3 hours$75 to $95old-port
Route: Old Port walking tour featuring Maine classics, cultural and up-and-coming food and beverage stops with historical context
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 stops plus a history layer.
2.5 hours$99old-port
Route: Old Port happy-hour crawl through cocktail bars and small plates
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 and drinks at each stop.
80 to 90 minutes$45 to $55 adultold-port
Route: Casco Bay working lobster tour, haul real traps with the captain
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, then have Portland Lobster Company cook the catch.
3 to 4 hours$60 to $85old-port
Route: Bus-based tour of 3 to 5 Portland breweries with sampling
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 at each stop. Tickets $60 to $85.
2 hours$55 to $75old-port
Route: Two-hour sail on a wooden schooner around Casco Bay
Portland Schooner Company runs two-hour Casco Bay sails on the historic 1924 Bagheera and 1925 Wendameen schooners from Maine State Pier (56 Commercial Street), May to October, $55 to $75 a head.
2 hours 45 minutes$25 to $35old-port
Route: Island-hopping working mailboat through Casco Bay islands
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 islands. Tickets $25 to $35 from the Commercial Street terminal.