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Writer's pictureJordan Hinsch

10 Best Weekend Getaways from Portland, Maine (within a 4-hour flight)


10 Best Weekend Getaways from Portland, Maine (within a 4-hour flight)
10 Best Weekend Getaways from Portland, Maine (within a 4-hour flight)

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?

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?

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?

When to go?

  • Year-round (spring season for cherry blossoms)

Who can fly you there?

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?

When to go?

  • Summer

Who can fly you there?

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?

When to go?

  • Year-Round

Who can fly you there?

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?

When to go?

  • Summer and Fall

Who can fly you there?

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?

When to go?

  • Year-round

Who can fly you there?

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?

When to go?

  • Spring, Summer and Fall

Who can fly you there?

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?

When to go?

  • Spring, Summer and Fall

Who can fly you there?

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?

When to go?

  • The best times to visit Charlotte are March–May and September–November.

Who can fly you there?

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?

When to go?

  • Spring, Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $30+

Where can you stay?

Who will pick you up?




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Hey! I'm Jordan, a native New Yorker who is addicted to adventure travel, photography, content creation, investing, and fitness. Read on, enjoy, and Never Run Out of First Times!

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