One of my family’s favorite places to vacation is Hilton Head, South Carolina. On our first trip there, I remember on the very first night my husband said over dinner that he felt like he belonged there (and he doesn’t get overly excited about things). It definitely does feel like a special place. I especially love going there because my Papa’s dream was to retire in South Carolina, and he did make that dream come true before he passed. He didn’t live too far from where we vacation now. It makes me feel close to him being down there, especially when we are getting ice cream with the kids (which is basically a nightly occurrence).
Another reason I look forward to this trip every year is that we go with dear friends of ours. They actually live right across the street from us, but we never get to spend as much time with them as we do on this trip due to the craziness of each family having two young kids (their daughters are the same ages as ours, so it is so much fun to see them growing up together). I feel like traveling with friends brings you so much closer because you get to experience new things together. Our kids obviously have so much fun too since they have friends to play with the entire time.
We always fly down for this trip. We have flown into Hilton Head’s airport once which is nice if you can find a good price, but we typically fly into Savannah. It’s only about an hour's drive from the airport to the island so I really don’t mind it. It’s also easier to get a rental car in Savannah because there’s a much larger inventory. My kids love this airport because there is an amazing candy shop that we always stop at before our flight back home. I like it because that’s where we would fly in to visit my grandpa, so it’s a nice memory when we arrive. It is also just a gorgeous airport, definitely one of my favorites in the country. They even have rocking chairs throughout the terminal that you can relax in while you wait for your flight.
Once we pick up our rental car, we head to our vacation rental for the week. Hilton Head is divided into 11 different “plantations” which are individual gated communities. The most popular ones are Sea Pines and Palmetto Dunes. During our first trip, we stayed in an amazing townhouse in Sea Pines in the main area called Harbour Town.
We absolutely loved staying here because of the gorgeous view of Calibogue Sound and the beautiful oak tree on the property. We could see dolphins swimming right in our backyard in the mornings, it was amazing. We were also right in the center of all of the fun things to do in Sea Pines so we could walk to all of the fun restaurants on the harbor and have dinner and hear live music. There is also the most adorable playground and a delicious ice cream shop right across the street. It is an absolutely perfect location for families.
The only downside to this rental was having to drive to the beach club every day. Sea Pines Beach Club is incredible. It has awesome food and drinks and fun things like popsicles for the kids. It’s important to have your beach chairs set up near a bathroom with young kids, so this was the perfect place for us to be. We would have our chairs and umbrella reserved through the lifeguards each day which made life so easy. However, parking at the beach club is extremely limited to non-members. We got lucky most days (it is advised you get there right when they open) but one of the days we had to park at a lot and take a trolley over. It was not a big deal, but with little kids and tons of beach gear, it was a little bit inconvenient.
The next year we decided to try something new and stayed in Palmetto Dunes. For this trip, we stayed in a condo that was right on the beach. This was super convenient with little ones because we had a pool and direct beach access. I liked exploring Palmetto Dunes, especially Shelter Cove which had fun restaurants, an ice cream shop, and unique shops. Something we added to this trip was renting bikes which was so much fun. The weather was a little bit cooler and my youngest daughter was not loving the beach, so we decided this would be a fun activity to try and they absolutely loved it. They had a little “kiddie-kart” we pulled them in and we made the best memories just biking around the island. I am definitely looking forward to making this a tradition on future trips.
Palmetto Dunes was a lot of fun and a different experience that I’m happy we got to check out. We did decide that Sea Pines felt more like the vibe we were going for, so we will be heading back there this year. We are going to try and find the best of both worlds by staying in a house in Sea Pines near the beach/beach club and also within biking distance from Harbour Town. Stay tuned for a future blog post on that trip!
Besides beautiful days at the beach, biking around the island, exploring playgrounds, and lots of ice cream trips, another highlight of this trip is going out to dinner! Coast at Sea Pines Beach Club is an oceanfront restaurant with amazing food and a one-of-a-kind experience. I think this is a perfect first night of vacation restaurant so that you can dine while enjoying a view of the ocean after a long day of traveling with a frozen drink and a wonderful seafood dinner. It is kid friendly and also has live music in the evenings. This definitely checks all of the boxes for us!
I think it’s unanimous that everyone’s favorite restaurant in Hilton Head is The Salty Dog Cafe. This restaurant has such a fun atmosphere but be sure to get there early during busy seasons to avoid hours-long wait times. Even if there is a wait, there is a beautiful pier to walk down, live music, and an outdoor bar to keep you occupied. The food here is great, like causal bar food but stepped up a notch with great seafood (I love their burgers!). They also have an iconic souvenir store where you must purchase a Salty Dog sweatshirt and an ice cream shop to top it all off. This is definitely a must-see Hilton Head destination.
My personal favorite restaurant on the island is Skull Creek Dockside. The views are beautiful as it is right on the water and there is a beautiful pier to check out before or after dinner. The menu here is amazing with almost too much to choose from. Whether you are in the mood for seafood, barbecue, steak, pizza, or pasta, you will surely find the perfect dish. Skull Creek also has a fun playground for the kids that we always visit after dinner. Skull Creek Boathouse is the sister restaurant on the other side of the playground that has a more seafood-focused menu including sushi. I always want to check it out, but Dockside is hard to pass up! This would definitely be a great area to check out on multiple nights of your trip to experience both restaurants. Hudson’s Seafood on the Docks is also in this location, so you can’t go wrong visiting this area for dinner. This restaurant is a really cool experience with fresh-caught seafood, just take the extra time to wait for an outside table because the inside is not nearly the same vibe as being out on the docks.
Another area where we like to dine is in Harbour Town. I think my favorite restaurant menu here is The Crazy Crab, but my favorite ambiance is Harbourside. You can see the boats and the lighthouse from this outdoor restaurant and they always have great live music. It is a really cool experience. This is actually the restaurant where my husband fell in love with Hilton Head on our very first night. If you sit outside at the Crazy Crab, you are actually still right across from the music of Harbourside, so it’s kind of the best of both worlds. This year, I am really excited to try The Quarterdeck. The first year we were there, it was closed for remodeling. We tried to go there last year but we didn’t realize it was Prom night for the locals, so it was a little bit crazy trying to eat anywhere. I have heard it’s one of the best restaurants in Hilton Head though, so I am really excited to check it out this year. After dining in Harbour Town, definitely check out The Liberty Oak which is a perfect photo op with the lighthouse in the background. There are also so many great boutique shops in this area perfect for souvenir shopping. We always end our night here with a trip to the amazing playground and The Cinnamon Bear Country Store for ice cream.
If you are looking for a family vacation filled with wholesome memories that will last a lifetime, I definitely recommend Hilton Head. The environment is so beautiful and full of southern charm, you almost feel like you are a character in a novel. From the gorgeous oak trees to the beautiful beaches, you will never run out of things to see and do. The restaurants are amazing, the people are so welcoming, there is amazing shopping, world-class golf courses, fun activities for kids… what more could you ask for?! Once you visit, you will surely agree that this is a truly magical place that will stay in your heart forever.
