Every bookable experience in Portland, Maine, with the operators we recommend first.
GetYourGuide lists 48 bookable experiences in Portland, Maine, 14 of them about food and drink. 2 of the operators we recommend in our own guides sell there too, and those come first below. Prices start from USD 24, and most listings can be cancelled free up to 24 hours ahead.
For what we actually recommend eating and doing, start with our own guides: food tours in Portland, Maine, cooking classes, markets and day trips worth eating your way through. This page is the bookable layer under them.
These are operators we researched and recommend in our own guides, where the same company sells the same experience on GetYourGuide. Booking there gets you their live calendar and free cancellation on most listings.
Maine Day Ventures (rebranded from Maine Foodie Tours in 2024) runs a 3-hour Old Port culinary walking tour with classic Maine, cultural and up-and-coming.
On GetYourGuide as: Portland: Old Port Seafood Lovers Tour, sold by Maine Day Ventures
On Viator, sold by Maine Day Ventures
Portland Schooner Company runs two-hour Casco Bay sails on the historic 1924 Bagheera and 1925 Wendameen schooners from Maine State Pier (56 Commercial.
On GetYourGuide as: Portland, Maine: Coastal Windjammer Sailing Cruise, sold by Portland Schooner Co.
On Viator, sold by Portland Schooner Co.
Tastings, food walks, cooking classes and dinners on the marketplace, ranked the way GetYourGuide ranks them.
Glide through the Casco Bay waters on Ruth, the 39' long classic, picnic-style boat to view the Portland Head Light, Bug Light Park, Spring Point Ledge Lighthouse, and...
Discover Maine’s working waterfront on a guided seafood tour. Learn about aquaculture, sustainability, and the local seafood economy, and enjoy a culturally-inspired s...
Portland, Maine’s harbor is packed with treasures waiting to be discovered. Aboard the Elizabeth Grace, with local craft beers in hand, enjoy a stunning journey throug...
Experience the famed donuts and history of Portland's Old Port on a guided walking tour with a local guide.
Eat your way through one of Maine's most "foodie" centric cities on this culinary walking tour of Portland. Enjoy a leisurely walking tour that carves a path through t...
Explore southern Maine on a relaxed day trip from Boston, featuring the Marginal Way, Kennebunkport, Portland’s Old Port, and Portland Head Light—packed with coastal v...
Join the #1 ghost tour in Portland, Maine—operating nightly, year-round! Explore haunted stops like Andy’s Old Port Pub & Portland Harbor Hotel. Hear chilling tales of...
Discover the haunted history of the Old Port neighborhood in Portland on a guided ghost tour. Learn about the maritime mysteries of the historic waterfront and local a...
Enjoy a private pickup from Portland International Airport and discover the city on a 2-hour tour. Visit the International Rose Test Garden, see Washington Park, and g...
Cruise along Corfu’s northeast coast. Swim in crystal-clear waters, discover hidden bays, and enjoy a freshly prepared BBQ meal onboard.
With a small group, trace the steps of Black explorers, mariners, religious leaders, and politicians, over 400 years of Maine history. Follow a public historian throug...
Dive deep into the local brewing scene on this tasting tour to three local breweries in and around Portland, Maine. Choose from a variety of unique tour options to sui...
The Portland Pub Walk is a leisurely 3-stop, 1 mile stroll through Portland’s Old Port. This is a journey through Maine's unique history with Portland's finest beer in hand.
Trips out of the city with transport included. Our own day-trips page covers the towns worth eating in; these are the coaches and drivers that get you there.
See coastal Maine on a two-day trip from Boston featuring Portland Head Light, Acadia National Park’s cliffs and beaches, Cadillac Mountain views, and free time in the...
Explore the Columbia River Gorge from Portland on a 4-hour small-group tour for up to 6. Visit Vista House and three waterfalls with an English- or Mandarin-speaking guide.
Walking, bike and themed tours of the city itself.
Jump aboard a trolley to join a fully-narrated sightseeing tour of Portland's diverse historic and hidden gems accompanied by engaging and informative guides.
Discover the maritime history of Portland on a trolley tour. Visit 3 lighthouses and learn about their unique construction. Explore the Bug Light Park and the Liberty ...
Discover the fascinating City of Ships on the Kennebec River. Explore Bath’s stunning downtown Historic District & learn about the people & events of the past 400+ yea...
Our neighborhood tour offers a peek into the area's history and unique 18th and 19th-century architecture. Embark on a journey through the North, South, West End and e...
Explore Portland's downtown, Old Port, and working waterfront on foot in a small group with a public historian. Hidden histories are revealed about folks and events le...
