Things to do over Labor Day weekend in Portland (Updated 2026)
Discover Portland City and Lighthouse Tour
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...
$53
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...
$73
Harbor Lights and Sights Cruise
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...
$56
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...
$44
Portland Tall Ship Cruise on Casco Bay
What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this...
$98.75
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...
$53
Port City Lights Cruise
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...
$38
This 105 minute cruise offers guests a chance to relax and unwind as we make our way around the inner islands and lighthouses of the...
$55
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...
$78
Sunset Sea Kayak Tour on Casco Bay
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...
$59
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,...
$68
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...
$53
Board the Elizabeth Grace to cruise around Portland Harbor while sipping local craft beer. This 1.5-hour harbor cruise will take you out into Casco Bay....
$88
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...
$63
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...
$68
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...
$58
Step back in time to the bustling 18th Century port, where shipbuilding, trade, and whispers of strange occurrences at sea filled the air. Known for...
$28
Discover Portland Maine and the shores of Casco Bay by bicycle! Join us for the 5 lighthouse bicycle tour of Portland, Maine featuring the Maine...
$164
Board the Elizabeth Grace for this exclusive one-of-a-kind experience. Whether you are a local or visiting from away, the stone fortresses built in the early...
$108
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,...
$76
