Every Headway Enterprises brand runs its own boats, its own crews, and its own booking calendar. Book directly with the operator at the city closest to where you’re staying — pricing and flight time are nearly identical across the fleet.
Parasailing flights from the St. Augustine City Marina — over the Bridge of Lions, the Castillo de San Marcos, and Anastasia Island. USCG-licensed crew, daily departures March through October.
Daily parasailing from Ponce Inlet, minutes south of Daytona Beach. The Headway flagship — 500ft and 1,000ft flights over the Halifax River and the Atlantic, with the Ponce Inlet Lighthouse in every photo. USCG-licensed.
Guided jet ski tours past the Ponce Inlet Lighthouse, alongside dolphins and manatees in the Halifax estuary, and out to the open Atlantic. Sea-Doo Jet Skis, fully briefed, fully escorted — no experience required.
Half-day and full-day self-drive pontoon rentals. Anchor at the sandbar, drift to Disappearing Island, watch the sunset from the water. No captain's license required — we walk you through everything before you push off.
The umbrella site for everything we run out of Ponce Inlet — parasailing, jet skis, pontoon rentals, dolphin tours, kayaks, paddleboards, fishing charters, and private boat charters. Start here when you're not sure which boat you want.
Daily parasailing from Port Canaveral over Cocoa Beach and the Atlantic — plus boat-based rocket-launch viewing trips during scheduled NASA, SpaceX, and ULA launches. Closest public coastline to Kennedy Space Center.
Florida’s east coast stretches from the Georgia state line down through the Space Coast — three coastal regions, six Headway locations, one continuous Atlantic.
St. Augustine is the northernmost stop on Florida's east-coast parasailing belt. Flights launch from the City Marina, climb over the Matanzas River, and from a thousand feet up you can see the Castillo de San Marcos, the Bridge of Lions, and the full stretch of Anastasia Island. Mornings are smoothest — the inlet tightens up the wind by midday.
Daytona Beach and Ponce Inlet are the densest stretch of Headway operations — the parasail boats, jet-ski tours, pontoon rentals, dolphin tours, kayaks, and fishing charters all leave from the same marina. The Ponce Inlet Lighthouse anchors the skyline. Sandbar season runs roughly April through October, dolphins are active year-round, and the Halifax estuary is calm enough for first-time renters.
Cocoa Beach is the only stretch of Atlantic coastline within sight of Kennedy Space Center. Parasailing flights launch from Port Canaveral, overhead are cruise ships and launch pads, and during scheduled NASA, SpaceX, and ULA launches we run boat-based viewing trips that follow the launch calendar.
Headway Enterprises runs daily parasailing from four locations on Florida's east coast: St. Augustine (St. Augustine Parasail), Ponce Inlet just south of Daytona Beach (Daytona Beach Parasail and Ponce Inlet Watersports), and Cocoa Beach on the Space Coast (Cocoa Beach Parasail). Pick the closest city to where you're staying — pricing and flight length are essentially identical at each.
Across the Headway fleet, single-person flights start around $89 and tandem/triple 1,000-foot flights are typically $99–$109 per person. Photo packages are an optional add-on (around $45 per group, every flight included). Each brand site lists its current pricing — book directly with the operator at your chosen city.
Plan for about 1.5 hours on the boat with 8–10 minutes airborne. Most operators ask you to arrive 30 minutes before your scheduled departure to sign waivers and meet the crew.
Yes. Most flights require a combined rider weight of 150–450 lbs — your captain pairs riders day-of based on wind conditions and the safest tandem combination. Solo flyers need to hit the minimum on their own; large groups can split across multiple flights so everyone gets in the air.
Plenty. Ponce Inlet Jet Ski runs guided Sea-Doo tours through the inlet and Halifax estuary. Ponce Inlet Boat Rentals rents self-drive pontoons for half- and full-day trips to the sandbar. Ponce Inlet Watersports is the umbrella site for everything Ponce Inlet — including dolphin tours, kayaks, paddleboards, and fishing charters. And Cocoa Beach Parasail runs boat-based rocket-launch viewing trips during NASA, SpaceX, and ULA launches.
If the captain calls a weather cancellation, you choose between rescheduling to any available time or a full refund — same policy at every Headway location. Light rain typically isn't a problem; sustained wind and lightning are.
March through October is peak season — warmer water, calmer mornings, and the full schedule running daily. November through February is reduced-schedule but often delivers the clearest air and emptiest beaches. Book mornings whenever you can: the afternoon sea breeze stiffens up and tightens the booking window.
A short field guide to getting the most out of a parasail day on Florida’s east coast.
Florida’s east-coast sea breeze typically picks up in the early afternoon — the smoothest flights leave the dock between 9 AM and noon. Peak season is March through October. November–February runs reduced schedules but delivers the clearest air.
Combined rider weight runs 150–450 lbs across the fleet. No swimming, no experience, no jumping out of anything required. Tandems and triples are popular — kids ride strapped in next to a parent.
Reef-safe sunscreen, a towel, sunglasses with a strap, and a hat that won’t blow off. Leave big bags in the car — boat space is at a premium. Arrive 30 minutes early to sign waivers and meet the crew.
Each operator runs its own booking calendar. Click into your city to see today’s availability and reserve directly with the local crew.
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