Trips home
My trips
Favorites
Help
FAQ
©

Greater Portland & Casco Bay trip planner

Create a fully customized day by day
itinerary for free

Itinerary planner

+ Add destination
—
2 adults
Adults
- +
Teens
- +
Kids
- +
Close
Trip Planner :  USA  /  Maine  /  Greater Portland & Casco Bay

Greater Portland & Casco Bay

4.3
Most visitors remember their trip to Greater Portland & Casco Bay by an enticing blend of scenic coastal towns, historic sites, and impressive foodie scene. Dubbed "America's Foodiest Small Town," Portland remains the regional hub of arts, entertainment, and gourmet dining. Home to a popular road race, Cape Elizabeth draws athletes from all parts of the country. Known for its numerous outlet stores, Freeport invites you to go wild on a shopping spree. Big city lures and modern amenities combined with storied traditions and relaxed small-town vibe is what Greater Portland & Casco Bay generously offers. Add Greater Portland & Casco Bay and other United States destinations to your travel plans using our United States route planner.
Create a full itinerary — for free!

    Plan your trip to Greater Portland & Casco Bay

    • Get a personalized trip
      A full day by day itinerary based on your preferences
    • Customize it
      Refine your trip. We'll find the
      best routes and schedules
    • Manage it
      Everything in one place. Everyone on the same page.
    Know more

    Places to visit in Greater Portland & Casco Bay

    PortlandTrip planner Best for: Beer Tasting / Tour, Brewery, Art Museum FreeportTrip planner Best for: Factory Outlet, State Park, Brewery South PortlandTrip planner Best for: Lighthouse, Fishing Charter / Tour, Park Bailey IslandTrip planner Best for: Hiking Trail, Gift & Specialty Shop, Bridge WindhamTrip planner Best for: Mini Golf, Movie Theater, Bridge

    Visit a single location or make it a multi-destination trip.

    Popular things to do in Greater Portland & Casco Bay

    Portland Head Light ©
    Lighthouse
    Portland Head Light
    Cape Elizabeth
    4.8
    Duration: 2h 30 min
    Allagash Brewing Company ©
    Brewery
    Allagash Brewing Company
    Portland
    4.8
    Duration: 2h 30 min
    ©
    Fishing Charter / Tour
    Fishing Charters & Tours
    Portland
    4.9
    Duration: 2h 30 min
    Eastern Promenade Trail ©
    Biking Trail
    Eastern Promenade Trail
    Portland
    4.7
    Duration: 2h 30 min

    Museums in Greater Portland & Casco Bay

    Victoria Mansion ©
    History Museum
    Victoria Mansion
    Portland
    4.5
    Duration: 2h 30 min
    Portland Museum of Art ©
    Art Museum
    Portland Museum of Art
    Portland
    4.6
    Duration: 2h 30 min
    Maine Narrow Gauge Railroad Company and Museum ©
    Specialty Museum
    Maine Narrow Gauge Railroad Company and Museum
    Portland
    4.2
    Duration: 2h 30 min
    Maine Jewish Museum ©
    Specialty Museum
    Maine Jewish Museum
    Portland
    4.7
    Duration: 2h 30 min

    Breweries & Distilleries in Greater Portland & Casco Bay

    ©
    Beer Tasting / Tour
    Beer Tastings & Tours
    Portland
    4.7
    Duration: 3 hours
    Shipyard Brewing Company ©
    Brewery
    Shipyard Brewing Company
    Portland
    4.1
    Duration: 2h 30 min
    Maine Beer Company ©
    Brewery
    Maine Beer Company
    Freeport
    4.7
    Duration: 2h 30 min
    Fore River Brewing Company ©
    Brewery
    Fore River Brewing Company
    South Portland
    4.9
    Duration: 2h 30 min

    Shopping in Greater Portland & Casco Bay

    L.L. Bean Factory Store ©
    Factory Outlet
    L.L. Bean Factory Store
    Freeport
    4.2
    Duration: 2h 30 min
    Freeport Shopping Outlets
    Factory Outlet
    Freeport Shopping Outlets
    Freeport
    3.6
    Duration: 2h 30 min
    Land's End Gift Shop ©
    Gift & Specialty Shop
    Land's End Gift Shop
    Bailey Island
    4.5
    Duration: 2h 30 min
    Len Libby Chocolates ©
    Gift & Specialty Shop
    Len Libby Chocolates
    Scarborough
    4.5
    Duration: 2h 30 min

    Hidden gems in Greater Portland & Casco Bay

    Bailey Island Bridge ©
    Bridge
    Bailey Island Bridge
    Bailey Island
    4.9
    Duration: 2h 30 min
    Giant's Stairs Trail
    Hiking Trail
    Giant's Stairs Trail
    Bailey Island
    4.8
    Duration: 2h 30 min
    Pine Point Beach
    Beach
    Pine Point Beach
    Scarborough
    4.7
    Duration: 2h 30 min
    Crescent Beach State Park
    Beach
    Crescent Beach State Park
    Cape Elizabeth
    4.1
    Duration: 2h 30 min

    Kid-friendly things to do in Greater Portland & Casco Bay

    Casco Bay ©
    Water Body
    Casco Bay
    Portland
    4.8
    Duration: 2h 30 min
    Children's Museum and Theatre of Maine ©
    Children’s Museum
    Children's Museum and Theatre of Maine
    Portland
    4.3
    Duration: 2h 30 min
    Higgins Beach ©
    Beach
    Higgins Beach
    Scarborough
    4.3
    Duration: 2h 30 min
    Ferry Beach ©
    Beach
    Ferry Beach
    Scarborough
    4.7
    Duration: 2h 30 min

    Featured attractions

    Wicked Walking Tours ©
    Nightlife
    Wicked Walking Tours
    Portland
    4.7
    Duration: 1h 30 min
    Portland Paddle ©
    Multi-day Tour
    Portland Paddle
    Portland
    4.9
    Duration: 3 hours
    Old Port ©
    Neighborhood
    Old Port
    Portland
    4.4
    Duration: 2h 30 min
    Commercial Street ©
    Landmark
    Commercial Street
    Portland
    4.3
    Duration: 2h 30 min

    Don't Miss a Thing.
    See & Do More.

    Recently planned trips to Greater Portland & Casco Bay

    13 days in United States BY A USER FROM UNITED STATES Covington Richmond Washington DC 9 days in United States BY A USER FROM UNITED STATES Washington DC Portland Bar Harbor 23 days in United States BY A USER FROM ITALY Houston New Orleans Washington DC 4 days in Portland & Bar Harbor BY A USER FROM UNITED STATES Portland Bar Harbor 8 days in Greater Boston, Portland & Chatham BY A USER FROM UNITED STATES Boston Portland Chatham 15 days in New England BY A USER FROM UNITED STATES Boston Quechee Burlington
    See all trips