Top Private Jet Destinations in May

May brings a hint of summer without the full heat and travel congestion. With a multitude of beautiful destinations and popular events to choose from, May is quite the month for the private jet traveler.

We explore a few of our clients’ most-requested destinations – and some example itineraries by private jet charter so you might visit them too.

Ready to jet? Contact our 24/7 team at (866) 726-1222 or online for a custom quote. 

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The Bahamian Sweet Spot

Many are flocking to the Bahamas this month for a last hurrah in the sun before the heavier rains come in the summer months. There are plenty of islands and resorts to choose from – but all share the iconic white sand beaches and clear turquoise waters.


While there are many airport options (and indeed you could land directly on the water on a seaplane!) Nassau Lynden Pindling Airport is the most common landing point.

Sample Itinerary:

Chicago – Nassau

Aircraft: Hawker 800 (or similar)
Seats: 8
Flight Time: 3 hrs
Estimate Cost: $22,000 – $26,000 (one way)

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Break Out Your Big Hat for the Derby

The Kentucky Derby (May 3) is the premiere horse-racing event of the season – and the kick-off to the Triple Crown, which includes the Preakness Stakes & the Belmont Stakes. Sip an iconic Mint Julep, place your bets, and may the fastest horse win!

PrivateFly Kentucky Derby Flights

Image Source: Kentucky Derby

Private jets can land at either Louisville International Airport or Louisville Bowman Airport.

Sample Itinerary:

Los Angeles – Louisville

Aircraft: Challenger 601 (or similar)
Seats: 9
Flight Time: 4 hrs
Estimate Cost: $33,500 – $38,000 (one way)

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Festivities in Portland

Explore Portland, Oregon in early May while the town gathers in Tom McCall Waterfront Park to celebrate Cinco de Mayo with food, drinks, live music, and of course – plenty of tequila.

Later in the month, catch the Portland Rose Festival for fresh blooms – or the annual Fleet Week on the final weekend.

Portland Oregon Collage_600x400

The best private jet airport option in Portland is Portland International Airport.

Sample Itinerary:

Dallas – Portland

Aircraft: Citation III (or similar)
Seats: 8
Flight Time: 3 hrs 45 min
Estimate Cost: $28,650 – $34,000 (one way)

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A Mother’s Day Retreat in Asheville

Nestled in the North Carolina Blue Ridge Mountains, Asheville is a charming town with a vibrant arts scene and historic architecture.

For Mother’s Day, plan a weekend getaway to the nearby Biltmore Estate – complete with wine-tasting, spas, and fresh blooms galore.

Biltmore Estate Collage_600x400

The best private jet airport in Asheville is Asheville Regional Airport, a quick 20 minute drive to the Biltmore Estate.

Sample Itinerary:

New York City – Asheville

Aircraft: Falcon 2000 (or similar)
Seats: 10
Flight Time: 1 hr 45 min
Estimate Cost: $19,430 – $25,000 (one way)

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Culture in the French Riviera

For the film aficionado, the Cannes Film Festival (May 14 – 25) is a premiere event to attend. However, for those with conflicting interests, the nearby Monaco Grand Prix will take place May 23 – 26. PrivateFly can assist with a helicopter transfer into Monte Carlo so that you never skip a beat.

Cannes Film Fest and Monaco Grand Prix Collage_600x400

The best private jet airport to start this French getaway is Cannes Mandelieu or Nice Cote D’Azur.

Sample Itinerary:

London – Cannes

Aircraft: Citation XLS (or similar)
Seats: 8
Flight Time: 1 hr 25 min
Estimate Cost: $16,970 – $20,000 (one way)

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Memorial Day Weekend in the Northeast

Memorial Day Weekend is the unofficial start to summer – spend it in one of the quaint Northeastern beach towns like Montauk or Nantucket. Reaching these islands or coastal towns is a breeze by private jet charter, as we can get you into the smaller airports and shorten your overall travel time.

Nantucket 4th of July_600x400

Fly into Nantucket Memorial Airport for quick access to the destination. On Long Island, private jets and turboprops can land at East Hampton Airport or Montauk Airport. Please note that Martha’s Vineyard Airport will be closed until May 15.

Sample Itinerary:

Washington DC – Nantucket

Aircraft: Nextant 400XTi (or similar)
Seats: 6
Flight Time:  1 hr 20 min
Estimate Cost: $10,680 – $15,000 (one way)

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Ready to fly? Call our 24/7 team at (866) 726-1222 or contact us online for a custom private jet charter quote to any global destination.