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  • Writer's pictureJordan Hinsch

21 Best Weekend Getaways from Boston (within a 4 hour flight)

Updated: Jan 21



Boston is a beautiful city in itself, particularly in the summer. As a resident, you may find it difficult to ever leave, but Boston has long winters and time away down south might be essential for you.


With a vast array of short domestic destinations, there are also many international destinations within reach. Here are some weekend getaway ideas for locals in the Boston area within a 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 what you want to do at your destination.


Miami, Florida (MIA, FLL) - 3.5 Hour Flight


Why go?

  • Beaches, outdoors activities, clubs, restaurants, culture. I just ask that you please please please venture out beyond Miami Beach.

When to go?

  • Any time of the year, but best is October - February for perfect weather.

Who can fly you there?

How much will it cost to get there?

  • Airfare: $100+

Where can you stay?

Pro Tip:

  • Visit the following neighborhoods to step away from the "typical Miami": Wynwood, Brickell, Coral Gables, Coconut Grove, Midtown, Edgewater.



Orlando, Florida (MCO) - Just Over a 3 Hour Flight


Why go?

  • Disney & Universal Studios. Bring bug spray and an umbrella if you go during the summer.

When to go?

  • Year-Round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $100+

Where can you stay?





Puerto Rico - 4 Hour Flight to San Juan (SJU)


Why go?

  • Surfing, culture, and hiking. Oh and you don't need a passport to travel.

When to go?

  • December to July to avoid hurricanes and tropical storms.

  • April to June to avoid the busy winter and the upcoming rainy season.

Who can fly you there?

How much will it cost to get there?

  • Airfare: $200+

Where can you stay?




New York, New York (JFK, LGA, EWR, ISP, HPN) - 1.5 Hour Flight


Why go?

  • Sure, many Boston residents come from New York. Why not go back for a nice weekend during the summer to see the sights in the city that never sleeps? Or take a trip during the holiday season and see the tree at Rockefeller Center and a Broadway play.

When to go?

  • Summer for the best weather, but 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?




Toronto, Ontario (YYZ) - Just Under a 2 Hour Flight


Why go?

  • Food, people, cleanliness, Hockey Hall of Fame.

When to go?

  • Summer

Who can fly you there?

How much will it cost to get there?

  • Airfare: $200+

Where can you stay?




Montreal, Quebec (YUL) - 1.5 Hour Flight


Why go?

  • More restaurants per capita than any other North American city.

When to go?

  • Summer

Who can fly you there?

How much will it cost to get there?

  • Airfare: $300+

Where can you stay?





Washington, DC (IAD, DCA, BWI) - 1.5 Hour Flight


Why go?

  • Museums, walking tours, great mass-transit and cherry blossoms. Fly to DCA for convenience.

When to go?

  • Year-round (spring season for cherry blossoms)

Who can fly you there?

How much will it cost to get there?

  • Airfare: $100+

Where can you stay?

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) - Just Under a 3 Hour Flight


Why go?

  • Food, bars, sports, rivers!

When to go?

  • Summer

Who can fly you there?

How much will it cost to get there?

  • Airfare: $100+

Where can you stay?

Pro Tip:

  • For bourbon enthusiasts, visit Untitled Supper Club on W Kinzie for an incredible speakeasy experience.




Kansas City, Missouri (MCI) - 3.5 Hour Flight


Why go?

  • BBQ! BBQ! BBQ!

When to go?

  • Year-round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $500+

Where can you stay?

Pro Tip:

  • Visit the Power & Light District for a unique nightlife experience & go to Arthur Bryant's for BBQ.




Bermuda (BDA) - 2 Hour Flight


Why go?

  • Pink sand beaches and diving.

When to go?

  • Year-round (might want to avoid hurricane season)

Who can fly you there?

How much will it cost to get there?

  • Airfare: $400+

Where can you stay?


Charleston, South Carolina (CHS) - 2.5 Hour Flight


Why go?

  • History, culture, family-friendly attractions, and watersports.

When to go?

  • Spring, Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $200+

Where can you stay?


Nashville, Tennessee (BNA) - 2.5 Hour Flight


Why go?

  • Music (not just country), endless bars, brewpubs, hot chicken.

When to go?

  • Spring, Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $300+

Where can you stay?

Pro Tip:

  • Stay in the Gulch or near printer's alley.




New Orleans, Louisiana (MSY) - 3.5 Hour Flight


Why go?

  • Jazz music, other music, culture, architecture, partying, passionate football fans.

When to go?

  • Spring, Summer, Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $300+

Where can you stay?

Pro Tip:

  • Check out Bourbon Street for a little bit, but don't get sucked in. It's absolutely disgusting. Chartres Street is better for those looking to maintain their cleanliness.



Austin, Texas (AUS) - Just Over a 4 Hour Flight


Why go?

  • Food, Art, Music, BBQ, Tech, Bach Parties, and All-Around Fun!

When to go?

  • Year-Round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $300+

Where can you stay?




Portland, Maine (PWM) - Just Under a 1 Hour Flight


Why go?

  • Seaside villages and towns with incredible restaurants and a thriving art scene.

When to go?

  • Summer

Who can fly you there?

How much will it cost to get there?

  • Airfare: $250+

Where can you stay?




Nantucket, Massachusetts (ACK) - Just Under a 1 Hour Flight


Why go?

  • Fresh seafood, winding beaches, cozy BnBs, and loads of summer activities.

When to go?

  • Summer

Who can fly you there?

How much will it cost to get there?

  • Airfare: $200+

Where can you stay?




Martha's Vineyard, Massachusetts (MVY) - 45 Minute Flight


Why go?

  • Rolling hills, towering bluffs, cultural events, and loads of summer activities.

When to go?

  • Summer

Who can fly you there?

How much will it cost to get there?

  • Airfare: $150+

Where can you stay?




Philadelphia, Pennsylvania - 1.5 Hour Flight


Why go?

  • History, sports, cheesesteaks

When to go?

  • Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $150+

Where can you stay?




Atlanta, Georgia (ATL) - Just Over a 2.5 Hour Flight


Why go?

  • Brew pubs, art, nightlife, Mexican food.

When to go?

  • Year-round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $100+

Where can you stay?

Pro Tip:

  • Walk some of the BeltLine.




Newport, Rhode Island - 2 Hour Drive


Newport, Rhode Island
Newport, Rhode Island

Why go?

  • Cliff Walk, music festivals, boutique stores and inns.

When to go?

  • Spring, Summer and Fall

Where can you stay?




Raleigh, North Carolina (RDU) - 2 Hour Flight


Why go?

  • Outdoors activities, restaurants, college sports, booming tech sector.

When to go?

  • Spring, Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $200+

Where can you stay?




Comments


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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