Private Jets From Winter Haven to Hilton Head Island
Nonstop in about 1 hour and 16 minutes on the Cirrus Vision Jet.
The Better Way to Fly Private to Hilton Head Island
Fly private between Winter Haven Regional Airport - Gilbert Field (GIF) and Hilton Head Airport (HHH) aboard Flyte's Cirrus Vision Jet fleet. Featuring a whole-aircraft fare confirmed before you pay, on-demand availability, and advanced safety features.
Cirrus Vision Jet
The most advanced personal jet in the sky.
More Destinations
Hundreds of routes across Florida and beyond.
Garmin Autoland
The plane can detect an emergency and land itself.
CAPS Parachute
The only personal jet with a whole-aircraft parachute.
Private Cabin
The entire plane is yours. Four adults plus a child.
On Demand
Fly on your schedule. Any day, any time.
GIF to HHH by the Numbers
Winter Haven Regional Airport - Gilbert Field to Hilton Head Airport, nonstop on the Vision Jet.
- Flight time
- 1h 16m
- Nonstop on the Cirrus Vision Jet
- Distance
- 294 mi
- 256 nautical miles as the jet flies
- Driving
- 6h
- 359 miles by road, without stops
- Time saved
- 4h 40m
- Each way, versus driving
The Onboard Experience
Everything you need for a smoother trip between Winter Haven and Hilton Head Island.
Wi-Fi onboard
Stay connected when you need to work or relax en route, with reliable cabin Wi-Fi on available Flyte flights.
Complimentary food and beverages
Curated snacks, drinks, and light bites are included so you land refreshed.
Built-in advanced safety features
Every Flyte Vision Jet includes autoland and a whole-aircraft parachute as part of the aircraft design.
White-glove support
Our team helps coordinate any custom details so your trip stays smooth from first call to the ramp.
Things to Do in Hilton Head Island and Winter Haven
A few ways to spend your time at both ends of the flight.
Visit Coligny Beach Park
Enjoy the sun, sand, and surf at this popular beach with amenities like showers, restrooms, and nearby shops.
Explore Harbour Town
Discover the iconic red-and-white striped lighthouse, boutique shops, and waterfront dining in this charming area.
Play Golf at Harbour Town Golf Links
Tee off at one of the most famous golf courses in the country, known for hosting the RBC Heritage tournament.
Bike the Island
Rent a bike and explore over 60 miles of scenic trails that wind through the island's natural beauty.
Kayak or Paddleboard
Experience the island's waterways and wildlife by renting a kayak or paddleboard for a guided or solo adventure.
Visit the Coastal Discovery Museum
Learn about the island's history, culture, and natural environment through interactive exhibits and nature trails.
Dine at Hudson's Seafood House on the Docks
Enjoy fresh seafood with stunning views of the water at this local favorite restaurant.
Take a Dolphin Watching Tour
Join a boat tour to see playful dolphins in their natural habitat around the island.
Relax at a Spa
Indulge in a rejuvenating spa treatment at one of the island's luxurious spas.
Visit LEGOLAND Florida Resort
Enjoy a day of fun and adventure at this family-friendly theme park with rides, shows, and attractions.
Explore Bok Tower Gardens
Stroll through beautiful gardens and enjoy the serene environment and the iconic Singing Tower.
Take a Scenic Boat Tour
Experience the Chain of Lakes with a guided boat tour, offering beautiful views and local wildlife.
Visit the Polk Museum of Art
Discover a diverse collection of art exhibits ranging from contemporary to classical pieces.
Enjoy Watersports on the Lakes
Engage in activities like kayaking, paddleboarding, or fishing on the numerous lakes in the area.
Explore Downtown Winter Haven
Discover local shops, restaurants, and entertainment venues in the charming downtown area.
Other Airports Near Hilton Head Island
More Flyte network airports around Hilton Head Airport (HHH).
Savannah Hilton Head International Airport
Savannah, GA
Charleston International Airport
Charleston, SC
SUMMERVILLE
SUMMERVILLE, SC
Brunswick Golden Isles Airport
Brunswick, GA
St Simons Island Airport
St Simons Island, GA
Augusta Regional At Bush Field
Augusta, GA
FAQs
Everything you need to know about flying Winter Haven to Hilton Head Island with Flyte.
Ready to Fly to Hilton Head Island?
Book your next private flight from Winter Haven (GIF) to Hilton Head Island (HHH). Pick your date and passengers and see your whole-aircraft fare before you pay.