hey, friend! welcome and thanks for shopping!

Our Hilton Head Vacation Recommendations

Written by Opalmaree Stone


Posted on April 04 2022


Call us crazy, but we did it again…road trippin’ with young kids across the country. And yet again it was worth it. So without further ado, here’s an overview, tips and our family friendly recommendations from our road trip with littles to Hilton Head Island, South Carolina. 


  • TIMING: Leave during a time that will allow you to get at least a few hours of driving in while the kiddos snooze. We have M (5), L  (2) and J (6 week old). We try to leave either before naptime or super early in the morning - like 3am-5am. Of the 6 or so legs we’ve done road tripping with our kids, this has worked for us!
  • STOPS: Be open to stopping whenever you need. It is SO important to be flexible on a road trip. We didn’t book any lodging for the route. Our plan was to go as long as we could. We stopped every 3-4 hours for diaper changes, feedings, snacks/meals or a walk.
    • Suggestions:

-Find a dollar store or Walmart on the route and the kids can pick out something to keep them entertained for another few hours or if you’re more organized wrap some “gifts” from the dollar store to pull out when you need a distraction and something new.

-Don’t wait until you NEED to fill up with gas in case the kids are sleeping during that time. Stop and fill up during a stop when everyone is already awake.

-You will likely get an idea of when you’ll be ready to stop the longer you are in the car. L (2) did not want to fall asleep in the evening in the car, we knew we only had probably an hour max left before she was going to NEED to go to bed. At this point, I started doing research on where to stop and hotel options.

  • PACKING (besides the obvious)

-One double stroller + one umbrella stroller 

-Baby Dome - this was PERFECT for J on the beach and by the pool. We also brought a boppy lounger that fits perfectly in it.

-Portable Sound Machine for J and plug in Sound Machine for L

-Beach and Pool Toys

-California Beach Blanket…borrowed this from a friend and purchased one for ourselves when we got home we loved it so much.

-Backpack Cooler

-Small Diaper/Pool Bag

-Pump + Breastmilk Storage Bags (click HERE for an amazing portable pump recommendation)

-Hot/Cold Tumblers

  • SNACKS: each child had a lunch bag full of snacks. Our favorites for the kids: prepackaged items such as scooby snacks, pb cracker sleeves, and fruit snacks. We also had string cheese, apples and juice boxes in each of their lunch boxes, and a water bottle. Our favorite snacks: gardettos, beef jerky, nuts, pb monster mix (linked because it’s the absolute best)
-Suggestion: Don’t forget a garbage bag and wipes in case things get messy.
  • ENTERTAINMENT: each child had a backpack with some activities, toys. M (5) had his switch, ipad (no data), a book, fidgets and maze book. L (2) had a drawing pad, coloring book and crayons, stuffed animal, book and fidgets. Click HERE for some W&P product recommendations. They also would get to play on our phones when necessary (we used our phones as a last resort because we didn’t want them to get sick of those and then we were left with no other “more exciting” options. We also had my Ipad with downloaded Netflix movies and shows.
-Podcast Recommendation: Up and Vanished  



    Marriott Vacation Barony Beach Club: 10/10 would recommend 

    -We had a two bedroom villa which was extremely roomy. We probably could have fit two families in there but it did work well for us because L slept in one room, M slept on the pullout couch and J was with us in our room. There was a full kitchen so we had at least one meal a day in our villa. Gorgeous bathrooms, very clean and we requested a garden view villa but ended up with a partial ocean view as well.

    -Beautiful grounds for walking - quick 2 minute walk to the beach which was private on the resort grounds.

     -Restaurant and Bar with a happy hour and daily specials as well - free caramel apples, mimosas, movie + popcorn

    -Lawn games and other outdoor games available to play



    -The beaches in HHI are gorgeous and very family friendly. If you are looking for a beach that kids can build sandcastles, splash around in the water safely and even STROLLER on the beach…look no further. Riding bikes on the beach is even possible and in fact, popular.

