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Headway Enterprises Inc.

111 Avenida Menendez St.

St. Augustine, FL 32084

United States of America

Explore St. Augustine

Your Parasailing Adventure Awaits...

Embark on an exciting parasailing experience like no other with St. Augustine Parasail, the premier destination for thrilling adventures in Florida. Our experienced team ensures a safe and exhilarating ride above the beautiful waters of St. Augustine. Located on the pristine coastline, our site offers unparalleled views of the Atlantic Ocean and the charming St. Augustine skyline. We are dedicated to providing a professional and customer-focused experience that guarantees an unforgettable journey every time, catering to both beginners and thrill-seekers. Trust us to create lasting memories with a once-in-a-lifetime parasailing adventure that will stay with you forever.

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GETTING HERE

There are several ways of getting to St. Augustine Parasail depending on where you're coming from.

Our address is 111 Avenida Menendez, St. Augustine, FL 32084

"Five stars all around for St. Augustine Parasailing Company! From the moment we booked our trip online, the process was smooth and easy. The staff at the dock were friendly and professional, and they made sure we felt safe and comfortable before heading out. The parasailing ride itself was exhilarating! Soaring high above the water and seeing the coastline from a whole new perspective was incredible. We even spotted a pod of dolphins swimming alongside the boat. This is a must-do activity for anyone visiting St. Augustine!"

Teresa B

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"We decided to try parasailing with St. Augustine Parasailing Company on a whim, and it turned out to be one of the highlights of our vacation! Our family (two adults and two teenagers) had a blast. The crew was great with kids, making sure they were having fun and felt safe. The views from the parasail were amazing, and we could see for miles. We would definitely recommend this company to anyone looking for a fun and affordable activity in St. Augustine."

The Stokes

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"If you're looking for an unforgettable adventure in St. Augustine, look no further than St. Augustine Parasailing Company! We had an absolute blast parasailing with them. The crew was top-notch - they were attentive, knowledgeable, and made the whole experience a lot of fun. The parasail ride itself was smooth and scenic, and we got to see some amazing marine life from up above. This is a must-do activity for anyone visiting St. Augustine!"

Rose T

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@staugustineparasail

Tag us on Instagram with @staugustineparasail #florida #parasail

Black Friday Sale! Give the gift of flight this holiday season!🪂 Use code HOLIDAY to recieve 25% off when purchasing gift certificates online. Recipient will receive a digital gift certificate that they can use to make a reservation on the day/time of their choosing. Please keep in mind that we offer very limited winter availability with our primary season running March-September. #staugustineparasail #lovefl #beachon #blackfriday2024

School starts soon but summer is still in full swing at St. Augustine Parasail! #staugustine #oldestcity #summer #lovefl

It’s that time of year again! We will be opening for the season on Saturday, March 2nd. Reservations available online.

Last weekend of the season at St. Augustine Parasail! Thanks to everyone that joined us this year! We will be open on select days over the winter and then back full time in March 2024. #staugustineparasail

Happy 4th of July! ✌🏻🇺🇸 #staugustineparasail #4thofjuly #parasail

Smooth sailing..#staugustineparasail #summer2023 #4thofjulyweekend

Dock friend 🐢 #staugustineparasail #greenturtle #staugustinemunicipalmarina #oldestcity

Posted @withregram • @citystaugmarina Visiting St. Augustine and want to get out on the water? Stop by @citystaugmarina and take your pick on multiple options! They all offer their own unique experience on the water. Call them today to book your trip! @schoonerfreedom @blackravenpirateship @sceniccruise @staugustineparasail @staugustineecotours #citystaug #citystaugmarina

Pretty cool sight at the St. Augustine Municipal Marina as the @lanaosantamaria ship is in town for the weekend. #staugustineparasail #staugustine #lanoasantamaria

East coast sunset. #springbreak2021 #floridasunsets #staugustine #oldestcity #staugustineparasail 📸: @saltycaptjon

And we’re back! Spring season is here! #staugustineparasail #staugustinevacation #springbreak2021 #oldestcity 📸@saltycaptjon

And that will do it for the 2020 season! Thank you to everyone that flew with us this year! We will see you in the spring! #staugustineparasail #oldestcity #historiccoast #staugustine #lovefl 📸: @saltycaptjon

Ready for the 4th of July weekend ! 🇺🇸Come fly with us! #staugustineparasail #summer2020 #oldestcity #4thofjuly #bridgeoflions #loveFL 📸: @saltycaptjon

Happy Father’s Day! #staugustineparasail #summer2020 #fathersday #visitstaugustine 📸 @saltycaptjon

Summer smiles! 😄 #staugustineparasail #summervibes #staugustine #florida 📸: @saltycaptjon

Stormy start to the summer here on the Florida coast. We are looking forward to sunny skies and a fun summer here in St. Aug! 📸: @saltycaptjon #staugustineparasail #staugustine #oldestcity #debralee #shrimping #summer2020

