This is a long post describing my love affair with Hilton Head Island in South Carolina. I’m going to go over how we came to visit the area, and some of the things we did after spending multiple extended stays there as a family. I’m sure there is a lot of stuff we missed but I did a lot of travel planning and we have done a lot during our visits, so I feel I have a decent amount of information to share that might be helpful if you are planning a trip to Hilton Head Island.

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Why Hilton Head?

It all started during Covid-19. My husband has always worked remotely and my job was remote at the time. We took extra precautions because we had a newborn and were home a lot. In addition to having an active toddler, we were getting a little stir-crazy during winter.

I was cautious about travel. But, I asked if we could rent a cabin close to home just to get out of the house. He responded, “Why don’t we go somewhere warm for a month?”

I’ve never expected him to pitch an extended idea like that. But, we were just sitting at home, so to be able to hang out somewhere warm where our kids could play outside and we could work remotely was a nice version of snowbirding for us. Before he changed his mind, I set out to book something very quickly.

When it came to deciding on a place to go, I decided I wanted something within one day’s drive from us in southwestern PA. We did not want to fly because of Covid-19 and costs.

While I am certainly the beach bum type, my husband is not. And with going in winter, I didn’t anticipate too much beach time. So I leaned toward trying to find a beach as far south as I was willing to drive in one day that seemed to offer other things to do.

A lot of people in the Pittsburgh area vacation in Hilton Head, so I asked a friend why his family always goes to Hilton Head. He told me they love the beach and that you can ride your bike everywhere. I had no idea it was bike-friendly. So when I heard that, I was instantly sold.

Trip Planning

Here are a few things I did that helped me plan our trips to Hilton Head:

  • Before we went to Hilton Head for the first time, I wanted to learn more about the island and I found it helpful to request a vacation planner be sent to our home before our trip from the hiltonhead.org website.
  • I discovered a very helpful magazine that I referenced frequently called 101 Things to Do in Hilton Head. I later learned it’s available online if you want to plan ahead of your trip.
  • Lastly, I found it helpful to stop at one of the multiple available visitor centers upon arrival. I collected some helpful printed materials and the staff was friendly and helpful. Additionally, many restaurants have printed materials available too if you keep an eye out.

Preliminary Info

Here is some basic information I learned right away that I did not know about when I booked our first trip here on a whim. Of note, all of our trips have been in the off-season during the winter.

  • Bike-friendly – Starting with what I believe is my favorite feature, the island has 60+ miles of walking/biking trails. You can also bike ON the beach. While we take our bikes, there are several bike rental options on the island (many of which offer bike trailers and/or bike seat rentals for kids –Island Life Rentals and Hilton Head Outfitters to name a few). Visit this website more for info about biking in Hilton Head.
  • Plantations – Parts of the island are organized by plantations. When I plan a trip, I often study a place on Google Maps. So it’s not the kind of place where you just take a straight path to the beach. Many of the plantations are private communities.
  • Beautiful beaches – I’m not sure if it’s considered beach or beaches but I love the beach at Hilton Head. The beach is flat and wide with nice packed sand for biking and walking as previously mentioned. I don’t know if it’s the time of year we have gone, or if we have just gotten lucky, but the waves have been fairly calm. When the tide is out, I love the tide pools my kids could play in.
  • Built into nature – You can tell that nature conservation and preservation are a priority here. The island very much feels built into nature. Even the signage seems to have standards that feel like an extension of the landscape, so much so that it can even seem hard to find things. I had never seen a huge live oak tree with Spanish moss, so I was amazed at how beautiful the natural setting is here and continues to be with every visit.
  • Wildlife viewing – In addition to things you might see at the ocean like dolphins, pelicans, crabs, etc. the island has a lot of marshy or lagoon areas that offer other wildlife viewing opportunities such as alligators, turtles, a wide variety of birds, and more. There’s a good chance you’ll spot alligators. Remember to keep your distance and never feed the wildlife.
  • Food scene – There’s a big food scene that I love with lots of cuisines, various atmospheres, lots of outdoor seating opportunities, and more. I’ll dig deeper into this a little later in the post.
  • Parks – We spent a lot of time at parks and playgrounds and there are some beautiful facilities on the island.
  • Educational opportunities – There is so much to explore in terms of history, culture, nature, etc.
  • Day trips – We found a ton of day trip opportunities within 1-2 hours of Hilton Head.

