Casco Bay Mailboat Run is a food tour in Old Port, Portland.
Editorially verified June 5, 2026 by Lewis Vaughan, TableJourney editor. Source.
Route: Island-hopping working mailboat through Casco Bay islands
Tip: Year-round operation. Morning and afternoon runs have different island schedules.
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.
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 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.
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.
Portland Schooner Company runs two-hour Casco Bay sails on the historic 1924 Bagheera and 1925 Wendameen schooners from Maine State Pier (56 Commercial.
Tip: Seasonal May through October. Sunset sails fill earliest; book online.
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.
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 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.
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.
Portland Schooner Company runs two-hour Casco Bay sails on the historic 1924 Bagheera and 1925 Wendameen schooners from Maine State Pier (56 Commercial.
Tip: Seasonal May through October. Sunset sails fill earliest; book online.