And we are back!😎 We are excited to be open again just in time for Memorial Day Weekend! #summer2020 #staugustineparasail 📸: @saltycaptjon

We are about ready to re-open for the season after a little quarantine break! Reservations available starting on May 22nd for Memorial Day Weekend! We will be reducing our per trip capacity and maintaining strict sanitation procedures to keep our guests and our staff safe. Come fly with us this summer! #staugustineparasail #summer2020 #oldestcity #staugustine #florida

Thank you to everyone who has flown with us so far this season! It’s been fun but now it’s time to take a break while we let all this pass. We will see you all back out on the water as soon as possible! #staugustineparasail #springbreak2020 #byebyecoronavirus 📸: @saltycaptjon

#staugustineparasail #stillopen #staugustine #florida #springbreak2020 📸:@saltycaptjon

Smooth sailing today🌞 #staugustineparasail #springbreak2020 #oldestcity #floridafun 📸: @saltycaptjon

Annnnd we are ready to launch for Spring Break 2020!! Our opening day is this Sunday, March 1st. Reservations available on our website or by phone at (904)547-9608. #staugustineparasail #springbreak2020 #floridavacation #staugustine

Thank you to all our guests and staff for a great 2019 season! We will see you again in March 2020. Advance reservations for next spring and summer are available on our website. For winter parasailing please visit our sister location @daytonaparasail. #staugustineparasail #daytonaparasail #floridawinter

Last weekend of our 2019 Parasail season coming up! Come fly with us! #staugustineparasail #summer2019 #StAugustine 📸: @saltycaptjon

School may have started but it’s still summer here at #staugustineparasail! #backtoschool #floridasummer 📸@saltycaptjon

Shark week! 🦈🦈🦈 #staugustineparasail #floridasummer #sharkweek #StAugustine 📸@saltycaptjon

Summer vacation done right. #staugustineparasail #staugustinelighthouse #floridafun #summervacation 📸: @saltycaptjon

Beautiful mornings at sea. Florida summer in full effect. #staugustineparasail #summervacation #StAugustine 📸 @saltycaptjon

Off they go! #fullsend #staugustineparasail #summervacation #florida #parasail 📸: @saltycaptjon

Our dock neighbors under full sail today down by the Vilano Bridge. @schoonerfreedom #staugustineparasail #vilanobeach #schooner #tallships #sailing 📸:@saltycaptjon

Smooth sailing. #staugustineparasail #staugustine #florida #travel 📸@saltycaptjon

And they’re off!! #staugustineparasail #loveflorida #staugustine #instagood #floridatravel 📸 @saltycaptjon

Dock pal 🐢#staugustineparasail #wildlife #seaturtle #staugustine

Beautiful weather for some father’s day weekend fun! #staugustineparasail #fathersday #summertime 📸@saltycaptjon

Go away stormy skies...we’re ready to fly!!...The forecast is looking much better for the upcoming father’s day weekend! 🌞#staugustineparasail #summerstorms #municipalmarina #bridgeoflions

Flyin’ with your neighborhood friendly Spider-Man 🤟🏻#staugustineparasail #staugustine #loveflorida #spiderman 📸@saltycaptjon

Post Memorial Day weekend cleanup. Ready for summer! #staugustineparasail #catspawmarina #summertime #loveflorida #staugustine #oldestcity

Happy Memorial Day Weekend! Beautiful weather for the holiday. Come fly with us! #staugustineparasail #memorialdayweekend #summertime #loveflorida 📸: @saltycaptjon

Goiiiing up👆🏻 #staugustineparasail #loveflorida #memorialdayweekend 📸:@saltycaptjon

Ah summertime🌞. #staugustineparasail #staugustinelighthouse #summer #loveflorida 📸@saltycaptjon

Was a beautiful Mother’s day morning🌞. #staugustineparasail #happymothersday #staugustine #loveflorida 📸: @saltycaptjon

Show your mom how much you care! Mother's Day is this weekend and you know she wants to go parasailing. Enter code 'MOMS' at checkout to receive 20% off any of our parasail flights this Friday-Sunday. Book now at https://staugustineparasail.com

Dunnnn dunn dunnn dunnn dunnn dunnn dunnnnnn🦈🦈 #staugustineparasail #staugustine #loveflorida #notsharkweekyet 📸:@saltycaptjon

The Santa Maria cruised into port today. Come check it out at the City Marina! 📸: @saltycaptjon #lanaosantamaria #staugustineparasail #bridgeoflions #staugustine #tallships

Florida 🦅 #staugustineparasail #florida #osprey #schoonerfreedom @saltycaptjon

Check out the amazing views from high above St. Augustine Beach! #staugustineparasail #anastasiaisland #staugustinelighthouse #loveflorida 📸: @saltycaptjon

Smooth sailing today! #staugustineparasail #staugustine #florida #springbreak #summeriscoming

Spring mornings ☀️#staugustineparasail #northflorida #staugustine #springbreak #parasail

