10 Memorable Things to Do on a Trip to Hilton Head Island

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There are certain moments during family vacations that are more memorable than others. But why is that? Was it a unique experience? A hilarious moment? Did extended family you hardly ever see make the memory special? Were there new friends made?

Our goal in writing this guide was to think up as many opportunities for those moments that make you say, “Remember when,” for years to come.

Dolphins swimming through the intracoastal waterway

Spot Your First Dolphin

This is something that can be done year-round and will most likely happen without even trying. Your first chance will be catching a glance at dolphins beneath the two bridges as you arrive, but if you keep an eye out on your beach days, you’ll likely see them swimming past the shoreline. The first sighting is always exciting, so you won’t help announcing to the group, “Look! Dolphins!”

If the random dolphin sighting just won’t do, there are multiple ways to create an even more memorable experience. Any excursion out on the water will allow for more chances to spot these playful creatures, but if that’s your prime goal, opt to book a Dolphin Cruise. There are so many to choose from, so read this guide to help narrow down which cruise works best with your group and schedule.

Another great way to see dolphins is on a kayak tour. These journeys through the marsh are not only relaxing, but a dolphin will most likely pass you at a closer distance than if you were on a jet ski or boat. And when that happens, it’s a pretty special moment that you won’t soon forget!

Take a Segway Tour

You might associate Segway tours with bigger cities, but Hilton Head Island offers many opportunities to try this unique way of getting around and seeing the sights! With Hilton Head Segway, you can explore Historic Mitchelville, Shelter Cove, and other beautiful island parks and pathways.

One of the favorite tours that is offered, is the Eco Fun Ride, a tour that combines learning about the local wildlife while giving you plenty of time to ride the trails and boardwalks through the Coastal Discovery Museum and Jarvis Creek Park. On this ride, you’ll pass through Honey Horn’s beautiful gardens, see a Marsh Tacky Horse, the property’s Butterfly House, and have opportunities to see alligators. Hard-to-please teenagers have often been known to gush over how cool this tour is—just sayin’!

Unsplash | Colter Olmstead

Go on a Fishing Excursion

Not something you get to do every day—or even every vacation—is embarking on a private fishing charter. Not only could this be your group’s chance to get out on the beautiful waters surrounding Hilton Head, but your boat will be captained by an expert, meaning all you have to do is show up and get ready to reel in some big catches!

We recommend booking with Aqua Excursions, a highly regarded provider of fishing charters that’ll take you through the waters surrounding Hilton Head. South Carolina fishing licenses are included and accommodations can be made for guests of any age. Book a charter anywhere from 2 to 4 hours long, and with different focuses that include seasonal fish, oysters, and even sharks!

Hold a Sandcastle Building Contest

Hilton Head Island’s beaches are pristine and wide—especially at low tide. The best way to keep kiddos entertained (and for you to easily keep track of them) is to hold a sandcastle-building contest. Whether it’s between just your group, or you’d like to invite your beach neighbors to the left and right of you, it’s a great way to spend an hour or two basking in the sunshine and enjoying some friendly competition.

What’s the prize going to be? Ice cream cone from the Frozen Moo? New beach toy from Hilton Head Toys? The decision of where your next vacation is? Make the stakes as high as you’d like! Speaking of height, make sure to knock those sandcastles down and fill those moats in. We don’t want anyone to trip, or any sea turtle to get stuck!

Four-seater street-legal golf cart

Rent a Golf Cart from Wheelz of Hilton Head

As fun (and practical) as riding bikes on the island can be, sometimes it’s just not feasible for your group. Or, maybe you want to shake things up for your next trip! Regardless of your reasoning, renting a street-legal golf cart from your friends at Wheelz of Hilton Head never disappoints!

It’s unique, it’s fun, and it’s easy to get around the south end of the island with a cart that has all the bells and whistles. Connect your phone to the Bluetooth speaker and sing along to your favorite tunes. Easily stow away your beach gear or groceries with convenient storage space. Have a bigger group? Reserve a six-seater! To learn more about how to book, who can drive, and where you can go, visit Wheelz of Hilton Head’s website.

