13 Best Weekend Getaways from Naples, Florida (within a 4-hour flight)
- Jordan Hinsch
- Aug 2
- 6 min read
Naples, Florida, is a coastal city known for its white-sand beaches, upscale shopping, and world-class golf courses. Located on the Gulf of Mexico, it offers stunning sunsets, a relaxed atmosphere, and abundant wildlife, including dolphins and manatees. Naples is also a gateway to the Everglades and features high-end dining, arts, and cultural attractions.
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 (city name) 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) - 3 Hour 11 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?
Spirit from RSW - See flight deals
JetBlue from RSW - See flight deals
How much will it cost to get there?
Airfare: $43+
Where can you stay?
Who will pick you up?
New York, New York (JFK, LGA, EWR, ISP, HPN) - 2 Hour 49 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?
Delta from RSW - See flight deals
Spirit from RSW - See flight deals
JetBlue from RSW - See flight deals
How much will it cost to get there?
Airfare: $39+
Where can you stay?
Who will pick you up?
Chicago, Illinois (ORD, MDW) - 3 Hour 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 RSW - See flight deals
Southwest from RSW - See flight deals
United from RSW - See flight deals
How much will it cost to get there?
Airfare: $54+
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.
Atlanta, Georgia (ATL) - 1 Hour 47 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 RSW - See flight deals
Frontier from RSW - See flight deals
How much will it cost to get there?
Airfare: $70+
Where can you stay?
Who will pick you up?
Pro Tip:
Walk some of the BeltLine and stop at stores, bars, and restaurants.
Washington, DC (IAD, DCA, BWI) - 2 Hour 27 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?
Spirit from RSW - See flight deals
American from RSW - See flight deals
United from RSW - See flight deals
How much will it cost to get there?
Airfare: $43+
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.
New Orleans, Louisiana (MSY) - 2 Hour 3 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?
Breeze from RSW - See flight deals
How much will it cost to get there?
Airfare: $39+
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) - 3 Hour 7 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 RSW - See flight deals
WestJet from RSW - See flight deals
Porter Airlines from RSW - See flight deals
How much will it cost to get there?
Airfare: $54+
Where can you stay?
Who will pick you up?
Philadelphia, Pennsylvania (PHL) - 2 Hour 41 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 RSW - See flight deals
Frontier from RSW - See flight deals
How much will it cost to get there?
Airfare: $65+
Where can you stay?
Who will pick you up?
Orlando, Florida (MCO) - 55 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?
Southwest from RSW - See flight deals
How much will it cost to get there?
Airfare: $89+
Where can you stay?
Who will pick you up?York
Nashville, Tennessee (BNA) - 2 Hour 10 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?
Southwest from RSW - See flight deals
How much will it cost to get there?
Airfare: $129+
Where can you stay?
Who will pick you up?
Pro Tip:
Stay in the Gulch or near printer's alley.
Montreal, Quebec (YUL) - 3 Hour 25 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?
Porter Airlines from RSW - See flight deals
How much will it cost to get there?
Airfare: $91+
Where can you stay?
Who will pick you up?
Charleston, South Carolina (CHS) - 1 Hour 33 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?
Breeze from RSW - See flight deals
How much will it cost to get there?
Airfare: $39+
Where can you stay?
Who will pick you up?
Ottawa, Ontario (YOW) - 3 Hour 19 Minute Flight
Why go?
Ottawa, Canada's capital, offers a rich tapestry of cultural institutions like museums and galleries, along with picturesque parks and the Rideau Canal, celebrated for both its summer boating and winter skating.
What to do?
Click here to view The BEST Things to Do in Ottawa
When to go?
Year-Round
Who can fly you there?
Porter Airlines from RSW - See flight deals
WestJet from RSW - See flight deals
How much will it cost to get there?
Airfare: $64+
Where can you stay?
Who will pick you up?
