. Also offering multi-day tours in Maine, Canada, Italy, and Macedonia

Lucky Catch Cruises offers 1 1/2 hour lobstering excursions in Casco Bay, Maine. The tours depart from Long Wharf in Portland and operate from the first weekend of May through the last weekend of October. A typical lobster excursion involves pulling eight traps near scenery such as the Portland Headlight Lighthouse, Civil War Fort Gorges and the Seal Rocks. Lobsters can be purchased after the tour for a discounted price and brought to the restaurant next door for cooking. We limit the number of passengers on each boat, so please call ahead for reservations. All the best from Maine!

Deep Sea Fishing Trips, Harbor Cruises, Island Adventures and more with Captain Ed Snell. Family fishing fun!

Wine and food pairing education at its best! You'll be joining with Sommelier Erica Archer for our highly-rated Wine & Food Walks and Wine Sails in Portland, Maine. Wine & Food Walks A guided wine tasting and walking tour of Portland, Maine's vibrant restaurant scene as you explore some delicious examples of wines from around the world paired with delicious foods at four great establishments. Wine Sails Board the immaculate Frances, a 74' Windjammer built by her Captain and crew on the Portland Waterfront, with glasses of fine-wine in hand. Sailing ... sipping ... and swooning over the beauty well crafted wines and Maine lighthouses, waterways, islands and sunsets ... all while indulging in a wine class. Book early. These highly-rated events sell out quickly.

Portland Paddle offers sea kayak and stand-up paddleboard (SUP) rentals, tours and lessons. We provide paddling adventures for all skill levels, including complete beginners. We send out two-hour sunset kayak tours every evening and half-day kayak tours three mornings each week. Experienced paddlers can rent kayaks or SUPs and explore the Maine Island Trail. We're located at the East End Beach a short drive or walk from downtown Portland. Our site on the waterfront of Casco Bay is perfectly situated for paddling. Dozens of interesting islands are nearby and the waters near the beach are relatively calm and protected. We are a seasonal business open from mid-May to mid-October. Our hours may vary in the spring and fall.

Casco Bay Custom Charters is Portland, Maine's, most exclusive boat tour operator. We are the only private charter operator on Casco Bay that uses a vintage wooden lobster boat, and we are the only company to include a tour guide on EVERY charter. Bring your friends, family, or just that special someone and join us in viewing southern Maine's best coastal sights in the relaxed comfort that only a private charter can provide. Whether you want a 2-hour sightseeing or sunset cruise, an evening-long private dinner cruise with our onboard chef, or a half- or full-day adventure around the bay, your family or small group will get an authentic Maine experience that most people only dream of.

We offer family-oriented tours and fishing/lobstering outings on beautiful Casco Bay, Maine. Our most common "Adventure" offers lighthouses, fishing for mackerel, hauling lobster traps and sightseeing forts, seals, eagles and porpoises.

Take a journey back in time and explore beautiful Casco Bay on the Schooner Glory, a half-scale replica of the colonial packet boats that once sailed Portland’s waters back in the 1760’s. Offering 2-hour afternoon and sunset sails out of nearby Spring Point. Come ready to swashbuckle or just kick back and watch it all unfold. Bring a meal and/or your favorite beverage and prepare for adventure on the high seas!

Maine BayCycle is New England's first and only human powered tour boat. Bring your friends and your favorite local brews for a 90 minute cruise of the Portland waterfront. Featuring ten pedal stations and seating for four more, Maine BayCycle is a great way to enjoy Casco Bay. Whether you're hosting a birthday, planning a bachelorette party, looking for a team building activity or would just like to get out on the ocean, Maine BayCycle can fit your needs. Tours must be booked in advance and are offered at 11:00, 1:00, 3:00, 5:00 and 7:00 from Bell Buoy Park, located next to Flatbread Pizza at 72 Commercial Street, Portland, Maine.