Go Line Dancing

Yes, there’s line dancing on Hilton Head Island! A little-known fact that country fans love to find out, the Rooftop Bar at Poseidon in Shelter Cove Towne Centre hosts Coastal Country Night every Wednesday night from 7:30-9pm. Head there a little early, since there are complimentary line dancing lessons that start at 7pm. The night doesn’t end at 9pm, since the DJ Dance Party with the Top 40s starts at 10pm.

Always make sure to check the calendar before attending, since there’s a small chance that there’ll be a private event taking place. Additionally, the Rooftop also offers other specialty events like The Dueling Pianos Show every Thursday at 7pm, performances by local and visiting artists, as well as holiday parties that you won’t want to miss!

Photo by Hilton Head Helicopter Tours

Take a Helicopter Tour

How many people can say they’ve gone on a helicopter ride? Your kids will have the best answers to the question, “What did you do over break?” And there’s also a chance that they won’t stop talking about it, just a fair warning.

Hilton Head Helicopter Tours offers nine tours, with each one being unique and sure to fit your group and budget. A great activity for all ages, tours range from an 8-mile loop of the north end to covering the 12 miles of the island’s beautiful beaches, to a whopping 50 miles that takes you to see various lighthouses in the area or to a remote sea island populated by a colony of over 3,000 rhesus monkeys. Yes, monkeys. If monkeys aren’t your jam, you can choose other tours that allow you to see sharks, dolphins, and other marine life from a bird’s eye view, along with a deserted lighthouse, shipwrecks, and more!

Catch a Dinner Show

Two venues come to mind when we say “Dinner Show,” but there are certainly many other restaurants that host live entertainment almost every night of the week. The Comedy Magic Cabaret is a popular nighttime activity that provides quality, funny not filthy entertainment. Set in a smaller venue, reservations are recommended, but not required. Their menu is full of delicious snacks to share and sweet treats to enjoy. See the menu and check the schedule on Comedy Magic Cabaret’s website.

The second venue, The Jazz Corner, is an island institution and world-renowned jazz supper club. The menu is almost as impressive as the live entertainment, with starters ranging from lobster tails to South Carolina Peach Baked Brie, and a robust list of soups, salads, main courses, and of course, desserts. Now, the good stuff: the entertainment. You’ll be able to see who will be performing on the venue’s website, allowing you to make reservations for either show before they sell out—because they will. Because it’s so well known, not only does The Jazz Corner host local artists, but singers and groups from far and wide.

Adobe Stock

Go on a Cruise

Dolphin, sunset, dinner, lunch, firework, pirate, mermaid, holiday—boy, are there a lot of different cruises to pick from. Well, there sure is a lot of water in the Lowcountry, so it makes sense that there needs to be enough opportunities for everyone to get out and enjoy it!

Vagabond Cruise is a great start to finding the perfect cruise for your family or group. Sailing out of Harbour Town Yacht Basin, visitors have the chance to not only book scenic cruises but also convenient transportation to nearby Daufuskie Island and Downtown Savannah. In addition to the normal, climate-controlled vessels that run most of the cruises, Vagabond also offers opportunities to venture out on the 12-meter sailing yacht, the Stars and Stripes. This group is also known for its dinner and lunch cruises, which are such a unique experience for your friends and family.

Take a Family Picture

Last but not least, make sure to take a family photo. This may sound like a no-brainer, but sometimes we all have so much fun on vacation that it slips our minds. Make a point to gather as a group and don’t be shy to ask a fellow visitor or a local to take your picture. Don’t leave Mom to be the trip’s photographer, either. She wants to open up the photo album or social media page and see herself living those precious memories, too.

There are many places to take a wonderful photo good enough to make a Christmas card, but we’ve thought up a few places in particular:

  • In front of the Harbour Town Lighthouse,
  • At the top of the Harbour Town Lighthouse,
  • The swings at Coligny Beach,
  • Shelter Cove Marina,
  • On one of those fabulous cruises we previously mentioned,
  • On your bike or golf cart,
  • You can never go wrong with a picture on the beach!

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