Lobster rolls, craft beer, and ocean air
Eventide for the brown-butter lobster roll, Duckfat for poutine and a Sebago between rounds, oysters at the Shop on Washington Ave, dinner at Fore Street with the wood-fired hearth turned up. Charter out of DiMillo's for stripers in Casco Bay, then nightcaps at Hunt + Alpine. Walkable peninsula, ferries to Peaks if the group needs a reset, and Allagash White on every tap.
brewery tour • 3 hours
Guided tour of 3 craft breweries including Allagash and Bissell Brothers
sunset cruise • 2 hours
BYOB sunset sail through Casco Bay's Calendar Islands
food tour • 2.5 hours
Walking food tour through Old Port with 7+ tastings including lobster
boat cruise • 1.5 hours
Haul lobster traps with a real lobsterman on Casco Bay
beer garden • chill • $$
500+ beer list in a cozy Old Port cellar with courtyard
cocktail bar • chill • $$$
Craft cocktails with house-made bitters and syrups on Middle Street
cocktail bar • balanced • $$$
Award-winning cocktail bar with Scandinavian-inspired food
bar • unhinged • $
Legendary dive bar and live music venue on Congress Street
bar • balanced • $$
Craft cocktails and oysters on the corner of the Old Port
bar • balanced • $$
Authentic Irish pub on Commercial Street with live music
speakeasy • chill • $$$
Underground speakeasy on Portland Street with nautical theme
rooftop • chill • $$$
Westin Portland rooftop bar with harbor and island views
Dress code: Smart casual
comedy club • balanced • $$
Maine's longest-running comedy club with national acts and bachelor party packages
dive bar • unhinged • $
Legendary Old Port dive with live punk and rock shows, cheap drinks, and a pool table
Seafood • $$$ • Best for: dinner
Nationally acclaimed oyster bar with the famous brown butter lobster roll
New American • $$$$ • Best for: group-dinner
Wood-fired cooking pioneer and Portland's most celebrated restaurant
American • $$ • Best for: brunch
Duck fat fries, paninis, and milkshakes in a tiny Middle Street spot
Bakery • $ • Best for: brunch
Potato-based donuts in wild flavors -- a Portland morning tradition
Seafood • $$$ • Best for: group-dinner
Waterfront restaurant in a converted marine supply building
Seafood • $$ • Best for: late-night
Cash-only waterfront dive with the freshest oysters in town
Small Plates • $$$ • Best for: group-dinner
James Beard-nominated small plates and raw bar in the Old Port
American • $ • Best for: brunch
Waterfront diner serving fishermen and tourists since 1991
boutique-hotel • Max 2 guests
Converted newspaper building in the Arts District with literary charm
boutique-hotel • Max 2 guests
Historic Congress Street boutique hotel with cocktail bar
airbnb • Max 8 guests
Walk to every bar and restaurant from cobblestone streets
hotel • Max 2 guests
Historic Congress Square hotel with Top of the East rooftop bar
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