Labor Day weekend is more than just the unofficial end of summer—it’s your last big chance to unwind, explore, and escape before the pace of fall begins. Whether you’re seeking sunny beaches, mountain breezes, or vibrant city energy, your long weekend getaway deserves to be as effortless as it is memorable.
That’s where Odyssey Airways comes in.
As the Labor Day countdown begins, skip the stress of busy airports, long security lines, and unpredictable delays. With a private jet charter from Odyssey, you can fly directly to the destination of your choice—on your schedule, with comfort and personalized service every step of the way.
Here are our picks for the top Labor Day destinations in the U.S. and why flying private with Odyssey Airways makes your trip that much better.
1. Nantucket, Massachusetts – For a Classic Coastal Escape
Why go:
Nantucket is the quintessential New England summer retreat, and Labor Day is your last chance to catch it before the island winds down for fall. Cobblestone streets, historic lighthouses, and pristine beaches make this the perfect spot to unplug.
Where to stay:
The White Elephant is an iconic waterfront resort offering elegant suites and easy access to the harbor.
Where to dine:
Reserve a table at Galley Beach for sunset dining right on the sand or Straight Wharf for local seafood with flair.
Why fly private:
Nantucket Memorial Airport (ACK) can get crowded with commercial flights during peak season. Flying private gets you in and out smoothly—with no layovers or ferry transfers required.
2. Aspen, Colorado – For a Mountain Town Without the Snow
Why go:
You don’t need ski season to appreciate Aspen. In fact, the early fall shoulder season brings stunning foliage, crisp air, and far fewer crowds. Hike, bike, spa, or simply relax with a view.
Where to stay:
The Little Nell offers five-star service, mountain views, and direct access to hiking trails.
Where to dine:
Matsuhisa Aspen (from Chef Nobu Matsuhisa) blends upscale Japanese cuisine with a rustic-chic vibe.
Why fly private:
Commercial flights to Aspen can be tricky with limited availability. With Odyssey Airways, you land right at Aspen/Pitkin County Airport (ASE)—just minutes from downtown.
3. Charleston, South Carolina – For History, Hospitality, and Harbor Views
Why go:
Charleston blends historic charm with coastal elegance. Explore the cobblestone streets, visit world-class restaurants, and enjoy late-summer breezes along the Battery.
Where to stay:
Zero George Street offers boutique luxury and easy walking access to all the sights.
Where to dine:
Try FIG or Husk for creative Southern cuisine and exceptional cocktails.
Why fly private:
Skip Charleston’s busy commercial terminals and fly into Charleston Executive Airport (JZI) for quick access to downtown and nearby beaches.
4. Lake Tahoe, California/Nevada – For Mountains and Water in One Spot
Why go:
Lake Tahoe offers the best of both worlds—outdoor adventure and lakeside relaxation. Spend your days boating, paddleboarding, or hiking Emerald Bay before ending with cocktails by the water.
Where to stay:
Edgewood Tahoe is a luxurious lakeside resort with a private beach and spa.
Where to dine:
Visit Lone Eagle Grille in Incline Village for lake views and wood-fired cuisine.
Why fly private:
Arrive via Truckee Tahoe Airport (TRK), conveniently located near North Lake Tahoe resorts, without the traffic and crowds that fill the region on holiday weekends.
5. Nashville, Tennessee – For Music, Food, and Long Weekend Fun
Why go:
If you’re looking for a lively urban experience with Southern flair, Music City delivers. Nashville has become a top destination for long weekends thanks to its vibrant nightlife, award-winning dining, and live music on every corner.
Where to stay:
The Thompson Nashville in the Gulch offers boutique style, rooftop views, and walkability.
Where to dine:
Head to The Catbird Seat for a tasting menu experience or grab hot chicken at Hattie B’s.
Why fly private:
Nashville International Airport (BNA) gets packed during holiday weekends. With Odyssey, you'll use the private FBO for seamless arrival and departure—plus VIP treatment throughout.
Why Flying Private Makes a Labor Day Getaway Better
Every year, travelers scramble to book last-minute flights, fight for overhead bin space, and spend hours in crowded terminals during the Labor Day countdown. But flying private with Odyssey Airways changes everything:
- No TSA lines.
- You show up 15–30 minutes before takeoff and head straight to your aircraft.
- Your schedule, not the airline’s.
- Want to leave after work Friday and return Monday night? No problem.
- Access to regional airports.
- Reach destinations that commercial flights can’t, or get closer to your resort, beach house, or cabin.
- Total comfort and privacy.
- Stretch out, enjoy onboard refreshments, and bring everything you need—including your pet, golf clubs, or surfboard.
- White-glove coordination.
- From catering to ground transportation, Odyssey handles every detail so you can relax and focus on your getaway.
Final Thoughts
Labor Day is your last call for a summer escape—and one of the best times to treat yourself to a private flying experience. Whether you're heading for the beach, the mountains, or your favorite music city, the journey should be just as exceptional as the destination.
Let Odyssey Airways make this your smoothest—and most memorable—Labor Day yet.