Start your Maine morning with coastal yoga overlooking Casco Bay, then enjoy a locally made treat from one of Portland’s favorite bakeries, picked up ahead of time so ...
Walk through Portland's exciting old town. This 2-hour guided tour is packed with historic landmarks and commentary from a local history expert.
Join a 50-minute, fully narrated tour of Portland while aboard an open-air fire engine.
As we approach the autumn equinox, join us for an immersive evening at Lily Brook Farm. Optional fire circle to close. August 8, 6:00–8:00pm
The most immersive way to see Historic Portland is on foot. Our walking tour takes you down the cobblestone pathways of our historic city in search of spirits that lin...
Cruises and boat trips.
Sail through the waters of Casco Bay while experiencing Maine's historic craftsmanship (NOTE: This is not a narrated tour, but our crew is happy to answer any question...
Relax on the water in the evening glow with this Casco Bay sunset cruise from Portland. Travel through the Calendar Islands and feel the ocean breeze as you glide by p...
Explore the sights and scenes of Casco Bay on a fully narrated scenic cruise. See major sights like Portland Head Light and Spring Point Ledge Lighthouse as well as lo...
Climb aboard a spacious boat with indoor and outdoor seating and enjoy a fully-narrated cruise in Portland. Discover Casco Bay and see iconic lighthouses, forts, lobst...
Enjoy a scenic sail along rugged coastlines and charming harbors. Choose a shared public cruise or a private charter for a more personalized, relaxing experience on the water.
Experience the magic of a Casco Bay sunset on our Private Extended Sunset Powerboat Cruise. This exclusive 4-hr adventure offers breathtaking views as the sky transfor...
Embark on a narrated cruise to Eastern Egg Rock and see the puffin colony. Spot seals, blue herons, and other wildlife along the way.
Step aboard an amphibious vehicle for a thrilling tour of Portland's top sites, exploring colonial districts and Victorian monuments before splashing into Casco Bay fo...
Soak in the views of Portland, Maine aboard a famous schooner tall ship. Cruise the rugged coastline of Casco Bay and catch sight of seals, lighthouses, and coastal wildlife.
Your own guide, your own pace, priced per group rather than per person on most listings.
⭐ Top-Rated Vacation Photoshoots 2025 Get a set of high-quality photos to remember your trip to Portland. A professional photographer will guide you through and take p...
Dive into Portland's maritime heritage and cultural landmarks on a personalized guided tour, exploring its rich history.
The same city on Viator (Tripadvisor's marketplace), top rated first: a third place to compare dates and prices.
Our 2-Hour tour leaves at 9 am or 3 pm and follows the scenic South Portland Greenbelt Pathway to two local lighthouses. The first stop on the tour will be Portland Br...
Depart with us from bustling Portland Harbor as we tour one of Maine’s most picturesque boating destinations. Casco Bay is littered with islands, historic forts, wildl...
Private Casco Bay Cruise – Up to 5 Guests Experience the beauty of Maine’s coast on a private 2-hour tour through the scenic Casco Bay islands. This intimate charter i...
The Must-Do Sebago Lake Experience! Explore the panoramic views of Sebago Lake with our unbeatable rental package! With our EZ Launch system, you'll enjoy easy access...
Dive straight into Portland’s working waterfront—where the smell of the sea, and the bustle of the wharves, set the tone for an unforgettable walk through the city’s p...
Hop on the “Guardians of the Harbor” trolley tour, a narrated journey with three lighthouse stops. Explore Portland’s maritime history and scenic beauty, disembarking ...
Experience the breathtaking beauty of New England’s White Mountains on this private guided tour from Portland, Maine. This full-day adventure combines spectacular moun...
All our tours take place in a comfortable vehicle with a local driver-guide and can be tailored to your pace. This private tour is done in our larger passenger van tha...
This is a fully private Southern Maine coastal experience designed exclusively for your party (2–5 guests). No bus groups. No shared travelers — just your group, your ...
Discover coastal New England on this private day tour from Portland, Maine to Massachusetts’ North Shore and Cape Ann. This thoughtfully curated experience blends gran...
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 e...
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 i...
Sail with us on a two-hour private charter on Casco Bay in Portland, Maine the perfect way to experience the beauty of the rugged coastline, complete with lighthouses,...
Wind down your Maine day with coastal yoga overlooking Casco Bay, then enjoy a sunset toast by the water as the evening light settles over Portland.
Come rent a Jamis Beach Cruiser or Hybrid bike and cycle along the Maine Coast, by lighthouses, forts, and beaches. Two blocks from Eastern Bicycle trail and Bike Greenway