We decided to take a family trip to Hilton Head Island, and even though I’ve been traveling here for years it’s my first time taking our toddler here. For me it was both very exciting and nostalgic to be able to experience all the fun things through the eyes of a toddler.

What to do?

Felix walking toward the gentle waves at Sea Pines Beach

There are 3 main things to do in Hilton Head with your toddler, the beach, the playground, and Harbour Town.

The Beach in Sea Pines is wonderful, the sand is soft, the water is warm, and the waves are gentle enough to enjoy them. We spent a majority of our days at the beach, we packed a lunch, played in the sand, the water, and even went for walks on the beach. This is the main attraction to coming to the island and it did not disappoint.

Slides and climbing equipment beneath the trees at Gregg Russell Harbour Town Playground

There are 2 main playgrounds worth visiting in Hilton Head, the Gregg Russell Harbour Town Playground, and adventure playground with the giant ship. The Harbour Town playground is a staple playground and has been there for years, I remember playing on the same equipment and trees when I was younger. I will say the adventure playground with the giant ship is geared more towards 7 year olds and above. Our toddler did seem to enjoy it you could tell he was struggling with how to use some of the equipment and the ropes.

Giant wooden pirate ship at the adventure playground in Hilton Head

Harbour Town lighthouse and boats at sunset on Hilton Head Island

Harbour Town at night is so magical, there is live music, tons of people on the classic red rocking chairs and the lighthouse and boats lighting up the sky. It was just a relaxed, friendly and safe place to be at night. My toddler had a great time and of course we had to get ice cream at the famous cinnamon bear shop. (On the back of Harbour Town shops with a giant bear in front)

Sailboat silhouetted against an orange sunset at Harbour Town

Getting Around the island

Hilton Head island is definitely a location you need a car for. Unlike London, Hilton Head doesn’t have public transportation. We stayed about a 15 minute walk to Harbour Town, 10 minute walk to the pool, and 30 minute walk to the beach. Since we live in NYC we are no stranger to walking places, but the places you couldn’t walk to was the grocery stores. That required a car. I did pack my travel stroller, the Zoe, but it wasn’t ideal for the beach, if you are looking for a beach stroller, I definitely recommend a wagon. For older kids, I definitely recommend renting a bike.

Where to Eat?

Lunch on the outdoor terrace at Sea Pines Beach Club Coast Restaurant

The good news is most restaurants are very family friendly and are used to accommodating children. We always did an early dinner when it was less crowded. There were so many amazing restaurants we wanted to try, but ended up cooking alot of the meals at our condo. We did however go to the The Crazy Crab (Definitely make a reservation beforehand, it gets really crowded). Our toddler loved the crab legs and the shrimp boil. I noticed tons of kids there. We also at Truffles restaurant twice, once for lunch and once for dinner. Not as many kids here, but the food was so good we went back twice, it’s a good blend between seafood and seafood alternative dishes. We did go to the Sea Pines Beach Club Coast Restaurant for lunch one day and while the service was outstanding, the food was just mediocre in my opinion. You definitely go here for the vibes since you are right on the water. This location is very kid friendly Finally my husband and I enjoyed the QuarterDeck as a datenight, since we only went here for drinks, I can’t comment on the food but loved the Hugo Spritz here. I did see a bunch of kids here.

If you are looking for a toddler / kid friendly place to go on vacation definitely add Hilton Head Island to your list. They even have an airport you can fly directly into, if you don’t have that option you can fly into Savannah and then it’s about an hour car ride from the airport to the island. I’d love to hear in the comments if you’ve been to Hilton Head island?

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