Why Baby Boomers are Moving to Hilton Head Island: Insight from 53 Years of Island Living

December 2025

Booming Brilliantly—A Fresh Take on Thriving at Any Age
A Pink Special Section

By Charles Sampson

 

If you’re a Baby Boomer thinking about where to spend the next chapter of your life, Hilton Head Island, South Carolina, deserves a serious look. I say that not just as a local real
estate agent, but as someone who has lived on the Island since 1972 and has helped people reach their goals and dreams of buying and selling homes and villas here for the past 40 years.

Over the decades, my wife, Frances, and I have watched Hilton Head Island grow from a quaint coastal retreat into one of America’s top destinations for families, retirees and second homeowners. It is easy to see why—beautiful weather, low property taxes, incredible medical care, outstanding outdoor living, and a rich arts and volunteer community all help to make this Island something special and a place to call Home.

Weather and Healthier Lifestyle
One of the biggest reasons Boomers are moving to Hilton Head Island is simple, the weather.

With about 220 sunny days a year and mild winters, residents can enjoy outdoor living year-round. Forget snow shovels and icy driveways, our last major snow fall on the Island was 5-inches at Christmastime in 1989. Normal January mornings are great for walks on the beach.

An outdoor lifestyle isn’t just enjoyable, it’s healthy. From biking the 60-plus miles of Island trails to golfing, playing pickleball, walking the beach at sunset or taking the boat out on the pristine waters, staying active is a way of life here. Studies show that regular outdoor activity can add not just years, but quality years, to one’s life, and on Hilton Head Island, it feels effortless and enjoyable.

Low Property Taxes and Smart Financial Living
Another major draw for retirees is South Carolina’s low property taxes. Compared to many northern and mid-western states, one will find significant savings, which makes owning a home and living on Hilton Head Island even more appealing.
The State offers homestead exemptions and other favorable treatments for retirees, to where one can enjoy their hard-earned savings. It’s one of the many reasons people who once thought they would only vacation or winter here decide to make the Island their permanent home.

Medical Community One Can Count On
Good healthcare is essential at any stage of life, and the Hilton Head Island and Lowcountry medical community is outstanding. Novant’s Hilton Head Hospital and Coastal Carolina are complemented by Beaufort Memorial and St Joseph Candler. These facilities offer advanced care, highly regarded specialists, and emergency services that give residents peace of mind. In addition, Memorial Health in Savannah is a level-1 trauma center in case of severe injury.

Thriving Arts and Culture Scene
Hilton Head Island is so much more than beaches and golf, it’s also an Arts destination. The Arts Center of Coastal Carolina hosts concerts and produces Broadway-quality theater. The Hilton Head Symphony Orchestra, with renowned conductor John Morris Russell, performs inspiring seasonal programs, and local galleries showcase fine art from across the Lowcountry and beyond. Cultural festivals and music events fill the calendar. For Boomers who enjoy an active social life and creative expression, this community offers endless ways to connect and be inspired.

Many people who move here discover that Hilton Head Island’s spirit of community runs deep. There are dozens of volunteer opportunities, such as Volunteers In Medicine, Memory Matters, Deep Well, Habitat for Humanity and Second Helpings—just to mention a few. Giving back isn’t just appreciated—it’s part of the Island life. For retirees seeking purpose beyond relaxation, these connections make life here more meaningful.

The Hilton Head Island Lifestyle
is relaxing, connective, and enriching,
striking a perfect balance between
laid-back and lively.

Morning kayaking or a sunrise walk on the beach, lunch at Hudson’s overlooking Skull Creek, a live show at night or just a quiet evening under a moss-draped oak, the Island’s beauty and pace make it easy to feel centered, yet there’s always something to do if you want to stay busy.

Perhaps best of all, Hilton Head Island is a welcoming community where one can meet and make new friends quickly, and many will have similar stories about how they “Came for a Visit and Stayed for a Lifetime.”

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Living on Hilton Head Island for 53 years with over four decades in real estate, Charles and Frances Sampson have helped hundreds of people—many of them fellow Baby Boomers—find the right home and community. Whether you’re searching for a villa by the beach, a golf course home, or one with marsh or deep-water views, local knowledge makes all the difference. There’s no substitute for experience when it comes to understanding the nuances of each plantation, neighborhood and community. The Sampson Team know the Island inside and out—they live, work, play and raise their families here. To experience their passion in helping newcomers discover the Island lifestyle that fits them best, please call us at 843-384-7300.