Portland, Maine, is a picturesque coastal city known for its charming blend of historic character and contemporary vibrancy. Set along the scenic shores of Casco Bay, Portland is celebrated for its lively waterfront, renowned seafood, and picturesque old port district, where cobblestone streets are lined with boutique shops, art galleries, and acclaimed restaurants. The city’s rich maritime history is reflected in its iconic Portland Head Light and the bustling Portland Harbor, while its cultural scene thrives with numerous festivals, theaters, and music venues. With its stunning natural beauty, thriving local economy, and a strong sense of community, Portland offers a quintessential New England experience brimming with character and charm.
If you're a local and looking to escape for a weekend, keep reading. With a vast array of short domestic destinations, there are also some international destinations within reach. Here are some weekend getaway ideas for locals in the Portland, Maine area within a non-stop 4-hour flight. More importantly, these trips are all possible without having to request PTO (for you M-F 9-5'ers), it just depends on what you want to do at your destination.
New York, New York (JFK, LGA, EWR, ISP, HPN) - 1 Hour 20 Minute Flight
Why go?
It might not be the same city it was before, but it'll always make for a great weekend getaway.
What to do?
Click here to view The BEST Things to Do in New York
When to go?
Summer for the best weather, but you’ll pay peak rates for solid hotels.
Winter for Christmas festivities!
Who can fly you there?
AA from PWM - See flight deals
Delta from PWM - See flight deals
United from PWM - See flight deals
Spirit Airways from PWM - See flight deals
JetBlue from PWM - See flight deals
Southwest from PWM - See flight deals
How much will it cost to get there?
Airfare: $50+
Where can you stay?
Who will pick you up?
Washington, DC (IAD, DCA, BWI) - 1 Hour 50 Minute Flight
Why go?
Museums, walking tours, great mass-transit and cherry blossoms. Fly to DCA for convenience.
What to do?
Click here to view The BEST Things to Do in Washington DC
When to go?
Year-round (spring season for cherry blossoms)
Who can fly you there?
Southwest from PWM - See flight deals
AA from PWM - See flight deals
Allegiant from PWM - See flight deals
United from PWM - See flight deals
How much will it cost to get there?
Airfare: $80+
Where can you stay?
Who will pick you up?
Pro Tip:
For avid runners, pack your running shoes and go for daily runs around the White House, Washington Monument, Lincoln and Jefferson memorials.
Chicago, Illinois (ORD, MDW) - 2 Hour 45 Minute Flight
Why go?
Food, bars, sports, rivers!
What to do?
Click here to view The BEST Things to Do in Chicago
When to go?
Summer
Who can fly you there?
AA from PWM - See flight deals
Southwest from PWM - See flight deals
United from PWM - See flight deals
How much will it cost to get there?
Airfare: $100+
Where can you stay?
Who will pick you up?
Pro Tip:
For bourbon enthusiasts, visit Untitled Supper Club on W Kinzie for an incredible speakeasy experience.
Orlando, Florida (MCO) - 3 Hour 30 Minute Flight
Why go?
Theme parks. Disney & Universal. Bring bug spray and an umbrella if you go during the summer. It's not my favorite city, but there's a reason why it's the #1 tourism city year after year in the US.
What to do?
Click here to view The BEST Things to Do in Orlando
When to go?
Year-Round
Who can fly you there?
Allegiant from PWM - See flight deals
Spirit Airways from PWM - See flight deals
Frontier from PWM - See flight deals
Southwest from PWM - See flight deals
How much will it cost to get there?
Airfare: $40+
Where can you stay?
Who will pick you up?
Philadelphia, Pennsylvania (PHL) - 1 Hour 40 Minute Flight
Why go?
History, sports, cheesesteaks
What to do?
Click here to view The BEST Things to Do in Philadelphia
When to go?
Summer and Fall
Who can fly you there?
AA from PWM - See flight deals
Spirit Airlines from PWM - See flight deals
Southwest from PWM - See flight deals
Frontier Airlines from PWM - See flight deals
How much will it cost to get there?
Airfare: $100+
Where can you stay?
Who will pick you up?
Atlanta, Georgia (ATL) - 2 Hour 50 Minute Flight
Why go?
Brew pubs, art, nightlife, Mexican food.
What to do?
Click here to view The BEST Things to Do in Atlanta
When to go?
Year-round
Who can fly you there?
Delta from PWM - See flight deals
Southwest from PWM - See flight deals
How much will it cost to get there?
Airfare: $250+
Where can you stay?
Who will pick you up?
Pro Tip:
Walk some of the BeltLine and stop at stores, bars, and restaurants.
Nashville, Tennessee (BNA) - 2 Hour 50 Minute Flight
Why go?
Music (not just country), endless bars, brewpubs, hot chicken.
What to do?
Click here to view The BEST Things to Do in Nashville
When to go?
Spring, Summer and Fall
Who can fly you there?
United from PWM - See flight deals
Southwest from PWM - See flight deals
Frontier from PWM - See flight deals
How much will it cost to get there?
Airfare: $150+
Where can you stay?
Who will pick you up?
Pro Tip:
Stay in the Gulch or near printer's alley.
Charleston, South Carolina (CHS) - 2 Hour 35 Minute Flight
Why go?
History, culture, family-friendly attractions, and water sports.
What to do?
Click here to view The BEST Things to Do in Charleston
When to go?
Spring, Summer and Fall
Who can fly you there?
AA from PWM - See flight deals
How much will it cost to get there?
Airfare: $60+
Where can you stay?
Who will pick you up?
Charlotte, North Carolina (CLT) – 2 Hour 30 Minute Flight
Why go?
Diverse Cultural Attractions, Thriving Food Scene, Outdoor Activities, Sports Hub, Historical Significance, Shopping, Festivals and Events.
What to do?
Click here to view The BEST Things to Do in Charlotte
When to go?
The best times to visit Charlotte are March–May and September–November.
Who can fly you there?
Frontier from PWM - See flight deals
AA from PWM - See flight deals
How much will it cost to get there?
Airfare: $150+
Where can you stay?
Who will pick you up?
Raleigh, North Carolina (RDU) - 2 Hour 15 Minute Flight
Why go?
Outdoors activities, restaurants, college sports, booming tech sector.
What to do?
Click here to view The BEST Things to Do in Raleigh
When to go?
Spring, Summer and Fall
Who can fly you there?
Delta from PWM - See flight deals
AA from PWM - See flight deals
Southwest from PWM - See flight deals
How much will it cost to get there?
Airfare: $30+
Where can you stay?
Who will pick you up?
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