15 Best Weekend Getaways from Greenwich, Connecticut (within a 4-hour flight)
- Jordan Hinsch
- 16 hours ago
- 7 min read
Greenwich, Connecticut, is a wealthy coastal town in Fairfield County, known for its upscale neighborhoods, scenic waterfront, and proximity to New York City. It features high-end shopping, historic sites, and excellent schools, making it a desirable place to live.
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 Greenwich, Connecticut, 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.
Boston, Massachusetts (BOS) - 1 Hour 15 Minute Flight
Why go?
History and cool summertime temps!
What to do?
Click here to view The BEST Things to Do in Boston
When to go?
Summer for the best weather, but peak rates for solid hotels.
Who can fly you there?
Delta from JFK - See flight deals
JetBlue from JFK - See flight deals
American from JFK - See flight deals
How much will it cost to get there?
Airfare: $89+
Where can you stay?
Who will pick you up?
Miami, Florida (MIA, FLL) - 3 Hour 6 Minute Flight
Why go?
Beaches, outdoors activities, clubs, restaurants, culture. I just ask that you please please please venture out beyond Miami Beach.
What to do?
Click here to view The BEST Things to Do in Miami
When to go?
Any time of the year, but best is October - February for perfect weather. Avoid the spring break crowd in late Feb/early March the best you can.
Who can fly you there?
Frontier from JFK- See flight deals
Delta from JFK - See flight deals
JetBlue from JFK - See flight deals
How much will it cost to get there?
Airfare: $27+
Where can you stay?
Who will pick you up?
Pro Tip:
Visit the following neighborhoods to step away from the "typical Miami": Wynwood, Brickell, Coral Gables, Coconut Grove, Midtown, Edgewater.
Orlando, Florida (MCO) - 2 Hour 51 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?
JetBlue from JFK - See flight deals
Delta from JFK - See flight deals
Frontier from JFK - See flight deals
How much will it cost to get there?
Airfare: $44+
Where can you stay?
Who will pick you up?York
Atlanta, Georgia (ATL) - 2 Hour 35 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?
Frontier from JFK - See flight deals
JetBlue from JFK - See flight deals
Delta from JFK - See flight deals
How much will it cost to get there?
Airfare: $29+
Where can you stay?
Who will pick you up?
Pro Tip:
Walk some of the BeltLine and stop at stores, bars, and restaurants.
Chicago, Illinois (ORD, MDW) - 2 Hour 39 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?
JetBlue from JFK - See flight deals
Delta from JFK - See flight deals
American from JFK - See flight deals
How much will it cost to get there?
Airfare: $69+
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.
New Orleans, Louisiana (MSY) - 3 Hour 27 Minute Flight
Why go?
Jazz music, other music, culture, architecture, partying, passionate football fans.
What to do?
Click here to view The BEST Things to Do in New Orleans
When to go?
Spring, Summer, Fall
Who can fly you there?
JetBlue from JFK - See flight deals
Delta from JFK - See flight deals
How much will it cost to get there?
Airfare: $79+
Where can you stay?
Who will pick you up?
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.
Toronto, Ontario (YYZ, YTZ) - 1 Hour 45 Minute Flight
Why go?
Food, people, cleanliness, Hockey Hall of Fame.
What to do?
Click here to view The BEST Things to Do in Toronto
When to go?
Summer
Who can fly you there?
Air Canada from JFK - See flight deals
American from JFK - See flight deals
Flair Airlines from JFK - See flight deals
How much will it cost to get there?
Airfare: $16+
Where can you stay?
Who will pick you up?
Washington, DC (IAD, DCA, BWI) - 1 Hour 25 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?
Delta from JFK - See flight deals
American from JFK - See flight deals
How much will it cost to get there?
Airfare: $46+
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.
Nashville, Tennessee (BNA) - 2 Hour 34 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?
JetBlue from JFK - See flight deals
American from JFK - See flight deals
How much will it cost to get there?
Airfare: $46+
Where can you stay?
Who will pick you up?
Pro Tip:
Stay in the Gulch or near printer's alley.
Montreal, Quebec (YUL) - 1 Hour 27 Minute Flight
Why go?
More restaurants per capita than any other North American city.
What to do?
Click here to view The BEST Things to Do in Montreal
When to go?
Summer
Who can fly you there?
Air Canada from JFK - See flight deals
How much will it cost to get there?
Airfare: $109+
Where can you stay?
Who will pick you up?
Cancun & Tulum, Mexico (CUN) - 4 Hour Flight
Why go?
Your money goes a long way in Cancun: all-inclusive hotels, nightlife, and activities.
Your money doesn’t go very far in Tulum: boutique hotels (some are grossly overpriced), many hotels have no air conditioning, taxis and bike rentals will try to rip you off.
If you’re looking for clubs and nightlife, go to Tulum Beach.
If you’re looking for culture and less expensive eats, go to Tulum Centro.
Tulum is actually a great experience if you have the right mindset going into your vacation.
What to do?
Click here to view The BEST Things to Do in Cancun
Click here to view The BEST Things to Do in Tulum
When to go?
December to April for the best weather.
Avoid March Spring Break travel if you want to be at peace.
Who can fly you there?
American from JFK - See flight deals
How much will it cost to get there?
Airfare: $207+
Where can you stay?
Who will pick you up?
Charleston, South Carolina (CHS) - 2 Hour 12 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?
JetBlue from JFK - See flight deals
Delta from JFK - See flight deals
How much will it cost to get there?
Airfare: $74+
Where can you stay?
Who will pick you up?
Bermuda (BDA) - 2 Hour 5 Minute Flight
Why go?
Pink sand beaches and diving.
What to do?
Click here to view The BEST Things to Do in Bermuda
When to go?
Year-round (might want to avoid hurricane season)
Who can fly you there?
American from JFK - See flight deals
How much will it cost to get there?
Airfare: $114+
Where can you stay?
Who will pick you up?
Charlotte, North Carolina (CLT) – 2 Hour 3 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?
American from JFK - See flight deals
Delta from JFK - See flight deals
How much will it cost to get there?
Airfare: $90+
Where can you stay?
Who will pick you up?
Kansas City, Missouri (MCI) - 3 Hour 30 Minute Flight
Why go?
BBQ! BBQ! BBQ!
What to do?
Click here to view The BEST Things to Do in Kansas City
When to go?
Year-round
Who can fly you there?
Delta from JFK - See flight deals
How much will it cost to get there?
Airfare: $99+
Where can you stay?
Who will pick you up?
Pro Tip:
Visit the Power & Light District for a unique nightlife experience & go to Arthur Bryant's for BBQ.