    -DOLPHINS - we saw dolphins almost every time we went to the beach. Although we didn’t go on any, it seemed like there were lots of options for dolphin watching tours and other similar adventures


    -When we were looking for accommodations we knew we needed to find a place with an outdoor HEATED pool and at least an indoor pool which was a little harder to find than one would think. Thankfully, Barony Beach Club had both. Two outdoor pools (one heated) and one indoor pool (also heated) with several hot tubs as well.  


    -Gregg Russell Harbour Town Playground: close to some shopping, the Harbour Town lighthouse (which was under construction when we went), Harbour Town Bakery and Cafe and Lawton Stables 

    -NOTE: You do need to pay an entrance fee to get into Harbour Town so it is better to plan maybe a half day here so you can get your money’s worth. 

    -Shelter Cove Community Park: we traveled during a time that was not as busy so there weren’t festivals or concerts but I think this is a location where during busier times there may be more hustle and bustle. This is a great location in case a parent wants to sneak away for some shopping while the other stays with the child(ren) at the park. I snuck away to do some shopping at Shelter Cove Plaza. 

    -My favorite shops in this area: Coastal Bliss, Island Sole, Island Trading Co

    -Celebration Adventure Playground: hands down, our kids’ favorite stop! This playground was so amazing and it seemed relatively new as well. It’s also right next to The Sandbox, an indoor children’s interactive museum. We did not got to the children’s museum but it does have very great reviews online - if there would have been a rainy day, we would have tried it out. 



    -Coligny Beach Plaza Shopping : another shopping area with a playground and our favorite stop was the Carolina Tasting Room. Grab a wine slushie or some wine and walk around and shop

    -Adventure Cove Mini Golf : there are LOTS of mini golf or regular golf options in Hilton Head

    -There are little shopping plazas all over Hilton Head - with three young kids it wasn’t the easiest thing to do. There are also a lot of larger department store and chain retailers than I expected. 



    Harbour Town Bakery and Cafe  : Great option for a latte and some bakery. We tried a blueberry scone and chocolate croissant and they did not disappoint. This is also right across the street from Gregg Russell Harbour Town Playground. 

    Skillets Cafe and Grill : Classic breakfast restaurant that was casual and had great customer service

    Duck Donuts : We waited until the last day to try this…MISTAKE. This is a franchise and apparently they are all over the country but not many in the midwest or certainly Wisconsin. Imagine mini donuts but large warm, made to order donuts with your choice in toppings. So delicious! 


    Street Meat : Quick, casual and had good reviews. Outdoor seating available and kids could walk around on the patio without being a distraction to others. Food was good, but pretty standard for a bar and grill type place. I had the fish fry which was hyped up on the menu, but believe it or not I think I preferred my Wisconsin Fish Fry more! ;) 

    Java Burrito : A local Chipotle like joint but a million times better! Literally the best burrito bowl and arguably tacos I’ve ever had. Plus a great margarita happy hour! Our family took down a large guac and the kids were big fans of the cheese quesadilla. Another stop we would have easily done twice if our trip was longer. MUST STOP.


    Skullcreek Boathouse : A must! Especially for families. They have a cute little playground that you can hit up while you wait for a table and the adults can grab a drink while the kids play ;) A big patio and delicious food. Kyle had been wanting to try a fish boil so he did that and wow, it was tasty! I had some seafood chowder and the kids shared a kid’s meal. And complimentary free sweet cornbread. 

    The Salty Dog : This one came highly recommended and it did not disappoint. Another casual atmosphere that is great for kids. There’s also some entertainment options for before or after dinner - gift shop and ice cream.


    We had an amazing time on Hilton Head Island. We’ve survived two 20+ hour in the car road trips now with young kiddos and as scary as it sounds, we have found them 100% worth it. Seeing our kids splash around in the ocean and nap to the sound of the waves are memories that are worth the handful of tantrums and stressful moments we had in the van. 

    Have you visited Hilton Head Island? If so, leave your recommendations below! 

    Click HERE for a little snapshot of our trip.

    Happy traveling, friends!



    Leave a Comment