Top Portland Outdoor Activities

Discover the beauty of Northwest Casco Bay on a 3-hour morning kayaking tour. No experience is necessary, as you get a crash course before the tour begins and your guide is on hand at all times. Double kayaks are available, if you prefer to paddle tandem. See Brunswick and its native wildlife from a unique vantage point. Then enjoy complimentary snacks and a brief land excursion, before your return.

Discover Portland Maine and the shores of Casco Bay by bicycle! Join us for the 5 lighthouse bicycle tour of Portland, Maine featuring the Maine coast, lighthouses, and Portland’s history. We have made some modifications to the 5 Lighthouse tour in response to COVID-19. We have modified the tour to allow us not to have guests in our vehicles. As a result of this change, guests will begin biking from the Ocean Gateway and return to the Ocean Gateway by bicycle.  Groups will generally see only 4 lighthouses (Bug Light, Spring Point, Portland Head Light and Ram Island Ledge). Lunch will be provided by we will source all food from vendors.

Explore the Portland Peninsula by bike with this guided tour. Start at the Eastern Promenade, making your way along the waterfront bike path until you reach the Back Cove Trail. Your guide takes you to the Old Port to see some of Portland's prettiest old brick buildings, and you learn the significance of local food, history and culture of this area.

Looking for a romantic way to watch the sunset while in Maine? How about chartering a vintage lobster boat and heading out to Casco Bay, where you'll take in great views of the sea and coastline. Your captain and guide will be on board to point out lighthouses and natural feature, and you're welcome to bring food and beverages, even the adult kind, on board.

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.

Charter a vintage lobster boat, dubbed MONHEGAN, and set sail with this two-hour tour into Casco Bay. You'll get great views of the Maine coastline, passing by four lighthouses as you go. This is a great opportunity to take photos of the coastline and waters, while learning about local nautical history from a knowledgeable captain.

Learn the basics of sea kayaking on land before launching at Mere Point in Brunswick for a leisurely 3 hour morning tour of Northwest Casco Bay!  Usually we paddle south to the end of Mere Point for a photo op and then on to visiting an island for a stretch break, snacks, and shoreline exploring. Then we paddle back by another island to our launching point. Sea kayaking is an easy, fun way to sight see from the water.  We often see different kinds of sea gulls, cormorants, black ducks, mallard ducks, eider ducks, great blue herons, snowy egrets, osprey and sometimes bald eagles. If we are lucky, we will see a seal. Paddlers of all ages will love exploring Casco Bay in this protected, scenic, historic area! No experience is needed. Single and double kayaks are used on this guided tour by a Master Maine Guide.

Enjoy a relaxing morning paddleboarding along Portland's Casco Bay. After a brief instruction, set out for a stand-up tour of the area—searching out native wildlife such as great blue herons and osprey as you slowly explore the waters. Learn about the area's fascinating history, from ways Native Americans used the land to how lobsters play a big part in the local economy. This leisurely and informative 2-hour tour includes an on-shore snack break before making your way back to Mere Point.

With our Kayak rental, you can explore the natural beauty of Sebago Lake (on your own) and adjacent streams to spot native birds, fish, turtles, ducks, and the picturesque views of this Maine lake.

Join this fun adventure on Sebago Lake. This two-hour outing will teach you the rudimentary skills of standup paddle boarding before journeying out to Jordan Bay of Sebago Lake. Take in the picturesque views on this Maine Lake while spotting wildlife including turtles, blue herons, ducks, geese and fish, as we explore the bends and turns of a small stream Panther Run and the larger bay of Sebago Lake. This outing requires no previous experience and is a relaxed paced paddle.

Operation City Quest of Portland is a great way to see the city in a fun way! You'll use an app on your phone to submit photos of items you find around the city. For every photo you submit, you'll get points. You'll be able to see your score on the rankings after compared to all who have played across the country. All our Scavenger hunts have a live remote host to help along the way. Come out and explore with us in Portland.

Crazy Dash scavenger hunt of Portland, takes you on an adventurous walk around the city. To play Crazy Dash, you'll use an app to collect points by finding items around the city using an app on your phone. You can also perform challenges to gain points. Check out the rankings in the app when you're done to see your score compared to other teams across the nation. All our Scavenger hunts have a live remote host to help along the way. Come out and explore with us in Portland.

