St. Augustine
St. Augustine Parasail
Parasailing over the nation's oldest city.
Parasailing flights from the St. Augustine City Marina — over the Bridge of Lions, the Castillo de San Marcos, and Anastasia Island. USCG-licensed crew.
Parasailing
Who we are
One company, a coastline of experiences.
Headway Enterprises, Inc. is headquartered at the Ponce Inlet marina in Volusia County, Florida. We own and operate the boats, the crews, and the storefronts behind a family of watersports and hospitality brands stretching across three regions of Florida’s Atlantic coast.
Each brand carries its own name and runs its own daily operation — but shares a single corporate backbone for safety, licensing, marketing, customer care, and secure online booking. That structure lets a small local crew deliver a big, dependable experience, whether you’re lifting off over the nation’s oldest city or watching a rocket climb from the water off Cape Canaveral.
The portfolio
Our brands.
Every Headway Enterprises brand runs its own boats, crews, and booking calendar. Visit a brand to see live availability and book directly with the local operation.
Ponce Inlet
Daytona Beach Parasail
Florida's flagship parasailing operator.
Daily parasailing from Ponce Inlet, minutes south of Daytona Beach. 500ft and 1,000ft flights over the Halifax and the Atlantic, with the Ponce Inlet Lighthouse in every photo.
Parasailing
Ponce Inlet
Ponce Inlet Jet Ski
Guided Sea-Doo expeditions through Ponce Inlet.
Guided jet ski tours past the Ponce Inlet Lighthouse, alongside dolphins and manatees, and out to the open Atlantic. Sea-Doo Jet Skis, fully briefed, fully escorted.
Jet Ski Tours
Ponce Inlet
Ponce Inlet Boat Rentals
Self-drive pontoons on the Halifax River.
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.
Pontoon Rentals
Ponce Inlet
Ponce Inlet Watersports
Every Ponce Inlet activity in one place.
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.
ParasailingJet SkiPontoonsDolphin ToursFishingKayaksPaddleboards
Ponce Inlet
Inlet Ice Cream
Your neighborhood ice cream shop.
Hand-dipped ice cream, sherbet, Italian ice, smoothies, and custom party desserts — right at the Inlet Marina, next to the boats.
Ice CreamSherbetItalian IceCustom Cakes
Cape Canaveral
Cocoa Beach Parasail
Parasailing & rocket-launch tours from the Space Coast.
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.
ParasailingRocket Launch Tours
Where we operate
Three regions of Florida’s east coast.
From the Georgia state line down to the Space Coast — Headway brands run along a continuous stretch of the Florida Atlantic.
St. Augustine
America's Oldest City · Northeast Florida
Our northernmost operation runs parasailing flights from the St. Augustine City Marina — over the Matanzas River, the Castillo de San Marcos, and Anastasia Island. St. Augustine Parasail anchors the Headway footprint on Florida's First Coast.
- St. Augustine Parasail — parasailing
Daytona Beach & Ponce Inlet
Volusia County · Headway HQ
The Ponce Inlet marina is the heart of Headway Enterprises — our corporate HQ and the densest cluster of operations. Parasailing, jet ski tours, pontoon rentals, dolphin tours, fishing charters, and our Inlet Ice Cream shop all run from the same peninsula, minutes south of Daytona Beach beneath the Ponce Inlet Lighthouse.
- Daytona Beach Parasail — parasailing
- Ponce Inlet Jet Ski — jet ski tours
- Ponce Inlet Boat Rentals — pontoon rentals
- Ponce Inlet Watersports — parasailing, jet ski, pontoons, dolphin tours, fishing, kayaks, paddleboards
- Inlet Ice Cream — ice cream, sherbet, italian ice, custom cakes
Cocoa Beach & The Space Coast
Cape Canaveral · Brevard County
On the Space Coast, Cocoa Beach Parasail flies from Port Canaveral over the only stretch of Atlantic coastline within sight of Kennedy Space Center — and runs boat-based viewing trips during scheduled NASA, SpaceX, and ULA launches.
- Cocoa Beach Parasail — parasailing, rocket launch tours
About the company
Frequently asked questions.
What is Headway Enterprises, Inc.?
Headway Enterprises, Inc. is a Florida company headquartered at the Ponce Inlet marina in Volusia County. We own and operate a portfolio of parasailing, jet ski, boat rental, watersports, and dessert brands along Florida's east coast, from St. Augustine to Cocoa Beach.
Which brands does Headway Enterprises operate?
Our brands include St. Augustine Parasail, Daytona Beach Parasail, Ponce Inlet Jet Ski, Ponce Inlet Boat Rentals, Ponce Inlet Watersports, Inlet Ice Cream, and Cocoa Beach Parasail. Each runs its own boats, crews, and booking calendar, supported by a shared Headway corporate team.
Where is Headway Enterprises located?
Our corporate headquarters is at 4936 S. Peninsula Dr., Ponce Inlet, FL 32127 — on the marina that hosts the majority of our watersports operations. Our brands operate across three Florida coastal regions: Northeast Florida, Volusia County, and the Space Coast.
How do I book a parasailing flight or watersports activity?
Book directly with the brand operating in the city you're visiting. Each Headway brand has its own website with live availability and online booking. Visit the brand from the portfolio above, or contact our corporate office and we'll point you to the right operator.
Are Headway Enterprises operations licensed and insured?
Yes. Our parasailing and watersports operations run with U.S. Coast Guard–licensed crews and carry the licensing and insurance required to operate commercial vessels and watercraft in Florida waters. Safety is coordinated across all brands by the Headway corporate team.
What is your payment and refund policy?
Bookings are paid securely online at the time of reservation through each brand's booking system, operated by Headway Enterprises. If a captain cancels a trip for weather or safety, customers may reschedule to any available time or receive a full refund. Specific terms are shown at checkout for each brand.
How do I reach Headway Enterprises corporate?
For corporate, press, partnership, or vendor inquiries, email info@headwayenterprises.com or write to Headway Enterprises, Inc., 4936 S. Peninsula Dr., Ponce Inlet, FL 32127. For booking or trip-specific questions, contact the individual brand operator directly.
Get in touch with Headway.
For bookings, reach the brand operating in your city. For corporate, press, partnership, or vendor inquiries, contact our Ponce Inlet headquarters.
Headway Enterprises, Inc. · 4936 S. Peninsula Dr., Ponce Inlet, FL 32127