#Repost @saltycaptjon with @get_repost ・・・ Om nom nom. #staugustine #parasail #leroytheshark #doodoodoodoo #getsokt #flyhigh

Beautiful start to spring here in St. Augustine! #staugustineparasail #staugustine #florida #springbreak2019

Bridge of lions🦁🦁#staugustineparasail #bridgeoflions

Strumming our way into a beautiful spring! #staugustineparasail #springbreak #freetunes

Arrrrr☠️..the weather is going to shut us down for a few days but we’ll be back out there as soon as Mother Nature allows. #staugustineparasail

And up they go! #staugustineparasail #springbreak

Spring break is here and we are ready! Book online at www.staugustineparasail.com

And we are back and ready to fly for 2019! Come see us at the St. Augustine Municipal Marina right next to the Bridge of Lions.

Prepping for Spring Break. We’ll see you soon St. Augustine! #springbreak2019 #staugustine #staugustineparasail

Enjoy the St. Augustine Night of Lights this weekend! We will see you in a few months! #staugustineparasail #nightoflights

Parasail conference sunsets...ongoing education to keep parasailing safe and fun! #pos2018 #staugustineparasail

And that’s a wrap for the 2018 season for us! Thank you St. Augustine. We will see you in the spring! #staugustineparasail #bridgeoflions

Parasail season is almost over here in St. Augustine. A couple more weeks left and the forecast looks great! #staugustineparasail

More rainbow action today. 🌈Some storms brewing out in the the Atlantic but it’s beautiful off the coast of St. Augustine this weekend. #staugustineparasail

Somewhere over the 🌈! Great weather this weekend. Come fly with us! #staugustineparasail

Last week before school starts but plenty of summer fun left to be had! #staugustineparasail #staugustinelighthouse #anastasiaisland

Check this guy out! Spotted him cruising under our dock at the city marina. #staugustineparasail

This guy was keeping watch at the marina this morning👀 #staugustineparasail

We are all prepped for the 4th of July! 🇺🇸Come celebrate the holiday week with us! #staugustineparasail #bridgeoflions

Another great day at St. Augustine Parasail! Calm seas and afternoon storms holding off until after we close is what we like! #staugustineparasail

#staugustineparasail

#Repost @kayleighbryanne with @get_repost ・・・ On the lookout for JAWS #staugustineparasail

Got a little sharky out there today! 🦈😎#staugustineparasail

Show your dad how much you appreciate him with an unforgettable parasailing adventure! Use promo code 'DADS' to save 20% off all parasail flights this weekend only at St. Augustine Parasail. Thanks for all that you do, dads of the world!

Finally a nice day for parasailing! Summer is almost here! #staugustineparasail #staugustinepier

Sun’s out guns out 🌞💪🏼 #staugustineparasail

Rained out today but sunnier days ahead! 🌞#staugustineparasail

Ah now this is some parasailing weather😎 #staugustineparasail #welcometorockville #staugustinelighthouse

More poor weather this weekend. Ready to put this Spring behind us. C’mon summer!! #staugustineparasail

Finally some nice Spring weather! Great day of flying out here! #staugustineparasail

We will be closed on Thursday April 5th as we let this front pass through. We’ll see you back out there on Friday! #staugustineparasail

The weather is beautiful here in St. Augustine! Come fly with us! #staugustineparasail

Check out our new St. Augustine Lighthouse Parasail! #staugustineparasail

Here we go, St. Augustine! Spring is finally here and our season just started! Let's get out on the water and have some fun parasailing! Grab some tickets on our website at https://staugustineparasail.com.

We are opening for the season this weekend! Same office, new dock location! You’ll see our boat right next to the Bridge of Lions. #staugustineparasail

We are opening for the season this Saturday, March 10th! Reservations available on our website! #staugustineparasail

We’re getting closer to opening for the 2018 season! We are boarding on a different dock this year but the City Marina is open and busy rebuilding post Hurricane Irma.

Happy New Year! 2017 was awesome and we are on to bigger and better things in 2018! We’ll see you this spring! #staugustineparasail

Happy Thanksgiving, everyone!

Anxiously awaiting next Spring! In the meantime our Daytona Beach location is open year round! #staugustineparasail

Our season here in St. Augustine is over but there's plenty of parasailing still going with our sister company down in Daytona Beach! Head on over to daytonaparasail.com to purchase tickets. We'll be open again here in St. Augustine in the Spring of 2018.

The city of St. Augustine and the Municipal Marina sustained quite a bit of damage from Hurricane Irma so we will be forced to close early for the season. Thanks to everyone for a great first season for St. Augustine Parasail and we'll see you all in the Spring!

Boat is on the trailer and we're hunkering down for the storm. Stay safe St. Augustine!! #hurricaneirma #staugustineparasail

Celebrate your Labor Day weekend with St. Augustine Parasail! Come fly with us and save 15% off the purchase of your ticket using promo code LABORDAY2017. Book now though -- flights are selling out fast!