Curious about Portland's history with railroads, fires, wars, famous poets and Hollywood producers? Join us for a Walk Through Time! This tour begins on Commercial Street and continues for 2 hours through the historic Old Port, downtown and waterfront areas, sharing highlights of Portland's history since 1632. Some of the locations we may feature on your tour include; the lobster statue, the home of Henry Wadsworth-Longfellow and his place of worship, the Eastern Cemetery, the Abyssinian Church, the U.S. Customs House and more. ***Tour duration is two "ish" hours, based on guest engagement and pace of the group. Planning on 2.5 hours for arriving early to check-in and make it back to your vehicle post tour is recommended.

Wacky Walks of Portland allows your team to discover the city in a fun and different way. The game instructs you to find a variety of items that can be found in the downtown area. For every item you find, you'll get points. You'll also participate in exciting challenges for points as well. See how your points stack up to others on our app rankings. All our Scavenger hunts have a live remote host to help along the way. Come out and explore with us in Portland.

Food lovers can explore Portland's historic Old Port independently, but to uncover the best places serving traditional local fare, you really need a guide to lead the way. Taste the best that Portland has to offer on this guided foodie walking tour, complete with stops at up to seven different eateries—and enough tastings to replace a meal. Along the way, your guide offers some stories about Portland's food scene, so you can get familiar with the local culinary stalwarts.

Zombie Scavengers of Portland is a great way to see the city in a fun way! You'll use an app on your phone to submit photos of survival items you find around the city. For every photo you submit, you'll get points. You'll be able to see your score on the rankings after compared to all who have played across the country. All our Scavenger hunts have a live remote host to help along the way. Come out and explore with us in Portland.

3Quest Challenge of Portland is a great way to see the city in a fun way! You'll use an app on your phone to submit photos of items you find around the city. For every photo you submit, you'll get points. You'll be able to see your score on the rankings after compared to all who have played across the country. All our Scavenger hunts have a live remote host to help along the way. Come out and explore with us in Portland.

This two-hour tour explores the water carved bends and twists of a meandering stream unveiling local wildlife in a rustic backdrop. This tour will continue on to Jordan Bay of Sebago Lake as you paddle alongside lakeside cottages, boats, and man made canals. Here, you will get a panoramic view of the sun as it sets behind the tall pine tree. Along the way the Registered Maine Guide will share in stories that will make the scene come alive! This outing requires not previous experience, and will be an easy and relaxed paddle.

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.

Take in the famous autumn foliage of New England during a private 2.5-hour sightseeing cruise from Portland. With room for six people, it's an ideal intimate experience for couples, friends, or families. It’s also a great opportunity to photograph the leaves and wildlife from a unique perspective. Learn about the area from your private guide as you cruise at a gentle pace.

This self-guided GPS audio walk brings you through one of the most beautiful vistas in Portland, Maine. It starts with a spectacular overlook of Portland Harbor, Casco Bay and the islands, and continues down by the waterfront to East End Beach. Along the way, you’ll hear stories from a local about what it was like growing up on Munjoy Hill and having access to the Eastern Prom. As you cross the railroad tracks, you’ll hear from the engineers that keep the historic steam engines running. Included are tips on what birds to look out for depending on the time of year. Put on a pair of headphones and start the tour by downloading the app. The audio plays automatically at exactly the right place using your smartphone’s GPS. This self-guided tour is narrated by Dianne Ballon - a sound artist, sound designer and an avid bird watcher. She invites you to discover through sight and sound the Eastern Promenade — a place she returns to in all seasons.

Portland's growing hot spot for new restaurants, distillers, oyster shuckers, brewers, roasters, smokers, bakers and more is on Munjoy Hill, along Washington Ave. and East Bayside! There are new food and beverage spots opening up left and right, and this tour will visit several of the bright new stars while highlighting all the culinary pioneers in this newly revitalized area for wining and dining. This tour starts atop scenic Munjoy Hill with the "butteriest croissants", just singled out as a contributor to Portland earning the "Restaurant City of the Year" by Bon Appetite (August, 2018) Then it's a walk past the historic Portland Observatory and Eastern Cemetery with a history lesson in route. The moveable feast continues on Washington and MAY include some of the following: from Triple D famous fried clams, smoked meats, seafood chowder, freshly shucked oysters, frites cooked in duck fat, the "real" Italian & craft beer.

Wend your way through the West End of Portland, an often overlooked section of town, deep in history.