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Hilton Head: Our Go-To for a Relaxing Family Road Trip

Memorial Day weekend is a perfect time for our family to slip away. With the boys out of school for at least a three-day weekend (sometimes four, depending on snow days!), we can travel without them missing much, if any, school.

This year, we craved a relaxing, beachy destination with excellent food options. Hilton Head, South Carolina immediately came to mind as a fantastic weekend escape! This wasn’t our first visit, but we still had a wonderful time and are already looking forward to our next trip.

We’re excited to share some highlights from our adventure. For a more in-depth look and our full itinerary, be sure to join our newsletter!

Our Stay at Disney's Hilton Head Island Resort

We drove to Hilton Head, splitting the journey the evening before, so we could arrive around noon. For this trip, we stayed at Disney’s Hilton Head Island Resort, using our Disney Vacation Club (DVC) points, which meant no cost for the accommodation. We booked a two-bedroom unit and were thrilled to invite some longtime friends to join us.

We had requested a room near the pool, and while it wasn’t ready at noon, it was still early! We decided to grab some lunch, and our room was actually ready for us before 1 PM.

The resort itself is lovely. The main building, The Live Oak Lodge, houses some standard studio rooms. The lobby is incredibly inviting, reminiscent of an upscale cabin in the woods. We loved the charming, old-time key holder behind the front desk – a nostalgic touch, even though they no longer use physical keys. Across from the front desk is a cozy seating area with a hanging swing, couches, and lounge chairs. In the mornings, you can enjoy complimentary coffee here, and in the afternoons, there are delicious cookies.

The staff at Disney’s Hilton Head Resort were incredibly friendly and welcoming. They offered great restaurant recommendations, gave us a quick overview of the resort, and confirmed our pool-side room request. Our key cards were provided immediately, though not yet activated. A helpful tip for Disney resorts: key cards (and MagicBands) can be set up with charging privileges, which is very convenient, but something to note if you have kids! We opted not to enable charging for our children’s cards this time. The best part? Once our room was ready, we simply received a text with our room number and could head straight there without another stop at the front desk.

Navigating the Resort

The resort is a bit spread out, so it’s a good idea to glance at the map upon arrival. It features several buildings offering a variety of studio, one, two, and three-bedroom units. Our two-bedroom unit was in a building with a total of four two-bedroom units – two on the first floor and two on the second. This year, we had a first-floor room; last year, we were in the same building but on the second floor. I don’t have a strong preference between the floors, but it’s worth noting: on the first floor, you might hear people running or jumping above you. Second-floor rooms mean more stairs. While some buildings do have elevators, they aren’t common, and I wouldn’t count on elevator access unless specifically confirmed. If climbing stairs is an issue, definitely contact the resort before booking, as even first-floor rooms have a few steps to enter.

Soaking Up Some Sun: Pool & Beach Fun

Our trip was all about relaxation, meaning plenty of pool and beach time! We were incredibly lucky, as our room was right behind the main pool, offering a view and a very short walk. The main pool boasts a fun water slide that both our kids absolutely loved. It’s not massive, and we saw many smaller children enjoying it without a problem. The pool water was warm, and there was ample seating. Adjacent to the pool is another building housing an activity area, a resort store, and a small, window-service restaurant called Tide Me Over, serving breakfast and lunch. There was also a very small cart offering adult beverages. Important to note: there’s no on-site restaurant for dinner. Disney’s Hilton Head Resort is unique in that it doesn’t have direct beach access. However, they have a fantastic, separate Beach House just a short drive away, exclusively for resort guests (requiring your key card for access). If you didn’t drive, it’s no problem. The resort offers complimentary shuttle service that runs throughout the day. You simply get on right in front of the resort and the drop you off directly in front of the Beach House. At the Beach House, you’ll find a second pool, shaped like an “H,” and another window-service restaurant, Signals, offering essentially the same food and drink menu as Tide Me Over. Beach access is readily available from here. It’s a fairly quick walk over the sand dune, made even easier by a mat that extends across the dune, opening right onto the beach. Since we drove, we brought our own beach gear, including chairs, umbrellas, and, of course, beach toys. Our beach wagon was invaluable for lugging everything! If you didn’t drive or just didn’t want to pack all the beach gear, there are chairs and umbrellas available to rent. The Hilton Head beach itself is beautiful. The sand is quite packed in many areas, making it easier to walk on, and during our visit, the water was very shallow. At low tide, little tide pools formed, perfect for even small children, as the water is only a few inches deep and separated from the ocean because of the low tide. There weren’t many big waves, so the kids could swim and play without us needing to hold onto them constantly. The ocean water was also surprisingly warm. For added peace of mind, there’s a lifeguard on duty during the day.

