Miami, FL

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

Jordan Hinsch

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

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 any 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.


Bear in Mind: When travelling internationally as of June 14th, 2021, you're required to present a negative Covid-19 PCR test upon return to the United States. This is on top of any restrictions in the country you are visiting. Since the rules are changing frequently, I'll leave that out. Instead, I'll include a link to the embassy site where you can find the latest information.

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

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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?

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Jordan Hinsch is a sales expert, blogger, investor, photographer, videographer, and outdoors enthusiast. Primarily known for unique travel and bucket list related content, Jordan also specializes in lifestyle, fitness, and finance. Follow him here on NewsBreak and on Instagram & Pinterest @neverjordinary.

Miami, FL
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