String of lights over an outdoor event on Hilton Head Island

Things to Do on Hilton Head Island and in Bluffton in May

May is a gorgeous month to get outside and enjoy everything Hilton Head Island has to offer. Warm Island breezes make for enjoyable days spent outside soaking up the Lowcountry sunshine. Comfortable May evenings were made for long sunset strolls on the beach, checking out live music shows, or simply catching up with someone special–or making new friends–over frosty drinks on a cozy porch or patio. Read on to learn more about how to make the most of your time on Hilton Head Island this May, the unofficial start to summer in the South!

Morning Adult Round Robin Pickleball Clinic

Daily, 10 a.m.-12 p.m., Palmetto Dunes Pickleball Center

Spring is the perfect time to take up a new activity! This daily pickleball clinic is just the place to boost your skills and enjoy some friendly competition while playing one of the South’s most popular sports. Even if you’re new to pickleball, give it a whirl–it’s fun, it’s a great workout, and it’s a fantastic way to meet new folks on Hilton Head Island. Afterward, head to The Dunes House to refuel with a refreshing beverage and some light bites while enjoying a beautiful spring afternoon.

Sarah Ansboury Hosts Tuesday Nights Clinics

Garvin-Garvey Freedman Cottage Tour

Tuesdays and Thursdays from 10 a.m.-4 p.m., Garvin-Garvey House, Bluffton

Dating back to 1870, the Garvin-Garvey House in Bluffton is believed to be one of the earliest freedmen-owned homes on the May River. Take a 30-minute guided tour of the historic house, then stroll the shady streets of Bluffton’s Old Town district. Grab a coffee or a sweet tea, pop in and out of one-of-a-kind galleries and boutiques, and admire the stately homes designed in Carolina Lowcountry architectural style.

Stan Smith Super Series

May 17-19, Sea Pines Racquet Club

Whether you’re new to the game of tennis or have plenty of experience on the court, don’t miss this fun-filled weekend hosted by Stan Smith, The Sea Pines Resort’s touring professional. With a slew of accomplishments to his name, including being a former Wimbledon champion and coach of the U.S. Open and Olympic teams, Stan and his expert staff will offer top-notch tennis instruction and tips to help improve your game. Participants will receive a video analysis of their serve, swing instruction, strategy tips, and practice drills. Dust off your racquet and join us at Sea Pines–you’ll be all set for a successful summer on the court!

Man playing tennis

Full Moon Shore Explore

May 20 from 8:30-9:30 p.m., Sea Pines Beach Club

There’s nothing quite like experiencing the beaches of Hilton Head Island at night, lit by a full moon. The Full Moon Shore Explore lets participants explore the beaches in search of nocturnal marine life, such as ghost crabs and other sea creatures, as they move about the dunes and in the shallow surf. Reservations are required, so don’t forget to sign up early to experience this unique adventure under the light of the moon!

Gregg Russell Memorial Day Concerts

May 24 from 8-9:30 p.m., Harbour Town

Gregg Russell’s concerts are synonymous with warm spring and summer evenings at Sea Pines, and his annual Memorial Day concerts are not to be missed. Adults and children alike will be charmed and entertained by Gregg’s musical talents and lighthearted tales under the mossy oaks of Harbour Town. Kick off the summer season (unofficially) with a laid-back Lowcountry long weekend and enjoy Gregg’s songs and stories.

Shelter Cove Harbour & Hilton Head Island Art Festival

May 25 from 10 a.m.-6 p.m., Shelter Cove Harbour & Marina

Immerse yourself in Lowcountry culture! The Shelter Cove Harbour & Hilton Head Island Art Festival showcases works from more than 100 local artists, including a variety of mediums such as pottery, glass, jewelry, wood, painting, and photography. Dine on classic Southern fare as you stroll along the marina and shop for the perfect souvenir, a new piece of art for your home, or simply something special for yourself (you deserve it!)

Osprey Watch

May 29 from 3-4 p.m., Coastal Discovery Museum

Birders won’t want to miss this interesting and informative presentation about the osprey, one of Hilton Head Island’s most common birds of prey. Learn about the osprey’s nesting, migration patterns, and feeding habits, and see data from 10 years of local osprey breeding observations. After the presentation, take some time to explore the museum and discover Hilton Head Island’s natural history, heritage and culture, and ecology.

Coastal Discovery Museum

Plan your spring getaway to Hilton Head Island today!

Spring is the perfect time to discover Hilton Head Island for the first time, or come back and see us again. Order your copy of our vacation planner to help you start planning your spring getaway, and download our Island Compass App to keep you oriented once you arrive. We can’t wait to welcome you to the Lowcountry in May–see you soon!

Biking in Bluffton, SC

Find Your Island Time

Hilton Head is America’s favorite island, offering 12 miles of pristine beaches and everything you need for the ultimate retreat. Enjoy easy days relaxing in the sun, sand and surf on some of the best beaches in the country.
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