Taste of Hilton Head: Where We Ate (and Loved!)

Hilton Head boasts some truly fantastic food options! As mentioned, the resort doesn’t offer on-site dinner, so you’ll definitely need to venture out for at least your evening meals – which is great, because there are amazing choices. While we couldn’t hit every awesome spot, we had some wonderful experiences and delicious food! We’ll give you a brief overview of where we ate here, but for much more detail, remember to check out our newsletter. We dined at Kenny B’s, Dockside, Hilton Head Social Bakery, Poseidon, The French Bakery, Smokehouse, and the two resort restaurants, Tide Me Over and Signals.

Kenny B’s is a unique spot specializing in Louisiana-style cuisine. Our youngest tried alligator for the first time and loved it (our oldest wouldn’t touch it!). The gumbo was excellent, and their beignets, dusted with tons of powdered sugar, were yummy – though they are definitely better when they are warm.
Dockside was a fun experience. Despite being told there would be a long wait, we snagged a couple of first-come, first-serve outdoor tables. Their petit filet mignon with lobster and cream sauce on top was incredible! The kids loved their shark head cups.
We’d visited Hilton Head Social Bakery before, and they never disappoint! This breakfast favorite is a short walk across the harbor. They specialize in pastries but also offer hot breakfast items. Our family’s favorite is the chocolate banana croissant, and the monkey cappuccino was a great choice too.
But the absolute best restaurant of this trip was The French Bakery. We’d seen it on a previous trip but couldn’t fit it in – it will now be a staple for all future visits! Between our family and our guests, we ordered their famous Quiche Lorraine, the incredibly rich Chocolate Decadents French Toast, Nutella Crepes, Bananas Foster Crepes, and (probably the star of the show) the fluffiest omelets we’ve ever seen! We even had to include a picture of these because they were just that good. Everything was delicious, and the Café Mocha had beautiful foam art on top.
For quick and casual dining, the resort restaurants serve their purpose. While not gourmet, we enjoyed the pimento cheese as a snack, and the Dole Whip was, of course, a refreshing treat! A key tip: these spots typically close for dinner, so be sure to make other arrangements for your evening meals.

Beyond the Beach with Some Disney Magic

We enjoyed beautiful weather for the most part, with daytime temperatures in the 80s. Unfortunately, Sunday brought rain. But the Disney crew had us completely taken care of! The kids headed to the activity area, where cast members brought out crafts galore! Our children made paintings, sand art, coloring pages, and trinket boxes – all for free! Other activities the kids enjoyed over the weekend included making Mickey wreaths (a paid activity, but remember your DVC member discount!), character meet-and-greets with Chip and Dale and Pluto. As a family, we participated in a sing-along and made s’mores on Saturday night. When you check in, the cast members provide a detailed schedule of weekly activities, so be sure to pick one up!

Shopping & Souvenirs

There’s some convenient shopping nearby if you’re interested. There’s a mall area with many stores within walking distance (though be mindful of traffic). You’ll also find some shops on the way to the Beach House. We only stopped at the general store, where we found plenty of touristy items and necessities in case you forgot anything. We also got to visit an art show that was happening during the weekend. There were some incredible vendors and we enjoyed browsing – and may have picked up a couple of fun souvenirs.

Our Verdict: We'll Be Back!

Overall, our Hilton Head trip was fantastic! Despite a little rain, the kids had a blast, and the adults got to relax, which, in our book, makes for a successful trip! This was our second visit to Hilton Head, and we will absolutely be back. Our only minor complaint was getting a bit eaten up by bugs in the evening, so that’s something to be aware of. However, the beach is wonderful, the hotel is great, there’s something to do for every age, and the food options are amazing. We definitely recommend Hilton Head for adults and kids of pretty much all ages! We hope this glimpse into our family weekend getaway has inspired your next trip to Hilton Head! Want to plan your own perfect escape? Our newsletter has all the extra details, including our complete day-by-day itinerary, to help you make it happen. Subscribe today!