Top Things to Do in Portland

Step aboard a vintage trolley in portland, ride through cobblestone streets, visit victoria mansion, and pause at portland head light. includes narration by a local guide....

Feel portland’s working waterfront, historic lighthouses, and vibrant neighborhoods in a small-group tour led by a true local. includes guide and air-conditioned van....

Feel the sea breeze on a casco bay sunset cruise from portland, with lighthouse views, city lights, and stories from a local guide. includes restroom onboard....

Warm donuts, local tales, and a stroll through portland’s old port. sample six hand-picked donuts, meet bakers, and skip the lines—includes coffee or water....

Feel the salt air on a portland lighthouse tour—walk fort williams park, taste lobster rolls, and hear local stories. includes van transport and guide....

Step onto a vintage fire truck in portland, maine for a lively city tour with local stories, historic sights, and a friendly guide—includes easy check-in on commercial st....

Pedal along south portland’s greenbelt, visit four historic lighthouses, stroll willard beach, and taste local lobster rolls. includes bike rental and local guide....

Feel the salt air on a portland harbor cruise past lighthouses, civil war forts, and casco bay islands. includes onboard bar, snacks, and restroom for easy booking....

Feel the sea breeze cycling portland’s coast, explore 5 lighthouses, and enjoy a giant lobster roll lunch from bite into maine. includes bike, guide, and lunch....

Feel the breeze on a historic windjammer as you sail casco bay from portland, spotting lighthouses & seals. bring your own picnic. two-hour cruise with local crew....

Sail casco bay from portland, maine on a classic windjammer. watch lighthouses, seals, and seabirds drift by. bring your own picnic. includes life jackets for all ages....

Feel the sea breeze on a 60-minute casco bay cruise from portland, spotting four historic lighthouses, forts, seals, and lobster boats. includes bar & local guide....

Hear portland’s untold stories on a walking tour with a local guide. stroll old port, meet unsung heroes, and support the abyssinian meeting house. includes donation....

Start hungry in portland’s old port—taste maine’s creative food scene, hear local stories, and walk with a guide. lunch and sweet treat included....

Follow a local through portland’s old port, taste fresh lobster rolls, chowder, and maine craft beer. seafood lunch tour includes stops at favorite waterfront spots....

Walk portland’s historic streets as local guide dugan shares black history, hidden stories, and real voices. includes donation to abyssinian meeting house....

Step into portland’s old port with a lively walking tour, local stories, and a sweet treat at the end. includes 2-hour stroll, guide, and easy meeting point....

Sail casco bay from portland on a historic maine schooner, spot lighthouses & seals, bring your own picnic or help hoist the sails. two-hour cruise with all ages welcome....

Set out from portland for a private boat tour of casco bay, explore islands, spot wildlife, and see portland head light. includes local guide, drinks, and blankets....