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17 Best Weekend Getaways from Hollywood, Florida (within a 4-hour flight)

  • Writer: Jordan Hinsch
    Jordan Hinsch
  • Aug 10
  • 7 min read

17 Best Weekend Getaways from Hollywood, Florida (within a 4-hour flight)
17 Best Weekend Getaways from Hollywood, Florida (within a 4-hour flight)

Hollywood, Florida, is a coastal city located between Fort Lauderdale and Miami. Known for its beautiful beaches, the Hollywood Beach Broadwalk, and vibrant arts scene, it offers a mix of relaxation and entertainment. The city features parks, golf courses, and a historic downtown area with restaurants, shops, and live music.


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 Hollywood, Florida 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.





Atlanta, Georgia (ATL) - 2 Hour 8 Minute Flight


Why go?

  • Brew pubs, art, nightlife, Mexican food.

What to do?

When to go?

  • Year-round

Who can fly you there?

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.





New York, New York (JFK, LGA, EWR, ISP, HPN) - 2 Hour 54 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?

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?

How much will it cost to get there?

  • Airfare: $20+

Where can you stay?

Who will pick you up?


Boston, Massachusetts (BOS) - 3 Hour 12 Minute Flight


Why go?

  • History and cool summertime temps!

What to do?

When to go?

  • Summer for the best weather, but peak rates for solid hotels.

Who can fly you there?

How much will it cost to get there?

  • Airfare: $27+

Where can you stay?

Who will pick you up?






Toronto, Ontario (YYZ, YTZ) - 3 Hour 15 Minute Flight


Why go?

  • Food, people, cleanliness, Hockey Hall of Fame.

What to do?

When to go?

  • Summer

Who can fly you there?

How much will it cost to get there?

  • Airfare: $16+

Where can you stay?

Who will pick you up?






Washington, DC (IAD, DCA, BWI) - 2 Hour 31 Minute Flight


Why go?

  • Museums, walking tours, great mass-transit and cherry blossoms. Fly to DCA for convenience.

What to do?

When to go?

  • Year-round (spring season for cherry blossoms)

Who can fly you there?

How much will it cost to get there?

  • Airfare: $39+

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) - 3 Hour 10 Minute Flight


Why go?

  • Food, bars, sports, rivers!

What to do?

When to go?

  • Summer

Who can fly you there?

How much will it cost to get there?

  • Airfare: $39+

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) - 2 Hour 13 Minute Flight


Why go?

  • Jazz music, other music, culture, architecture, partying, passionate football fans.

What to do?

When to go?

  • Spring, Summer, Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $49+

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.




Orlando, Florida (MCO) - 1 Hour 9 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?

When to go?

  • Year-Round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $20+

Where can you stay?

Who will pick you up?York



Philadelphia, Pennsylvania (PHL) - 2 Hour 43 Minute Flight


Why go?

  • History, sports, cheesesteaks

What to do?

When to go?

  • Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $39+

Where can you stay?

Who will pick you up?






Austin, Texas (AUS) - 2 Hour 55 Minute Flight


Why go?

  • Food, Art, Music, BBQ, Tech, Bach Parties, and All-Around Fun!

What to do?

When to go?

  • Year-Round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $49+

Where can you stay?

Who will pick you up?


Montreal, Quebec (YUL) - 3 Hour 25 Minute Flight


Why go?

  • More restaurants per capita than any other North American city.

What to do?

When to go?

  • Summer

Who can fly you there?

How much will it cost to get there?

  • Airfare: $19+

Where can you stay?

Who will pick you up?





Nashville, Tennessee (BNA) - 2 Hour 24 Minute Flight


Why go?

  • Music (not just country), endless bars, brewpubs, hot chicken.

What to do?

When to go?

  • Spring, Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $38+

Where can you stay?

Who will pick you up?

Pro Tip:

  • Stay in the Gulch or near printer's alley.


Charleston, South Carolina (CHS) - 1 Hour 33 Minute Flight


Why go?

  • History, culture, family-friendly attractions, and water sports.

What to do?

When to go?

  • Spring, Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $34+

Where can you stay?

Who will pick you up?


Quebec City, Quebec (YQB) - 3 Hour 35 Minute Flight


Why go?

  • Quebec City enchants visitors with its charming old-world atmosphere, cobblestone streets, and the historic beauty of Old Quebec, a UNESCO World Heritage site steeped in rich history and French culture.

What to do?

When to go?

  • Year-Round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $102+

Where can you stay?

Who will pick you up?


Asheville, North Carolina (AVL) - 2 Hour 4 Minute 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?

How much will it cost to get there?

  • Airfare: $39+

Where can you stay?

Who will pick you up?






Ottawa, Ontario (YOW) - 3 Hour 22 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?

When to go?

  • Year-Round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $80+

Where can you stay?

Who will pick you up?


Charlotte, North Carolina (CLT) – 2 Hour 4 Minute Flight


Why go?

  • Diverse Cultural Attractions, Thriving Food Scene, Outdoor Activities, Sports Hub, Historical Significance, Shopping, Festivals and Events.

What to do?

When to go?

  • The best times to visit Charlotte are March–May and September–November.

Who can fly you there?

How much will it cost to get there?

  • Airfare: $29+

Where can you stay?

Who will pick you up?

































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Hey! I'm Jordan, a native New Yorker who is addicted to adventure travel, photography, content creation, investing, and fitness. Read on, enjoy, and Never Run Out of First Times!

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