Lobster rolls, craft beer, and ocean air
Portland, Maine is a tiny city with one of the best per-capita food and drink scenes in the country. The Old Port's cobblestone streets are packed with craft breweries, oyster bars, and cocktail lounges, while the waterfront delivers lobster bakes and sunset cruises. It's the ideal chill-but-classy party weekend.
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
distillery tour • 1.5 hours
Craft spirits tasting and tour on Washington Ave
boat cruise • 2 hours
Private sailboat charter around Casco Bay islands
escape room • 1 hour
Themed escape rooms in the Old Port with challenging puzzles
tour • 4-5 hours
20-minute ferry to a scenic island with beaches, bikes, and a WWII fort
poker night • 3-4 hours
Cards, chips, and whiskey at the rental — tournament-style with buy-ins
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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