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The Cypress of Hilton Head Island An Award-winning Continuing Care Retirement Community


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Culture, recreation and entertainment abound in a 10-mile radius from your home

Hilton Head Island and our surrounding cities exude history, entertainment and beauty. With our close proximity to Beaufort, South Carolina, Charleston, South Carolina and Savannah, Georgia, a wealth of fun and adventure awaits with carriage rides, walking tours and Southern charm.


Did you know that Lowcounty is home to several premier art galleries that Cypress residents can enjoy, rain or shine? Each museum showcases different mediums of art and features artists both local and well-known. Some galleries even offer classes to teach art lovers how to paint, draw and create. See what amazing spectacles are ahead of you at one of our many Hilton Head museums!

The Art League of Hilton Head

Are you a talented artist or interested in learning? Check out the opportunities available at The Art Academy. You can become a member, take art classes or visit the gallery and support local artists in your community.

Walter Greer Gallery

The Walter Greer Gallery is a popular destination for art enthusiasts and collectors alike.  In addition to showcasing different esteemed artists, you can also explore their halls, which are filled with local art. Follow their upcoming exhibits and special events for a fun night on the town!

Performing Arts

You wouldn’t believe the talent in Hilton Head, SC. In fact, you’ll have to hear it to believe it! The Cypress of Hilton Head has numerous performing arts centers within ten miles of our campus that deliver inspiring and emotional performances throughout the week. Check out each center’s programming schedule here, and plan your trip to the theater today!

The Arts Center of Coastal Carolina

From theater performances to special events, there’s always something exciting on stage at The Arts Center of Coastal Carolina! Enjoy a fun night out with family or friends at one of our local venues.

The Elizabeth Wallace Theater

The Elizabeth Wallace Theater is a theater run by The Arts Center of Coastal Carolina. Here you can find a stacked line up of Broadway’s top shows. See what exciting performances they have slated for this year!

Hilton Head Symphony Orchestra

Their tagline says it all, “inspiring, enriching and uniting the Lowcountry.” You don’t want to miss a show featuring the beautiful string and percussion sounds of Hilton Head’s Symphony Orchestra. Whether you want to enjoy music at their “Symphony Under the Stars” or another upcoming event, follow their full calendar to catch a future performance.

Hilton Head Choral Society

The Hilton Head Symphony Orchestra was created in 1975 and has grown musically and by numbers ever since. Starting with a performance of Handel’s Messiah, their repertoire now includes classical, contemporary and seasonal works.

Hilton Head Barbershoppers

Who doesn’t love a cappella harmony? The all-male chorus and quartets performs at different venues for businesses, non-profits and individuals around Lowcountry.

Hallelujah Singers

The Hallelujah Singers perform soulful and passionate renditions of gospel music at weddings, conventions, churches and more. Visit their website to book their talent or find a performance!

Outdoor Activities and Events

There is no place like Lowcounty. In our beautiful corner of South Carolina, our island’s moderate temperatures allow residents to have something to look forward to outdoors every season. On warmer or even brisk days, our residents can enjoy the weather with a long list of outdoor adventures and activities. From recreation areas to miles of gorgeous Hilton Head shoreline, Cypress residents can maintain a healthy, active lifestyle close to home while adoring the beautiful landscape in Lowcountry.

12 miles of beach

Go for a swim or walk along the beautiful beaches that run for miles along the Atlantic Ocean.

Over 50 miles of bike trails

Do you enjoy exercising outdoors? Breath in the fresh air and enjoy a long bike ride or casual stroll along Hilton Head’s public pathways.

RBC Heritage PGA Golf Tournament

If you live on Hilton Head Island, chances are you enjoy golf or have tried swinging a club at one of our many surrounding golf courses. Watch the pros battle it out at the RBC Heritage PGA Golf Tournament right in our backyard! For one week each year, you can enjoy the event as a spectator or volunteer.


What are you craving for dinner? Lowcountry hosts a lively restaurant scene with hundreds of casual and fine-dining restaurants to choose from. Perfect for any palate, our delicious restaurants have unique menus to satisfy even the pickiest of eaters. Whether you’re looking for fresh seafood or a cultural taste, find a restaurant that catches your eye here.

250 Restaurants

Try different cuisines from around the world and find your favorite “local” joint near your home on Hilton Head Island. It may take some time to work through the 250+ restaurants available in our area, but you can make a reservation to get started tonight!


For many, continued education is a very important part of aging. Luckily, there are opportunities for seniors to keep learning past the “traditional” schooling years. What better way to fill your empty time in retirement than following a passion? Explore the schools and programs in our area to find the right fit for you!

The University of South Carolina Beaufort

The University of South Carolina Beaufort has three campuses in the Carolina Sea Islands, including one on Hilton Head Island with a focus on hospitality management.





The Cypress of Hilton Head | 20 Ladyslipper Lane, Hilton Head Island, SC 29926

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We are so excited to see those beautiful Spring blooms throughout our Hilton Head community! 💐We have an abundance of natural beauty around our community and retirement is the perfect time to take advantage of it.Learn more about the benefits of retiring on Hilton Head Island: #RetirementCommunity #RetirementLiving #Seniors #SeniorLiving #HiltonHead #HHI


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The Cypress of Hilton Head Island is located at 20 Ladyslipper Lane, Hilton Head Island, SC 29926, within Hilton Head Plantation.

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