Lodging

We have primarily booked condos through Airbnb. Some friends of ours suggested we stay in Palmetto Dunes which we did our first year. We liked it, but I think we enjoyed staying in Shipyard more which we did the following two years primarily because of the location. We like to bike as much as possible and we frequented Coligny Beach, and the businesses along Pope Ave including the Catholic Church and the Lowcountry Celebration Park, so I appreciated that Shipyard has an exit on Pope Ave. But if you stay in Palmetto Dunes, for example, you can still bike to that area (just a longer ride on the bike trails or bike the the beach there).

If you look into staying in Shipyard, there is a public beach access near the Sonesta Resort where many of the residents go to access the beach. With that said, I think our favorite lodging option so far has been when we stayed in Beachwalk in Shipyard. We were close to the beach access and then about a two-mile bike ride to our favorite places along Pope Ave. Where should we stay next?

Things to Do on Hilton Head with Kids

I’m going to discuss some of the things we did as a family on the island. Some of the activities are geared toward kids but there are a lot that are great activities for everyone, not just kid-focused. But let’s start with kid-focused.

Kid-Focused Activities

  • Pirates of Hilton Head – One year we tried what seemed to be a pretty popular kid attraction Pirates of Hilton Head where the kids felt like real pirates on a pirate family cruise. It was a lot of fun.
  • Lawton Stables – We enjoyed feeding animals at Lawton Stables. We didn’t get a chance to check out pony rides or horseback riding there, but that is also available. Just an FYI this is located on Sea Pines and if you aren’t staying there, there is a cash fee required for a day pass.

Another place we might want to check out next time for kids is Indy Karting & Amusement.

Harbour Town

A trip to Harbour Town makes for a nice day trip (again a Sea Pines day pass is required here). Here’s what we typically do – park near the beautiful Greg Russell Playground where the kids love to play, grab a coffee at Harbour Town Bakery & Cafe, walk down to the lighthouse, and enjoy the views of the boats in the marina. For a few dollars, you can walk up the stairs to the top of the lighthouse for a stunning view and take in some pictures and history on the inside. There are some places to grab a bite and shops to visit. This is where you can also consider climbing aboard Pirates of Hilton Head or perhaps a dolphin-viewing cruise. Check here for more ideas to explore Harbour Town.

Shelter Cove

Shelter Cove is a nice area to visit that offers a marina, shops, restaurants, a park with a playground, and more. It’s also a nice place to catch a sunset. Tip – it might feel intimidating to bike there because it’s set on the far side of William Hilton Parkway, but the bike trail goes under the busy road fairly (close to the entrance to Palmetto Dunes) which offers a more accessible experience via bike. I love The French Bakery and our family loves to pair a playground visit with ice cream at Kilwins.

Additional Parks and Playgrounds

Lowcountry Celebration Park is a must-stop if you have kids. This park is one of the most impressive parks I’ve ever taken my kids to anywhere and we spent a lot of time there. The park has an incredible pirate ship playground, adult swings, outdoor fitness equipment, a boardwalk for wildlife viewing opportunities, and more. In the warmer months, there are water/spray features in the playground.

We also enjoy visiting Chaplin Community Park which offers a playground, basketball courts, tennis courts, and more.

Jarvis Creek Park is another lovely park. There’s a walking loop around a lake, wildlife viewing opportunities, nice playgrounds, outdoor fitness equipment, and more.

