Winston-Salem, North Carolina, is a vibrant city known for its rich history, dynamic arts scene, and Southern charm. Often referred to as the "City of Arts and Innovation," it blends a legacy of tobacco and textile industries with a modern focus on healthcare, education, and technology. Visitors can explore its beautifully preserved historic district, home to Moravian architecture and cultural landmarks, while enjoying a thriving downtown filled with galleries, theaters, and eclectic dining options. With a strong connection to both the past and future, Winston-Salem offers a unique mix of tradition and innovation that appeals to residents and visitors alike.
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 Winston-Salem, North Carolina 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) - 2 Hour 5 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 CLT -Â See flight deals
American from CLT -Â See flight deals
Frontier from CLT -Â See flight deals
How much will it cost to get there?
Airfare: $50+
Where can you stay?
Who will pick you up?
Atlanta, Georgia (ATL) - 1 Hour 20 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?
Delta from GSO -Â See flight deals
How much will it cost to get there?
Airfare: $300+
Where can you stay?
Who will pick you up?
Pro Tip:
Walk some of the BeltLine and stop at stores, bars, and restaurants.
Denver, Colorado (DEN) - 3 Hour 40 Minute Flight
Why go?
Mountains, beer, National Parks, hiking, clean city, nice people.
What to do?
Click here to view The BEST Things to Do in Denver
When to go?
Year-round. Ski in the winter. Hike in the summer.
Who can fly you there?
United from CLT -Â See flight deals
American from CLT -Â See flight deals
Frontier from CLT -Â See flight deals
How much will it cost to get there?
Airfare: $130+
Where can you stay?
Who will pick you up?
New Orleans, Louisiana (MSY) - 2 Hour 5 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?
Spirit from CLT -Â See flight deals
American from CLT -Â See flight deals
Southwest from CLT -Â See flight deals
How much will it cost to get there?
Airfare: $40+
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.
New York, New York (JFK, LGA, EWR, ISP, HPN) - 1 Hour 50 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?
Click here to view The BEST Things to Do in New York
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?
American from CLT -Â See flight deals
Delta from CLT -Â See flight deals
United from CLT -Â See flight deals
Spirit Airways from CLT -Â See flight deals
JetBlue from CLT -Â See flight deals
Southwest from CLT -Â See flight deals
How much will it cost to get there?
Airfare: $40+
Where can you stay?
Who will pick you up?
Nashville, Tennessee (BNA) - 1 Hour 25 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?
American from CLT -Â See flight deals
Southwest from CLT -Â See flight deals
Frontier from CLT -Â See flight deals
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.
Orlando, Florida (MCO) - 1 Hour 45 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?
Allegiant from CLT -Â See flight deals
Spirit Airways from CLT -Â See flight deals
Frontier from CLT -Â See flight deals
Southwest from CLT -Â See flight deals
How much will it cost to get there?
Airfare: $50+
Where can you stay?
Who will pick you up?
Miami, Florida (MIA, FLL) - 2 Hour 5 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?
AA from CLT -Â See flight deals
Spirit Airways from CLT -Â See flight deals
Southwest from CLT -Â See flight deals
How much will it cost to get there?
Airfare: $40+
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.
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?
Frontier from CLT -Â See flight deals
AA from CLT -Â See flight deals
Allegiant from CLT -Â See flight deals
United from CLT -Â See flight deals
How much will it cost to get there?
Airfare: $30+
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 5 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?
Frontier from CLT -Â See flight deals
Southwest from CLT -Â See flight deals
United from GSO -Â See flight deals
How much will it cost to get there?
Airfare: $70+
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.
Philadelphia, Pennsylvania (PHL) - 1 Hour 40 Minute Flight
Why go?
History, sports, cheesesteaks
What to do?
Click here to view The BEST Things to Do in Philadelphia
When to go?
Summer and Fall
Who can fly you there?
American from CLT -Â See flight deals
Spirit Airlines from CLT -Â See flight deals
Southwest from CLT -Â See flight deals
Frontier Airlines from CLT -Â See flight deals
How much will it cost to get there?
Airfare: $70+
Where can you stay?
Who will pick you up?
Austin, Texas (AUS) - 3 Hour 8 Minute Flight
Why go?
Food, Art, Music, BBQ, Tech, Bach Parties, and All-Around Fun!
What to do?
Click here to view The BEST Things to Do in Austin
When to go?
Year-Round
Who can fly you there?
AA from CLT -Â See flight deals
Southwest from CLT -Â See flight deals
How much will it cost to get there?
Airfare: $450+
Where can you stay?
Who will pick you up?
Toronto, Ontario (YYZ, YTZ) - 2 Hour 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 CLT -Â See flight deals
American from CLT -Â See flight deals
Swoop from CLT -Â See flight deals
Flair Airlines from CLT -Â See flight deals
How much will it cost to get there?
Airfare: $350+
Where can you stay?
Who will pick you up?
Montreal, Quebec (YUL) - 2 Hour 20 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?
AA from CLT -Â See flight deals
Delta from CLT -Â See flight deals
United Airlines from CLT -Â See flight deals
Air Canada from CLT -Â See flight deals
How much will it cost to get there?
Airfare: $550+
Where can you stay?
Who will pick you up?
Charleston, South Carolina (CHS) - 1 Hour 10 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?
AA from CLT -Â See flight deals
How much will it cost to get there?
Airfare: $320+
Where can you stay?
Who will pick you up?
Cancun & Tulum, Mexico (CUN) - 3 Hour 5 Minute 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 Airways from CLT -Â See flight deals
How much will it cost to get there?
Airfare: $300+
Where can you stay?
Who will pick you up?
Asheville, North Carolina (AVL) - 1 Hour Flight
Why go?
Art, craft beer, and the Smoky Mountains. I'd recommend driving instead of flying, but it's your call!
What to do?
When to go?
Spring, Summer and Fall
Who can fly you there?
AA from CLT -Â See flight deals
How much will it cost to get there?
Airfare: $330+
Where can you stay?
Who will pick you up?
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