Portland: Old Port Seafood Lovers Tour
Savor a Maine seafood luncheon and learn about Portland’s iconic working waterfront with a knowledgeable local guide.
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Route: Two-hour sail on a wooden schooner around Casco Bay
Tip: Seasonal May through October. Sunset sails fill earliest; book online.
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Casco Bay Mailboat Run ★ 4.0
Casco Bay Lines runs the year-round working mailboat on a 2-hour-45-minute Bay run through Peaks, Little Diamond, Great Diamond, Long, Cliff and Chebeague.
Tip: Year-round operation. Morning and afternoon runs have different island schedules.
Old Port Culinary Walking Tour ★ 4.6
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.
Tip: Open year-round. French-language tours also available. Book via FareHarbor on the operator site.
Old Port Happy Hour Tour ★ 4.2
Maine Day Ventures runs an Old Port Happy Hour tour Mondays and Tuesdays, a cocktail-bar crawl through the working-waterfront blocks with small plates.
Tip: Mondays and Tuesdays only. $99 per person. Book via FareHarbor on the operator site.
Lucky Catch Lobster Boat Tour ★ 4.8
Lucky Catch Cruises runs 80 to 90-minute working lobster-boat tours on Casco Bay from Long Wharf, 170 Commercial Street; haul real traps with the captain.
Tip: Tours run May through October. Portland Lobster Company next door will cook your catch.
Portland Brewery Bus Tour ★ 4.5
The Maine Brew Bus runs 3 to 4-hour bus tours from 111 Commercial Street, hitting 3 to 5 breweries on Industrial Way or East Bayside with samples poured.
Tip: Choose between Industrial Way (Allagash, Foundation, Austin Street) or East Bayside (Bissell, Rising Tide, Oxbow) tours.
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Casco Bay Mailboat Run ★ 4.0
Casco Bay Lines runs the year-round working mailboat on a 2-hour-45-minute Bay run through Peaks, Little Diamond, Great Diamond, Long, Cliff and Chebeague.
Tip: Year-round operation. Morning and afternoon runs have different island schedules.
Old Port Culinary Walking Tour ★ 4.6
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.
Tip: Open year-round. French-language tours also available. Book via FareHarbor on the operator site.
Old Port Happy Hour Tour ★ 4.2
Maine Day Ventures runs an Old Port Happy Hour tour Mondays and Tuesdays, a cocktail-bar crawl through the working-waterfront blocks with small plates.
Tip: Mondays and Tuesdays only. $99 per person. Book via FareHarbor on the operator site.
Lucky Catch Lobster Boat Tour ★ 4.8
Lucky Catch Cruises runs 80 to 90-minute working lobster-boat tours on Casco Bay from Long Wharf, 170 Commercial Street; haul real traps with the captain.
Tip: Tours run May through October. Portland Lobster Company next door will cook your catch.
Portland Brewery Bus Tour ★ 4.5
The Maine Brew Bus runs 3 to 4-hour bus tours from 111 Commercial Street, hitting 3 to 5 breweries on Industrial Way or East Bayside with samples poured.
Tip: Choose between Industrial Way (Allagash, Foundation, Austin Street) or East Bayside (Bissell, Rising Tide, Oxbow) tours.