Top Portland Outdoor Activities

Few things are more beautiful than a majestic sunset. However to see it from the waters of Portland's magnificent Casco Bay is a truly remarkable experience. Whether a first-time kayaker or experienced hand, this 2-hour tour offers phenomenal vistas of Portland harbor and cityscsape. Your only neighbors are your guide, your small group and the wildlife as you leisurely paddle back to shore.

Experience the scenic coastline of Casco Bay in Portland, aboard a traditional Maine windjammer. Sail past lighthouses, rocky islands, and wildlife while enjoying the peaceful pace of a classic schooner cruise. Bring your own picnic and drinks to enjoy on board as you take in the views. Suitable for all ages, this relaxing sailing experience offers an authentic way to discover the beauty of the coast.

Set sail for some incredible sights off the coast of Portland, Maine. Keep your eyes peeled for local wildlife, and feel free to pick your captain and crew’s brains on the scenery. Kick back, relax, and bring your own snacks and drinks to enjoy as your captain sails towards wonderful views of lighthouses and historic forts.

Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This is NOT a narrated tour, but our crew is happy to answer any questions you have about the sites). All ages are welcome, whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. See Fort Gorges, Bug Light Park, and the beautiful Portland coastline. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.

Embark on an unforgettable 1.5-hour cruise along Maine's breathtaking coastline at sunset. See four of Maine's most iconic lighthouses, spot seals and seabirds, and take in the historic forts that dot the landscape. Bring your favorite wine or beer and a delicious meal, and unwind as we cruise through the serene waters of Casco Bay. Journey aboard Ruth—a charming 39-foot classic picnic-style tour boat crafted in 1935 at Handy Boat in Falmouth, Maine. Don't miss out on this unique sunset experience!

Experience the breathtaking beauty of the Atlantic Ocean on our whale-watching tour departing from Portland, Maine. Set sail from the historic harbor, where you'll board a comfortable vessel equipped for a thrilling marine adventure. As we cruise along the rugged coastline, keep your eyes peeled for the majestic giants of the sea – humpback whales, fin whales, and minke whales are frequently spotted in these waters. Our experienced naturalist guides will be with you every step of the way, providing fascinating insights into the behavior and biology of these incredible creatures. The tour also offers the opportunity to observe a variety of other marine life, including seals, porpoises, and a wide range of seabirds. Don't forget to bring your camera, as you'll want to capture these unforgettable moments.

Join us for 1 1/2 hours as we cruise along the rugged coastline, complete with lighthouses, seals, seabirds, and historic forts. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the tranquil waters of Casco Bay. All ages are welcome! Whether you are nine years old or 99, cruising aboard Ruth is a unique adventure, a 39’ long classic, picnic style tour boat built in 1935 at Handy Boat in Falmouth, Maine.

Lighthouses are an iconic image associated with coastal Maine and Portland showcases some from the 1800s. Join this bicycling tour in Portland and see two of the city’s lighthouses from the 19th century. Follow quiet roads along South Portland’s coast to reach a small lighthouse called Bug Light, still in use today. Ride farther to Spring Point where a larger lighthouse awaits at the end of a long granite breakwater.

Discover the lighthouses and coastal landmarks of Portland on a small-group biking tour. Hop on a provided bicycle and follow your guide to the Bug Light, Spring Point Ledge, and Portland Head lighthouses. Along the way, learn about their storied histories. Other highlights include the Liberty Ship Memorial, Cape Elizabeth, and Willard Beach. Set at a leisurely pace, the adventure also includes a complimentary lobster roll lunch at an award-winning food truck.

Board your boat, the Elizabeth Grace, near the Portland ferry terminal and cruise around Portland Harbor at sunset, when Casco Bay and the coast of southern Maine are the most romantic. See lighthouses, historic forts, and stray groups of swimming seals and enjoy local craft beer from the boat. As the sun sets, turn toward Portland to see the town light up before returning to harbor.

Explore the lighthouses of the South Portland Greenbelt Pathway by bicycle with this guided tour. You'll visit Bug Light, Point Ledge Light, and Portland Head Light with a local guide. You'll also have the chance to stop at a local food truck for a lunch of lobster rolls before returning to your starting point.

Visit Portland’s scenic coast, historic sites and most vibrant neighborhoods with a sightseeing and shopping tour on a classic fire engine. Get great views of picture-perfect lighthouses and architecture from high up on the engine, and listen to live narration as you tour the city. Learn about Portland’s maritime past as you explore cobblestone streets with enjoy plenty of time to browse souvenir shops and sample the area’s most distinctive foods. Finish your tour in the heart of downtown, near historic wharves, restaurants and boutiques.

