Today we’d like to introduce you to Taylor Withrow Michael Withrow.
Hi Taylor Withrow, we’d love for you to start by introducing yourself.
Island Head began in 2013 with just two brothers, one parasail boat, and a shared vision. At the time, we were both working in the water sports industry and had ownership in a small part of another business. But we knew we wanted to build something of our own — something we could shape from the ground up.
So, we went all in. We took a leap and launched Island Head with that single parasail boat. From day one, we focused on delivering the best possible experience on the water, and as demand grew, we reinvested into the business — adding new activities and expanding our offerings wherever we could.
Things were going well until we were unexpectedly forced out of our marina. At the time, Island Head was under contract to be sold, but when that deal fell through, we had to pivot quickly. We relocated the company and, in many ways, had to start over from scratch. It was one of the most challenging chapters in our journey, but it also ended up being one of the most defining.
Since then, we’ve steadily rebuilt — and then some. Today, Island Head operates in multiple locations, with a fleet of over 20 boats and nearly every type of water-based experience you can imagine, from laid-back private charters to adrenaline-packed adventures. It’s been a wild ride, but one we wouldn’t trade for anything.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
Not at all — the road has been anything but smooth. Like most entrepreneurs, we’ve faced our fair share of challenges. The early years were especially tough. Starting something new with limited resources meant long days on the water, managing everything ourselves, and trying to build cash flow while figuring it all out as we went.
We’ve also dealt with some major curveballs — one of the biggest being forced out of our original marina. That moment almost ended everything. The business was actually under contract to be sold at the time, and when that fell through, we had to pivot fast, relocate, and rebuild from scratch. It was a huge setback, but ultimately made us stronger.
Beyond that, building solid business relationships, earning trust in a seasonal, competitive market, and assembling a reliable team have all taken time. Hiring the right crew and creating a company culture that people want to be a part of has been one of our biggest challenges — and also one of our proudest accomplishments.
We’ve learned that challenges don’t stop as you grow — they just evolve. But every tough season has made us better at what we do.
Appreciate you sharing that. What should we know about Island Head?
Island Head is all about creating unforgettable, custom experiences on the water. We offer everything from high-energy adventures like tubing, water skiing, and parasailing to more relaxed outings like dolphin tours, kayaking, and sunset sails. We also operate scenic dinner cruises and a daily ferry service to Daufuskie Island.
Custom charters are at the heart of what we do. With a variety of boat sizes and trip styles, we build each experience around our guests — whether it’s a romantic private sail, a family adventure, or a full-day celebration on the water. No two trips are the same, and that’s exactly how we like it.
What truly sets us apart is the personal touch and the incredible team behind it all. We’ve grown from a single parasail boat to over 20 boats across multiple locations, and we now offer just about any water-based activity you can imagine — all backed by a passionate crew dedicated to delivering top-tier service.
In recent years, we’ve expanded beyond the water and moved into the broader experience business. We launched Island Head Rentals, a vacation rental management company that handles everything from oceanfront condos to high-end beach homes. Just like our on-water experiences, we bring a high standard of hospitality and care to each property we manage, making sure guests have a seamless, memorable stay from start to finish.
At Island Head, it’s never just about a rental or a boat ride — it’s about creating moments that matter. Whether on land or sea, we’re in the business of unforgettable experiences.
Who else deserves credit in your story?
We’ve had fantastic support over the years, and there’s no way we’d be where we are today without the people who believed in us and helped us grow.
Steve McNulty has played a huge role in our journey. He had the vision to build business around Daufuskie Island and became a partner in 2020. His leadership and drive have helped us expand our parasailing division into one of the island’s top-rated experiences.
We’ve also been incredibly fortunate with landlords who took a chance on us. Neil Turner and Hilton Head Harbor gave us a new home when we needed it most. Wick Scurry saw something in us early on and opened the doors for us to expand into Broad Creek Marina and establish a presence on Daufuskie Island.
Nate Jones and Ryan Luppino at Broad Creek Marina have been essential — from reliable mechanic work to providing new dock space and day-to-day support that’s helped us continue to grow. Their behind-the-scenes efforts, professionalism, and willingness to go above and beyond have been invaluable to our operation.
Our relationship with South Atlantic Bank and Bruce Yeager has also been instrumental. Their support and belief in our vision made some of our biggest steps forward possible.
We’ve also recently partnered with a former employee, Brandon Greenplate, on several real estate ventures — including the addition of our beautiful new sailboat Rosé, which has opened up even more opportunities to offer elevated, unforgettable experiences on the water.
And, of course, our team. We’ve been lucky to have some incredible staff over the years, with a few core members who’ve stuck with us through thick and thin — John Brucker, Courtney Hayes, Tim McLaughlin, Nate McNulty — and many others who’ve helped shape Island Head into what it is today.
As well as incredible family support from our parents — who stood by us on the road less traveled, especially during the difficult times when the path forward didn’t always make sense. Their belief in us meant everything.
There are countless people we could thank — partners, clients, friends, and supporters — who have played a role in our journey. It’s truly been a team effort, and we’re incredibly grateful for every one of them.
Contact Info:
- Website: https://www.islandheadhhi.com
- Instagram: https://www.instagram.com/islandhead_hhi/?hl=en
- Facebook: https://www.facebook.com/islandheadhhi/photos/?_rdr
- Youtube: https://www.youtube.com/channel/UCoulvVlTBfqsf785mV6hhyw
- Other: https://www.islandheadrentals.com
