The 15 best things to do in Portland (2026)

The ranked list

1. 

   1. The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

   Outty Ranking93

   Welcome to my hometown! Hop aboard for an authentic 1 hour and 45 minute historical sightseeing tour of Portland, Maine and 3 lighthouses with an experienced guide who is a real local, born and raised in Portland, Maine. 90+ Club at 93/100, 5.0/5 from 1,671 traveler reviews, 1.8h from $74, free cancellation, an Outty 90+ Club member.

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2. 

   2. Portland, Maine: Hidden Histories Guided Walking Tour

   Outty Ranking93

   Meet Portland and the people—of all backgrounds and identities—whose wit and grit have made Maine's largest city what it is today. Your locally-raised guide will captivate you with extraordinary, exciting, and surprising. 90+ Club at 93/100, 5.0/5 from 637 traveler reviews, 2h from $54, free cancellation, an Outty 90+ Club member.

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3. 

   3. A Walk Through Time Tour in Portland

   Outty Ranking89

   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 Ol. Exceptional at 89/100, 4.9/5 from 521 traveler reviews, 2h from $49, free cancellation.

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4. 

   4. Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour

   Outty Ranking89

   Skip the city and head straight to the coast on this dedicated lighthouse tour of Maine’s best lighthouses. Explore three iconic beacons that have guided sailors for centuries, each offering a chance to delve into their. Exceptional at 89/100, 4.9/5 from 1,022 traveler reviews, 2h from $79, free cancellation.

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5. 

   5. Portland City and Lighthouse Tour

   Outty Ranking86

   The most comprehensive tour of Portland! Hop on board a trolley and relax as we show you around. The tour covers all of our most famous sights on the Portland peninsula. Towards the end of the tour, we make a 20-30 minut. Exceptional at 86/100, 4.8/5 from 1,310 traveler reviews, 1.8h from $61, free cancellation.

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6. 

   6. Portland, Maine: Black History Guided Walking Tour

   Outty Ranking85

   Trace the steps of the Black Portlanders who moved our city, state, and country closer to the ideals of freedom, democracy, opportunity, and equality. Maine’s earliest settlements couldn’t have existed without Black labo. Exceptional at 85/100, 5.0/5 from 167 traveler reviews, 2h from $54, free cancellation.

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7. 

   7. Harbor Lights and Sights Cruise

   Outty Ranking84

   Explore the bustling inner harbor, Diamond Pass, and the main shipping channel to get close up views of civil war era forts and as many as 4 lighthouses that guide mariners into Portland Harbor. Exceptional at 84/100, 4.8/5 from 813 traveler reviews, 1.8h from $61, free cancellation.

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8. 

   8. Vintage Fire Truck Sightseeing Tour of Portland Maine

   Outty Ranking82

   This 50-minute sightseeing tour is a fun and unique way to discover Portland, Maine. Board a Vintage Fire Engine and travel back in time as your knowledgeable guide helps relive Portland’s colorful history from a local’s. Exceptional at 82/100, 4.8/5 from 969 traveler reviews, 0.8h from $45, free cancellation.

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9. 

   9. Old Port Culinary Walking Tour from Portland

   Outty Ranking79

   - Portland's culinary culture is made up of many kinds of artisan food and beverage entrepreneurs from bakers, brewers and chefs to confectioners and more - wherever taste and creativity meet! - We combine a unique combi. Strongly Recommended at 79/100, 4.8/5 from 484 traveler reviews, 3h from $160, free cancellation.

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10. 

    10. Lighthouse Bicycle Tour from South Portland with 4 Lighthouses

    Outty Ranking78

    Our 3-Hour tour leaves at 11:00 am and follows the scenic South Portland Greenbelt Pathway to three local lighthouses. The first stop on the tour will be Portland Breakwater Light, also known as "Bug Light" and then the. Strongly Recommended at 78/100, 4.9/5 from 133 traveler reviews, 3h from $115, free cancellation.

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11. 

    11. Portland Walking Food Tour – Warm Donuts, History & Hidden Gems

    Outty Ranking78

    Portland, Maine is known for its culinary scene, including amazing donuts. With this tour, you'll get to sample from the city's best donut shops, while also learning of Maine's connection to the invention of the donut an. Strongly Recommended at 78/100, 4.8/5 from 234 traveler reviews, 2h from $69, free cancellation.

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12. 

    12. Casco Bay Half-Day Sea Kayak Tour

    Outty Ranking78

    Explore the beautiful islands of Casco Bay in this four-hour sea kayak tour. After a brief lesson on the basics of sea kayaking, you'll set out with a licensed Maine Guide. The small group will island-hop through the bay. Strongly Recommended at 78/100, 4.9/5 from 62 traveler reviews, 4h from $85, free cancellation.

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13. 

    13. Sunset Sea Kayak Tour on Casco Bay

    Outty Ranking78

    The hours just before sunset offer the best time for paddling on the waters of Casco Bay. The sky tends to explode with color and the seas often become glassy and calm. This trip involves a leisurely paddle just far enou. Strongly Recommended at 78/100, 4.8/5 from 130 traveler reviews, 2h from $60, free cancellation.

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14. 

    14. Afternoon Windjammer Cruise Along the Coast of Portland Maine

    Outty Ranking78

    Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds (NOTE: This is NOT a narrat. Strongly Recommended at 78/100, 4.7/5 from 281 traveler reviews, 2h from $69, free cancellation.

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15. 

    15. Port City Lights Cruise

    Outty Ranking78

    A fully narrated 60-minute scenic cruise through busy Casco Bay and its innermost islands to see lighthouses, forts, lobster boats, seals, and seabirds. As many as four lighthouses can be seen including a close up view o. Strongly Recommended at 78/100, 4.8/5 from 323 traveler reviews, 1h from $43, free cancellation.

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