Things to do in Portland
Discover amazing Portland activities and premium in-home experiences.
Portland, a charming gem along the rugged coast of New England, effortlessly marries historic allure with vibrant modernity. Known for its bustling waterfront, artisanal eateries, and dynamic arts scene, this city offers a delightful tapestry of experiences from savoring fresh lobster rolls to exploring cobblestone streets lined with eclectic shops. Whether you're drawn by the salty sea breeze or the warm community vibe, Portland invites you to immerse yourself in its unique blend of culture and coastal charm.
Popular Activities in Portland
Portland Narrated Vintage Fire Engine Tour
Discover Portland's landmarks and history during a lively 50-minute ride aboard an open-air 1971 fire engine.
Portland Land and Sea Adventure
Explore Portland’s historic sights on land and water aboard a narrated amphibious vehicle.
Portland Historic Walking Tour
Uncover 300 years of maritime and cultural heritage with a guided stroll through the Old Port.
Portland Old Port Seafood Lovers Lunch Tour
Savor Maine's freshest lobster, chowder and more on a guided waterfront walking lunch experience.
Casco Bay Sunset Cruise
Watch Maine's colorful sky from a lobster boat while passing lighthouses and Portland's scenic coastline.
Hands-On Lobster Demonstration in Casco Bay
Haul traps with local crew and learn Maine lobster fishing traditions during a 1.5-hour interactive cruise.
Portland Harbor Beer, Wine and Oysters Cruise
Sip local beer and wine and savor fresh Maine oysters during a scenic two-hour harbor cruise.
Fort Gorges Sea Kayak Tour
Paddle Portland Harbor and explore a Civil War–era fort with a knowledgeable guide
Half-Day Casco Bay Sea Kayak Tour
Paddle between scenic islands, spot seals and seabirds, and relax on a beach during this guided Casco Bay adventure.
Half-Day Sail in Saco Bay
Explore Saco Bay and nearby islands on a relaxed four-hour sailing adventure
Private Maine Lobstering & Scenic Cruise
Haul lobster traps and admire Saco Bay scenery on a private 1.5-hour cruise for up to six guests
Sailing and Wood Island Lighthouse Tour
Sail Saco Bay and access Wood Island Lighthouse for an exclusive guided visit.
Sunset Sailing Cruise
Watch the sky glow with vivid colors aboard a limited-capacity sailboat
Private Full-Day Powerboat Cruise From Portland Harbor
Explore Casco Bay’s lighthouses, islands and wildlife on a seven-hour private charter tailored to your interests.
Sebago Lake Historical Kayak Tour
Paddle along Sebago Lake and uncover local history on a guided kayak adventure
Half-Day Kayak, Paddleboard, or Canoe Rental on Sebago Trails
Launch from a private dock and explore Sebago waters for up to four relaxing hours
Panther Run and Sebago Lake Sunset Paddle
Relax with a gentle guided paddle and a vibrant Maine sunset
Floating Sauna Experience on the Kennebunk River
Relax in a wood-fired sauna and cool off with a refreshing Kennebunk River dip.
Full-Day Pontoon and Tritoon Rental in Naples
Enjoy eight hours on the water with a choice of power pontoon boats.
Explore the Charms of Portland
Portland is a vibrant city where cobblestone streets meet modern culinary delights and historic charm. Known for its picturesque waterfront, this coastal gem offers an array of activities that capture both the heart and imagination. Stroll through the Old Port district with its unique boutiques, art galleries, and bustling restaurants serving up fresh seafood straight from Casco Bay. The salty sea air mingles with aromas from artisan bakeries and coffee shops, inviting you to pause and savor each moment.
The city's thriving arts scene makes it a cultural hotspot in New England. Visit the Portland Museum of Art or catch a live performance at one of many theaters scattered throughout downtown. For outdoor enthusiasts, nearby Peaks Island offers biking trails with stunning ocean views just a short ferry ride away. Whether you're kayaking along serene waters or exploring lush parks like Eastern Promenade, nature's beauty is always within reach.
No visit to Portland would be complete without indulging in local flavors at one of its renowned breweries or farm-to-table eateries. Each season brings new experiences—from summer festivals celebrating maritime heritage to winter walks on snow-dusted paths by lighthouses standing sentinel against crashing waves—making every trip unforgettable no matter when you arrive.