My family and I just recently returned from our third annual trip to Hilton Head Island in South Carolina and it was as magical as ever. If you have never visited Hilton Head, it is divided up into eleven gated communities referred to as “plantations.” We have previously stayed at two of the most popular ones, Sea Pines and Palmetto Dunes. For our first trip, we stayed in an amazing townhouse in the Harbour Town area of Sea Pines (home of the famed PGA golf course Harbour Town Links). The following year, we stayed in an oceanfront condo in Palmetto Dunes. I wrote about both of these wonderful rentals in a previous blog post which you can check out here. This year, we returned to Sea Pines and stayed in a private home that was the second row from the beach. To be honest, I was not as excited about this rental as in previous years because I absolutely love to wake up and be able to see the ocean, but (spoiler alert) the private pool and immediate beach access ended up winning me over :)
Each year, we take this trip with our friends/neighbors and it is so special to watch our daughters grow up together summer after summer. The first year, it was just our respective three-year-olds and my 9-month-old. The following year, our friends had their new baby who was born one year apart from our baby. That made this the first trip where neither mom was pregnant or nursing, so it was a much more relaxing experience for us, and the little kids also had so much more fun playing together.
Traveling without the need for a high chair or crib is a whole new world! Although, I must say… we always rent through Sea Turtle Getaways and they offer services for basically anything you could ever need from baby gear to beach chairs to bicycles. We have rented cribs, high chairs, and even bins of toys (we did rent the toys this year too), as well as bikes with kiddie carts, which is an absolute must in Hilton Head. I highly recommend booking through Sea Turtle Getaways for your Hilton Head vacation.
When we first arrived at our rental, I was so impressed with the private pool. Our now five-year-olds absolutely love to swim, so this made the trip extra special for them this year. We had access to a pool with both of our previous rentals, but having our own did feel special and was very relaxing. We also had bikes with kiddie carts waiting for us when we arrived, along with our bins of toys, so we were able to just unpack and get right to the fun activities. We also used my hack of ordering groceries from Instacart on our drive from the airport, so we had a stocked refrigerator within an hour of arriving.
We did get to the island a little bit before our house was available, so we stopped at Harbourside in Sea Pines for waterfront food and drinks as our first stop. This is also next to the best playground, so the kids (and parents) were off to a good start! We actually ordered our favorite pizza from Giuseppe’s on our first night so we could get settled and get the girls to bed early to be fresh for their first full day. This was fine with us because they seriously have the best pizza ever!
For our beach days, we walked down a cute little path and had beach chairs and umbrellas set up right at the access point each day by Shore Beach Services. We always have the best experiences with their kind and helpful staff each year. Basically, all we had to do each day was show up and lay out our beach blanket and sand toys for the kids and we were set. We also packed coolers each day with drinks and snacks. We did rent beach wagons this year as well which were nice to have. Hilton Head has lots of jellyfish (which the locals always tell us are the kind that doesn’t sting) that wash up on the beach which the girls love to see. We also saw a starfish this year as well as schools of dolphins swimming by! After spending the mornings at the beach, we would head back to the house for the little ones to nap and the older girls loved swimming in the pool and eating popsicles. Those were some of my favorite moments just watching them have fun.
After naps for the girls and coffee time for the adults, we would ride our bikes around the island in the afternoons. Bike riding in Hilton Head is so peaceful with all of the majestic oak trees and diverse wildlife. On one bike ride, we saw the most beautiful crane, an alligator, and lizards. The girls absolutely loved riding around and looking for animals. After our adventures, we would go home and get ready for dinner.
My favorite restaurant we went to this year was The Quarterdeck. We were unable to go there the past two years because it was being remodeled the first year and the second year we happened to be there during prom and all of the restaurants were fully booked. This place was so nice and just felt like a special treat. It overlooks the Harbour Town Links golf course, which our husbands loved. They have the most beautiful outdoor balcony and live music as well as amazing food and drinks. This was definitely a highlight of our trip. We also went to our Go-To favorites including Skull Creek Dockside, The Crazy Crab, and The Salty Dog Cafe (of course). We also tried a new place this year, A Lowcountry Backyard Restaurant. We had heard great things about it and it was a really cute place with twinkle lights and live music. I tried shrimp and grits for the first time because it is said to be the “world’s best” and although I was a bit skeptical, I did love it!
Our evenings were spent at playgrounds and getting ice cream which is exactly where I wanted to be. I know that I will be sad when my kids outgrow this sweet innocent time of life when they want to spend all of their time with us. I just try to soak up every moment while we have it. We did discover an amazing new place this year, Adventure Playground. I would say it is possibly the coolest playground my kids have ever been to! Not only was the play area awesome, but the surrounding area was a water feature full of turtles and alligators which was really cool. There was also a great ice cream shop, The Ice Cream Cone, right across the street which had a huge menu to choose from. Most other nights we went to the Gregg Russell playground at Harbour Town and the Cinnamon Bear Country Store ice cream shop which are always our favorites. Plus there is so much great shopping in that area which is where we always get our souvenirs before heading home.
On our last day, we had breakfast at the Harbour Town Bakery & Cafe which was an amazing way to end the trip. We had pecan sticky buns under the oak trees in our Salty Dog t-shirts and then played at the playground and did a little souvenir shopping before heading to the airport. I am always so sad to leave this vacation because Hilton Head really has carved out a special place in our hearts. It is so special to have a place that my kids and my husband and I all love so equally, and having such awesome friends to share our experiences with makes it even more magical. I am already looking forward to next year. I think an oceanfront private home will be the perfect choice, so I will tell my husband to start saving now ;) I also would like to add a few new dining options to our itinerary for next year, so if you know of any must-try restaurants that we have missed, please leave a comment and let me know!
