Every family has their place. Hilton Head Island, South Carolina is ours. My first visit to the island was way back in 1987, soon after my grandparents moved south from Wisconsin. We made the day-long pilgrimage to Hilton Head from my small town in Southern Indiana multiple times a year. These treks continued until I was about 16, when my grandfather moved to Georgia after my grandmother passed. I didn’t return to Hilton Head until my college years, but it felt like I was coming home the minute we drove over the bridge.
Chris and I took our first trip to Hilton Head in May 2006, shortly after his college graduation. It was the first adventure we had ever taken, just the two of us. The photos of that visit never fail to bring a smile to my face. I remember walking down the pier in Harbour Town, watching the pelicans and feeling very much at home with this boy I loved so much.
For the better part of the last decade, we have spent the week between Christmas and New Year’s enjoying the island’s salty, piney air. Introducing our own children to the island has been such a joy. I haven’t spent much time in the Lowcountry in the summer since I was young, so I will put that as a point of reference. My aunt and uncle now have a home on the island and she has opened our eyes to many wonderful new places to eat and visit! (Thanks Aunt Maggie!)
The recommendations you find below come from years visiting HHI. Some of these spots are old favorites; others are new discoveries. I’ll fess up that we really take it easy with the kiddos — and spend many afternoons on long stroller walks (be it on the beaches or the paths around Sea Pines). I will continue to update this post after future visits to make sure we capture the newest additions. Be prepared… this turned into a serious novel. I warned you…
- Salty Dog Cafe (232 South Sea Pines Drive): It wouldn’t be a visit to Hilton Head without a stop at the Salty Dog. (You’re probably familiar with their t-shirts, even if you haven’t visited Hilton Head before.) I tend to eat a ton of shrimp when I’m in HHI, but I can’t leave the island without an order of their Buffalo Shrimp. We tend to make this a lunch stop, taking turns to run around with the little ones. They accommodate larger parties well, but you should definitely pack your patience for getting a table.
- Holy Tequila (33 Office Park Road, Suite 228): If you’re staying in Sea Pines, Holy Tequila is just off plantation — making it a convenient and delicious destination. They make large parties feel welcome and kids aren’t frowned upon either. I appreciate the frequent live music — and copious amounts of chips provided. They have a wide selection of creative tacos, making it great for all tastes.
- Fishcamp on Broad Creek (11 Simmons Road): If you’re looking for a spot to camp out, Fishcamp is it. Kids — and adults — can entertain themselves with yard games. Their Bloody Marys are also absolutely epic. We have loved this spot for large parties, especially at brunch time.
- Hudson’s Seafood House on the Docks (1 Hudson Road): My grandparents lived in Hilton Head Plantation, which is very close to Hudson’s. It became a family favorite many moons ago. The view can’t be beat and it is a great spot to visit when you first arrive on the island! Large tables are doable here.
COFFEE + MORE
- Harbour Town Bakery & Café (140 Lighthouse Road): For the last three visits to HHI, we have stayed in Harbour Town. It took me a few days to figure out where people were getting their morning coffee… until I looked across the parking lot to an inconspicuous cottage. This tiny café is great for a quick stop — or a full breakfast. (It is where we discovered Rosie and James loved waffles!)
- Java Burrito (1000 William Hilton Parkway, Suite J-6): When we need a pick-me-up while shopping in the Village at Wexford, this is the spot! I know many people love it for their food, I can only attest to the coffee. It’s cozy and local — two things I love in coffee shops.
- Starbucks (11 Palmetto Bay Road, Suite 108): If you need a classic cup of coffee — or in my case, a cold foam cold brew — you can find it here. We often make our way here after a ride at CYCLEBAR Hilton Head. I knew I couldn’t make a reference to coffee without including a Starbucks. I like to try new spots when we travel, but it’s sometimes nice to know where the familiar cups can be found. (Note: I believe there is another location opening in Shelter Cove in the coming months. You can also find a small location in the Harris Teeter we frequent, outside of the front gates at Sea Pines.)