Here are a few other playground or play areas worth mentioning that we enjoyed as parents who might want to have a beer while the kids play or run around. The Omni Hilton Head has a playground area and fire pits. Skull Creek Dockside is a nice waterfront restaurant we typically visit because the food and atmosphere are great and there’s a pirate ship playground with yard games. If I recall correctly, I think it’s also a nice place to catch a sunset. The Bank beer garden (with Side Hustle Brewing Co.) also has a large area where the kids can run around with a few yard games.

Points of Interest

Here are some other places of interest we enjoyed visiting:

  • Coastal Discovery Museum – Learning exhibits, kid’s zone, art, beautiful grounds and gardens, and more. Plus it’s free!
  • Historic Mitchelville Freedom Park – the first self-governed town of formerly enslaved people in the United States. This is one of my favorite spots on the island. I believe the park is still in the works, but even in its simple form, the self-guided tour brought me to tears.

Some other places I’d like to check out eventually are The Gullah Museum of Hilton Head Island, Sea Pines Foret Preserve, and Audubon Newhall Nature Preserve.

Sea Shelling

During our time on the beach near a lot of the vacation rentals for example the beach near Coligny, Shipyard, Palmetto Dunes, etc. I noticed there weren’t many sea shells. But, we found more shells in other areas. Here are a few suggestions for where to go sea shelling on the island.

  • Harbour Town Lighthouse – I’m not sure if it’s always the case, but last time we visited the shells were decent on the beach near the lighthouse at Harbour Town.
  • Pinckney Island National Wildlife Refuge – I don’t know if this is always the case, but White Point was the best sea shelling spot we found. We parked and rode our bikes there on some bike trails that were not paved and bumpy at times. I don’t recall the distance but I want to say it was at least 2-4 miles one way.

Other Recreation Opportunities

There are plenty of wonderful golf courses around. We have only golfed at Shipyard Golf Club which was great.

Some other recreation opportunities we observed include pickleball, tennis, kayaking, jet skiing, fishing, and again biking.

Church

We are a catholic family and we loved Holy Family Catholic Church for the central location that we often biked to, its welcoming atmosphere, extensive adoration hours we stopped in from time to time, and outdoor stations of the cross which we visited during Lent at a time my kids had a hard time behaving through the service.

Food

There is a large food scene here and we probably didn’t even scratch the surface but here are some places we liked and some we wanted to get to. Taste of Hilton Head magazine is available online if you want to start perusing food options. Here are some of our favorites we found:

Here are places we would like to check out but haven’t made it to yet:

Day Trips off the Island

We like to take day trips and we found a ton of places to explore near Hilton Head. Here are the places we went and what we did.

  • Bluffton, SC – (10-30 min from Hilton Head depending on where you stay) Bluffton is an adorable town where we just parked and strolled the town admiring the cute homes and downtown shops and also allowing the kids to play at Dubois Park. A great time to visit Bluffton is on Thursdays to catch the Bluffton Farmers Market. There are a few more details in a separate post, Day Trip to Bluffton with Kids.
  • Hunting Island State Park, SC – (about 1 hour from Hilton Head) On the way to Hunting Island, we stopped and visited Penn Center on St. Helena Island, part of the Reconstruction Era National Historic Park. This is the campus of the former Penn School, the first school in the South for formerly enslaved West Africans. We visited Hunting Island, we parked near the historic Hunting Island lighthouse. We walked around that area and were able to stroll to the beach and we found a playground nearby for the kids. We also visited the Hunting Island Nature Center. On the way home, we enjoyed a stop at Lowcountry Cider Company and Superior Coffee.
  • Charleston, SC – (about 2 hours from Hilton Head) – During our trip to Charleston, we parked and started our day at the South Carolina Aquarium. We decided to walk toward King St to stroll the shops and have lunch. Then, we walked to Marion Square for the Charleston Farmers Market.
  • Bucketlist – Some other places I want to go are Daufuskie Island and Parris Island, among others.

I hope you found this guide helpful for plans you may be cooking up for Hilton Head. If you have things to share please do. If you go to Hilton Head, please tag me on Instagram (@adventureswkelly).

Other Travel Itineraies

If you found this helpful, check out some of my other travel guides and itineraries (to list a few):