Portland trip planner

Create a fully customized
day-by-day itinerary for free

Itinerary Planner
+ Add destination
2 adults
Adults
- +
Teens
- +
Kids
- +
Close

Portland

Trip Planner USA  /  Maine  /  Portland

The Forest City

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port. Historic red-brick buildings and cobblestone streets make up much of its bustling Old Port area, where seafood restaurants sit just a stone's throw away from the working wharves. Downtown boasts a wide array of stores, bars, world-class museums, and art galleries. Trendy locals tend to congregate in the Munjoy Hill neighborhood, home to some of the city's hippest cafes and bars. When the sun is shining, locals and visitors enjoy relaxing in the city's ample green spaces. Customize your holiday with our United States road trip app to create an adventure that suits you.
Create a full itinerary — for free!

Plan your trip to Portland

  • Get a personalized plan

    A complete day-by-day itinerary
    based on your preferences
  • Customize it

    Refine your plan. We'll find the
    best routes and schedules
  • Book it

    Choose from the best hotels
    and activities. Up to 50% off
  • Manage it

    Everything in one place.
    Everyone on the same page.

Where to stay in Portland

You'll discover a number of hotels in Portland's waterfront area--one of the city's liveliest neighborhoods--that offer proximity to a selection of restaurants and bars. If bed and breakfasts are more your style, look to the city's West End, where a number of establishments sit alongside fine 19th-century mansions. Those interested in staying in Munjoy Hill can find a number of vacation rentals there.
Live like a local, find unique places to stay
Millions of travel reviews on TripAdvisor

Recently planned trips to Portland

15 days in New England BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, popular & hidden gems PREFERENCES: September, culture, outdoors, relaxing, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 15 days in United States BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, romantic, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: June, culture, outdoors, relaxing, romantic, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 20 days in United States BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular PREFERENCES: June, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular PACE: Medium 22 days in United States BY A USER FROM UNITED KINGDOM April, popular PREFERENCES: April ATTRACTION STYLE: Popular PACE: Medium 5 days in Maine BY A USER FROM UNITED STATES January, hidden gems PREFERENCES: January ATTRACTION STYLE: Hidden gems PACE: Medium 11 days in Portland BY A USER FROM UNITED STATES April, popular PREFERENCES: April ATTRACTION STYLE: Popular PACE: Medium 4 days in Rhode Island & Maine BY A USER FROM UNITED STATES November, relaxing, historic sites, wildlife, fast-paced, hidden gems PREFERENCES: November, relaxing, historic sites, wildlife ATTRACTION STYLE: Hidden gems PACE: Fast-paced 28 days in United States BY A USER FROM UNITED STATES January, culture, relaxing, romantic, historic sites, popular PREFERENCES: January, culture, relaxing, romantic, historic sites ATTRACTION STYLE: Popular PACE: Medium 3 days in Portland BY A USER FROM INDIA January, popular PREFERENCES: January ATTRACTION STYLE: Popular PACE: Medium 2 days in Portland BY A USER FROM UNITED STATES November, slow & easy, popular PREFERENCES: November ATTRACTION STYLE: Popular PACE: Slow & easy 5 days in Portland BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, romantic, beaches, wildlife, popular & hidden gems PREFERENCES: June, culture, outdoors, relaxing, romantic, beaches, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 24 days in United States & Montreal BY A USER FROM UNITED STATES September, popular PREFERENCES: September ATTRACTION STYLE: Popular PACE: Medium
View more plans