- Lowcountry Produce (The Shops at Sea Pines Center: 71-510 Lighthouse Road): A short walk — read 10-15 minutes — from Harbour Town, we loved hopping over to Low Country Produce when our kiddos used to take morning naps in the stroller. We first visited their location in Beaufort in 2013 and fell in love with its charm. They have tasty coffee and juice selections, as well as the ability to take a seat for breakfast. Our kids normally don’t have the patience, but I look longingly at the delicious breakfasts when we make our quick stops.
- The Crazy Crab (Harbour Town: 149 Lighthouse Road + on the drive on island: 104 William Hilton Parkway): There is a lot of charm in the Harbour Town location, but I love the setup at the one as you drive on island. I will admit that I dream of their hush puppies — when I’m eating mediocre ones in New England 😉 My late grandmother adored their key lime pie; she would always order a piece to go (a tradition I have proudly continued).
- Giuseppi’s Pizza & Pasta House (50 Shelter Cove Lane): Truth be told, I haven’t been here in years — but their calzones are etched into my brain. If you want a classic pizza joint, Giuseppi’s is your winner!
- Skull Creek Boathouse (397 Squire Pope Road): I know many people adore Skull Creek, but somehow, we never end up there — but in the times I’ve been, it is always packed and delicious!
- Old Oyster Factory (101 Marshland Road): I have a few favorite family memories at the Old Oyster Factory, thanks in part to the gorgeous view and classic southern fare.
DATE NIGHT WINNERS
- Lucky Rooster Kitchen + Bar (841 William Hilton Parkway): This spot is tucked into a random strip mall, but I promise it is worth the trip. The dishes are creative and the ambiance is jovial. We have only been once (and tiny James was with us), so I list it as a date night spot because I don’t have much knowledge about how it would be when kids are more active.
- Ruby Lee’s South (19 Dunnagons Alley): Need some live music with solid food and atmosphere? Ruby Lee’s South is just the spot! My aunt introduced us and I’m so glad she did. I think it would be even more fun in the summer, when the windows and doors are open… we’ve only been in the winter when the weather can be hit or miss.
- Jane Bistro & Bar (24 Shelter Cove Lane): When you step inside Jane, you might forget for a minute than you’re in a beachy destination. I have been for both lunch and dinner fare — and neither disappointed. (For the record, I classified this as a date night spot because the menu is a bit more sophisticated than what my kids might enjoy.)
- Sea Pines Beach Club (87 North Sea Pines Drive): If you’re staying at a property in Sea Pines, you can take advantage of this beachside oasis. We have taken the kids here on occasion, but it has a wonderful bar that would be best enjoyed kid-free 😉
- The Sage Room (75 Pope Avenue): For a unique dining experience, The Sage Room fits the bill. We sat at the chef’s table and we were privy to seeing beautiful meals come to life… right in front of us!
- Frosty Frog Cafe (1 North Forest Beach Drive): This is most definitely an adult destination — with some fun memories from my early 20s. Most notably, there are (or there were?) takeaway bevies, in both cup and gallon form. If you like piña coladas, you’ll love the Frosty Frog.
- Gregg Russell Harbour Town Playground (140 Lighthouse Road): I have vivid memories of frolicking around this playground… when I was three. Seeing my kids play here gives me so much joy. We typically stay in a villa through Sea Pines in Harbour Town, so it makes it easy to roll here first thing in the morning. It is a fabulous playground for all ages, which is nice when you have kids at different agility levels. This playground is definitely one of the reasons we choose to stay close to Harbour Town each year.
- Pirate’s Cove (8 Marina Side Drive): Chris loves golf… and has shared that love with James. We mini-golf more than the normal family, I’ll give that caveat. Pirate’s Cove is equal parts cheesy and challenging. There are a number of other places to go on the island, but James really loves the pirates. What can I say?
- Bike & Kayak Rentals: Depending on where you end up staying, there are many different options for rentals. In our days before kids, we had a few very memorable jaunts around Palmetto Dunes in a kayak. I call them memorable because Chris likes to remind me how slow I was. You win some, you lose some 😉 This said, bikes are a staple in each of the plantations — and even for some jaunts off plantation. You can rent many different styles of bikes (tandem, with trailers, etc.), so you’ll be able to cover everyone!
