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?
AA from BOS- See flight deals
Delta from BOS - See flight deals
Spirit Airways from BOS - See flight deals
JetBlue from BOS - See flight deals
Frontier from BOS - See flight deals
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?
Delta from BOS - See flight deals
Spirit Airways from BOS - See flight deals
Frontier from BOS - See flight deals
Southwest from BOS - See flight deals
JetBlue from BOS - See flight deals
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?
JetBlue from BOS - See flight deals
Spirit Airways from BOS - See flight deals
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?
AA from BOS - See flight deals
Delta from BOS - See flight deals
United from BOS - See flight deals
Spirit Airways from BOS - See flight deals
JetBlue from BOS - See flight deals
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?
Air Canada from BOS - See flight deals
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?
Air Canada from BOS - See flight deals
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?
Southwest from BOS - See flight deals
AA from BOS - See flight deals
Delta from BOS - See flight deals
United from BOS - See flight deals
JetBlue from BOS - See flight deals
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?
AA from BOS - See flight deals
Southwest from BOS - See flight deals
United from BOS - See flight deals
Delta from BOS - See flight deals
JetBlue from BOS - See flight deals
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?
Delta from BOS - See flight deals
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?
JetBlue from BOS - See flight deals
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?
Delta from BOS - See flight deals
JetBlue from BOS - See flight deals
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?
Delta from BOS - See flight deals
JetBlue from BOS - See flight deals
Southwest from BOS - See flight deals
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?
JetBlue from BOS - See flight deals
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?
AA from BOS - See flight deals
Delta from BOS - See flight deals
JetBlue from BOS - See flight deals
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?
Cape Air from BOS - See flight deals
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?
JetBlue from BOS - See flight deals
Cape Air from BOS - See flight deals
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?
JetBlue from BOS - See flight deals
Cape Air from BOS - See flight deals
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?
AA from BOS - See flight deals
JetBlue from BOS - See flight deals
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?
Delta from BOS - See flight deals
JetBlue from BOS - See flight deals
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
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?
Delta from BOS - See flight deals
JetBlue from BOS - See flight deals
How much will it cost to get there?
Airfare: $200+
Where can you stay?
