Portland, Maine: Coastal Windjammer Sailing Cruise
Glide through the pristine waters of Casco Bay on Bagheera, Wendameen, or Timberwind sailing ships, and experience Maine's historic craftsmanship on this sailing boat ...
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Route: Old Port walking tour featuring Maine classics, cultural and up-and-coming food and beverage stops with historical context
Tip: Open year-round. French-language tours also available. Book via FareHarbor on the operator site.
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Portland: Fish Auction Tour & Cultural Seafood Tasting
Discover Maine’s working waterfront on a guided seafood tour. Learn about aquaculture, sustainability, and the local seafood economy, and enjoy a culturally-inspired s...
Portland: Walking Food Tour – Warm Donuts & History
Experience the famed donuts and history of Portland's Old Port on a guided walking tour with a local guide.
Also in old-port
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.
Casco Bay Schooner Sail ★ 4.3
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.
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.
More food tours in Portland
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.
Casco Bay Schooner Sail ★ 4.3
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.
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.