- Dolphin Cruises: I haven’t been on a cruise since I was young, but I loved them… and am anxiously awaiting the day we can take James and Rose. You can often spot dolphins at the end of the pier near the Harbour Town lighthouse. (There are also some great picnic tables out there for fun lunches — either take-out or packed from your kitchenette!)
- Shelter Cove (19 Shelter Cove Lane): Little boutiques and big chains alike, there are SO MANY options for both shopping and food in Shelter Cove. (This is also where you’ll find the island’s Whole Foods!)
- Coligny Plaza (One North Forest Beach Drive): Coligny Plaza is the best place to find those quintessential swimsuit shops you find on vacation, but you can also find charming shops in its midst.
- Village at Wexford (1000 William Hilton Parkway): I remember going to shops in the Village when I was tiny… it has loads of charming boutiques and ample spots for food and coffee. These are a few of my favorites in the Village:
- S.M. Bradford Co. (Harbour Town: 149 Lighthouse Road | Village at Wexford: 1000 William Hilton Parkway): I don’t even want to share my secret, but I find some of Rosie’s best Lilly Pulitzer in the sale racks at S.M. Bradford. Our visits are often timed well with their semi-annual sales, but regardless, it is worth digging through their racks!
- Louette Boutique (Village at Wexford: 1000 William Hilton Parkway): Louette could best be described as if your favorite children’s store and Anthropologie had a baby. It carries children’s and women’s clothing items for all ages — as well as lovely little gifts to charm and delight the recipient.
- Island Child (Village at Wexford: 1000 William Hilton Parkway): If you could picture a classic Southern children’s store, it would be Island Child. (I definitely remember playing under their clothing racks as my mom would find dresses for special occasions throughout my childhood!)
- LowSea Rentals: I learned quickly that bringing all the baby items you need for a week is just not feasible. Especially when you’re attempting to create a home away from home, renting high chairs and jogging strollers makes life so much easier. We’ve used LowSea Rentals a few times: our order always arrives promptly and they’re very responsive. (I tend to remember as we’re on our way to the airport… maybe this year, I’ll be more on top of it!) FYI: The bed rails are also a nice quick add, to help everyone get restful nights of sleep once they’re out of cribs!
- Speaking of children, Guardian Angels Sitting Service is an incredible resource — if it’s needed.
- Since many folks visit the Island hoping to golf (with real clubs, not just a putter at mini-golf), I consulted our in-house golf expert. Chris has played Harbour Town and Atlantic Dunes in Sea Pines. He has also played Oyster Reef in Hilton Head Plantation, where my grandparents actually had a house on the 12th hole! He says the golf can’t be beat — and only suggests to plan in advance to get the best tee times, which should come as no surprise to most avid golfers.
- Most visits, we make a stop at the Target in Bluffton (1050 Fording Island Road, Bluffton, SC). We tend to grab the basics we need for a week to discourage us from eating every meal out of the house.
- Once we’re on island, I go to the trusty Harris Teeter near Sea Pines. My grandfather loved this chain during his years on Hilton Head — and I grew to love it during our long-distance years when Chris was in Charlotte. For New Englanders, you’ll also be delighted to know you can get beer and wine IN STORE.
- We typically fly into the Savannah airport and rent a car for the ride over to Hilton Head. The rental car facility is incredibly easy to access. You’re in your car (or van) in minutes. Pre-kids, we loved flying into the airport ON Hilton Head. It’s a bit more expensive and always requires a transfer… but it’s so nice to just be plopped into paradise!
- As for accommodations, I really think this is up to each family — depending on budget and desired location. We have come to truly love Sea Pines, which we didn’t visit much during my grandparents’ decade on the Island. I also enjoyed our time in Palmetto Dunes (we stayed at the Hilton Head Marriott, pre-kids). I also have fond memories staying at Disney’s Hilton Head Resort, but I haven’t stepped foot on that property since I was 12… so I can’t speak to it today. All of that said, we have had great luck renting a villa directly through Sea Pines. I cannot go without mentioning my aunt rents her properties on VRBO — and there are many beautiful options available there as well!
PHEW. I could never capture it all, but this was a solid attempt! If you have any other questions, I’m happy to field them… either leave a comment below or shoot me an email 🙂 Here’s to making new memories in Hilton Head — and beyond!