Explore the heart of Portland and head out to see some of the area's hidden gems and less-visited spots with this guided sightseeing tour. Your guide, a born-and-raised Portlander who works as a college librarian by day, shows you off-the-beaten-path locations and shares with you all sorts of local lore along the way.

Visitors to Portland can easily miss some of Maine's most stunning sights, since you really need a car to explore the scenic coastline. Avoid the headache of arranging your own transportation or renting a car on this small-group guided tour of Portland's must-see sights. Stop in downtown Portland and visit three lighthouses, including Portland Head Light—an historic lighthouse perched on the rocky coast.

Learn about Portland's history with this walking tour, which will take you through the Old Port, downtown, and waterfront areas. You'll see all sorts of historic attractions, including the home of Hendry Wadsworth-Longfellow, the Eastern Cemetery, and the Abyssinian Church, all with a professional guide on hand to share stories about the city's past.

Explore the Portland Peninsula by bike with this small-group 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 the City of Portland's prettiest old brick buildings, and you learn the significance of local food, history, and culture of this area.

There are a lot of ways to get out on the water in Maine, but we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and comfortable from the moment you step aboard. A half-day sail is the easiest way to get out on the water and see the Maine coast from a completely different perspective. This small group Maine sailing charter is perfect if you want a relaxed few hours to cruise, take in the views, brush up and your sail trim, or just relax and maybe sneak in a swim on a warm day.

This is more than just a yoga class, it’s a sensory coastal experience. Set against the backdrop of Casco Bay, you’ll move through an all-levels flow while breathing in salt air, feeling the ocean breeze on your skin, and taking in the quiet rhythm of the water. Each session is thoughtfully designed to blend mindful movement, nervous system support, and deep relaxation. We’ll move through gentle, grounding flow and close with savasana, including an optional cooling lavender-soaked towel. An invitation to slow down, feel into your body, and experience the coast of Maine in a more present, connected way.

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.

As we cruise the waters around Portland Harbor we will make stops at Portland Breakwater Light, Spring Point Light and Ram Island Ledge Light before stopping at Maine’s oldest and most iconic lighthouse, Portland Headlight. This historic beacon, with its striking architecture and stark coastal backdrop, is a sight to behold from the perspective of the Atlantic Ocean as seafarers have done for more than 200 years. After photos and information about this iconic lighthouse, we continue the ride along the rocky shores of Cape Elizabeth to Two Lights State Park, whose twin lighthouses perch atop dramatic cliffs. Our best chance for wildlife comes during the next leg of the ride as we cruise open waters to Halfway Rock Lighthouse, a true maritime relic. Standing proudly on a remote ledge in the open ocean, it has guided mariners through thick fog and turbulent waters for over a century. Seals are often found hanging on the rocks and feeding in the nutrient-rich waters.

Explore the stunning scenery and rich maritime history of Casco Bay on a private 2hr, 4hr or 6hr powerboat cruise. Ideal for families, friends, or small groups, this exclusive charter offers a personal adventure, allowing you to encounter marine wildlife, view iconic lighthouses, and discover unique islands at your own pace. With flexible scheduling and customizable experiences, this cruise promises an unforgettable day on the water, complete with opportunities for swimming and exploring Maine’s rugged coastline. - Private cruise for up to 6 passengers, ensuring an exclusive experience - Encounter marine wildlife like seals, porpoises, and seabirds - View famous lighthouses including Portland Head Light and Bug Light - Flexible departure times and customizable itineraries available – Alternative pickup available in Portland for added cost, saves 30 min of driving, contact us for availability

Experience the breathtaking beauty of New England’s White Mountains on this private guided tour from Portland, Maine. This full-day adventure combines spectacular mountain scenery, historic rail travel, charming villages, and iconic landmarks that showcase New Hampshire’s famous mountain region. The highlight of the tour is the Mount Washington Cog Railway, where guests board the historic train and travel to the summit of Mount Washington, the highest peak in the northeastern United States. At the summit, guests can enjoy panoramic views, explore the observation area, and visit the small museum. The tour also includes scenic drives along portions of the famous Kancamagus Highway, widely considered one of the most beautiful mountain drives in the country. Along the way we visit picturesque villages such as Jackson and North Conway, see the historic Mount Washington Hotel, and stop at scenic overlooks and waterfalls that make the White Mountains unforgettable.

Come sailing aboard Heart's Desire, designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire is 100 years old this year and has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, Massachusetts, and Maine. This two-hour private, morning sail is the perfect way to experience Maine's coastline. Whether you are interested in getting married in an intimate setting, a special way to celebrate a reunion, birthday or anniversary, or just want to enjoy sailing at its finest, step aboard and plan an event never to be forgotten!