12 of the Best Things to Do on Hilton Head in May

The kids are out of school. The sun is shining. The weather is warming up. It’s time to plan the vacation you’ve been looking forward to all year. Maybe you’re planning to spend your days laying out on the beach. Perhaps you’re feeling adventurous and would like to get out on the water. Regardless of what your interests are, you’ll find so many exciting things to do on Hilton Head in May. Read on to learn more about some of our favorite events and activities you can include in your Lowcountry getaway itinerary. Then, take a look at our free 7-Day Insider’s Guide for even more great suggestions on what to do and where to go while you’re in town. 

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12 Things You Have to Do on Hilton Head in May 

Discover for yourself what makes May one of the most popular times of year to visit Hilton Head Island! From fun in the sun to exciting events, you’re in for quite the treat! 

1. Attend the MayFest Bluffton Village Festival 

MayFest is a highly anticipated, free event that takes place in Bluffton Village each year. This unique festival celebrates local art and food. You can expect to hear live music, eat delicious treats, see beautiful art, and witness the hilarious ugly dog contest! 

2. Spend Some Time on the Beach 

There’s nothing like feeling the sun on your back and the sand between your toes while the salty air and the sound of lulling waves greet your senses. Maybe you just want to relax. Perhaps you want to get out in the water. Regardless, a day spent at the beach is never a day wasted! 

3. Visit Daufuskie Island 

A trip to Daufuskie Island is the perfect addition to your Hilton Head itinerary! Hop on the  Daufuskie ferry at Buckingham Landing, which is right at the start of the bridge connecting Bluffton to Hilton Head. From there, you will enjoy a beautiful hour-long ride through the Calibogue Sound. On the island, you can visit some of the local restaurants or enjoy a variety of outdoor activities ranging from paddleboarding and kayaking to golfing and hiking! 

4. Check out the Hilton Head Island Boat Show 

The Hilton Head Island Boat Show showcases over 80 boats over the course of two days in May. Additionally, you can find nautical lifestyle, gear, and decor, participate in demos and seminars, listen to live music, win prizes, and eat delicious food! 

5. Discover the Island’s Hidden Gems 

There’s nothing quite like the sense of serenity that washes over you while exploring the unspoiled beauty of Hilton Head Island. Audubon Newhall Preserve and Mitchelville Freedom Park are just two of our favorite hidden gems

6. Plan the Ultimate Girls Getaway 

Grab your best girlfriends and plan the trip of a lifetime. Some of the best things to do on your Hilton Head girls getaway include wine tasting, sunset cruises, spa days, beach bumming, and more! Pristine beaches, delectable dining, and exciting outdoor activities set the scene for girls who just wanna have fun! 

7. Spend Quality Time With Your Family 

If the kids’ summer break kicks off in May, then get a head start on your family vacation. Hilton Head is home to so many amazing kid-friendly activities. The Sandbox Interactive Children’s Museum, Adventure Cove, The Coastal Discovery Museum, and Zip Line & Aerial Adventures are just a few of the exciting attractions that the whole family can enjoy. 

8. Participate in the Annual Yacht Hop 

The Yacht Hop takes place every May in the Harbour Town Yacht Basin in The Sea Pines Resort. Climb aboard beautiful yachts, sample tasty hor d’oeuvres, and enjoy vibrant live music. All proceeds benefit Hospice Care of the Lowcountry’s patient care programs. 

9. Encounter Local Wildlife 

On Hilton Head Island, you will encounter unspoiled beaches, pristine waterways, and some of the most beautiful wildlife viewing opportunities on the coast. From dolphins and alligators to sea turtles and manatees, you will discover the Lowcountry’s diverse range of flora and fauna species while exploring the region. 

10. Peruse the Hilton Head Farmers Markets

Stop and shop around Hilton Head’s farmers markets for locally grown produce and ingredients, unique gifts, and tasty treats. If you’d like to cook dinner back at your family’s vacation rental, pick up some of the Lowcountry’s freshest fruits, vegetables, herbs, and other ingredients! While you’re there, be sure to strike up conversations with the local vendors, artisans, and farmers. Who knows what kinds of interesting things you’ll learn along the way? 

11. Go for a Hike Along the Best Hiking Trails 

Get outside and enjoy the fresh, salty air while hiking along the best walking trails on Hilton Head Island. Explore natural parks and preserves such as Sea Pines Forest Preserve, Audubon – Newhall Preserve, and Jarvis Creek Park. During your excursions, you might encounter fascinating landscapes and features such as maritime forests, ancient shell rings, calm bodies of water, and more! 

12. Experience the Lowcountry on a Kayak Tour

Kayaking is an excellent way to get out on the water, exercise, and explore. It’s equal parts relaxing and adventurous. This barrier island is surrounded by beautiful marshland and is the perfect setting for a kayak trip. Opt for an exciting kayak tour and experience the natural beauty of our region. 

Make the Most of Your Hilton Head Experience When You Stay in a Beach Properties Vacation Rental 

10 Cartgate Property Hilton Head private poolOnce you start planning your vacation, you’ll discover so many amazing things to do on Hilton Head in May. To make the most of your getaway, stay in a Beach Properties vacation rental. We offer a range of properties that can house multi-generational families, single families, and even families with pets! Whether you want a large, beachfront home or a small luxury condo, you’re in luck. Our properties are tastefully decorated and comfortably furnished. They often feature unique amenities such as private pools or community amenity access. Additionally, we go above and beyond to provide guests with luxury amenities across all properties. 

Are you ready to plan your May vacation? 

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