Hilton Head Island, South Carolina — An All-American Family Vacation Without the Costly Price Tag & Crowds

Hilton-Head-family-vacationHilton Head Island, South Carolina — An All-American Family Vacation Without the Costly Price Tag & Crowds

by  Emily Edmonds

Hi, Williamsburg friends! I’m Emily, a fellow BFF of Tripbound’s Frugal Travel Mama and a busy working mom of two girls—Holly, age 8 and Ella, age 10. I’m currently holding down three jobs while trying to soak up every ounce of family time we can together before they grow up.

For that reason alone, I absolutely cherish our annual spring break trips to Hilton Head Island, South Carolina. Have you been? If not, you need to add it to your achievable travel bucket list sooner rather than later. I’m not kidding when I say that everything about this destination makes it easy to relax and be fully present as a family without inflated resort costs, crowds, or lots of travel time.

Hilton head island family trip

So, I’m here today to share all my tips and favorites—from getting there to where to stay, and what to do. That way, you can grab the kiddos, hop in the car, and enjoy this all-American island oasis as much as I do.

hilton head for families

  1. Getting There

If we’re good about packing loads of snacks and commit to a quick drive-thru meal on the way there, it generally takes us about eight hours to get there from Williamsburg, Virginia.

Why would we drive when we could hop on a flight, you ask? Well, we get to bring along our basic comforts of home—our pillows, blankets, books, you name it; there was space to transport everything we needed to be comfortable and happy for the journey.

This year, I let the girls pick out three DVDs each for the ride. Though, I know what you might be thinking. Yes, that’s a lot of screen time. But, this was one of those times when I was going to allow the girls to binge-watch their favorites. And, that’s only because I can rest easy knowing that once we get to the beach, we always end up having way too much fun to even think about burying our heads in an iPad.

Oh, and the fact that my husband won’t be behind the wheel. When it’s his turn to drive, you can typically find me squeezing my eyes shut and trying not to have a full-blown panic attack. That’s because he’s what you might call an offensive versus defensive driver. So, we generally try to share drive time so I can rest my nerves. But, again, as soon as we arrive at our final destination and step foot in the sand, we leave our worries behind and concentrate on unplugging and unwinding!

  1. Where to Stay

We’re fortunate in the fact that we’re able to stay at my in-laws’ place at Harbor Town Yacht Club in the Sea Pines community of Hilton Head Island. Sea Pines is a large community with plenty of vacation rentals, The Inn & Club at Harbour Town, golf, restaurants, a boat harbor, trolley, nature preserve, and every other thing you can think of to keep everyone in the family relaxed and entertained.

The Omni Hilton Head is also a great family-friendly resort pick. That way, you can enjoy affordable and spacious accommodations, and purchase a day pass to soak up all of Sea Pines for $6.

  1. What to Do

There really is so much to do and see here! It’s no wonder it was named the Best Island in the United States by Travel + Leisure. But, I know how overwhelming it can be to try and plan activities that everyone in your travel crew will love. So, here are my top five favorites in no particular order:

  • Rent Bikes

Sea Pines will deliver beach cruisers and pick them up for the week for around $30/per person. We ride bikes every day if we can. There are great paved paths with incredible live oaks, mossy trees, and adventures along the way—including the occasional alligator sighting! Not to mention, the private beach is just a few miles away which you can also venture to by bike. In fact, because of the hard-packed sand, you can actually take your bikes right on the beach!


Sometimes, however, we would opt to drive and park (it’s free) so we could bring along our chairs and cooler, and spend the day playing in the waves. Have I mentioned already that this is one beach where I feel like I can truly relax? Well, it is. The girls can walk way out in the water before it gets too deep and the waves are generally calm.

Salty-Dog-Restaurant Hilton head
Salty Dog Restaurant

No matter how you choose to commute around town—by bike or car, I recommend stopping at the Salty Dog Cafe for lunch. Go early and be prepared to wait. But, it’s so worth it! Once seated, order the fish tacos and mojitos. You won’t be sorry. Our girls loved the shrimp toast and live music!

gregg russell

  • Greg Russell Concerts Under the Live Oak Tree

Greg Russell is a major hit with the kids in Hilton Head. During the spring, summer, and holiday seasons, you can listen to him as he performs a concert on weeknights between 7:30-9 pm under the big oak tree in Harbour Town with a kid-friendly sing-along.

My kids LOVE these shows! It’s the perfect way to end each day in the sun. Best of all, my husband and I can sit and have dinner within eyesight of the girls and watch them happily sing and dance along. Fun fact, we love to eat at The Crazy Crab, Quarterdeck, or Harbourside for super casual, family-friendly dining.

Lawson-Farms hilton head

  • Feed the Animals at Lawson Farms

As a “frugal mama” myself, getting up-charged to death on vacation totally stresses me out. When it comes to this vacation spot, however, there’s so much to do that costs little to nothing. That’s one of the things I love most about it! And, feeding the animals at Lawson Stables is definitely one of them.

Bring apples or carrots with you for the horses or buy goat food for pocket change when you get there. We also love that it’s within biking distance.


  • Dolphin Watch on The Mystique

We never leave Hilton Head without hopping aboard The Mystique for some dolphin spotting. This is a 42’ teak and mahogany yacht that takes guests out in the morning or evening for cruising and dolphin watching. We all love it and make it an annual tradition!

  • Ride the Ferry to Daufuskie Island

This is another absolute must and 100% worth the splurge. We took a quick 10-minute ferry over to the nearly uninhabited island of Daufuskie with only 400 residents and rented a golf cart for the day (approximately $100/daily).

The island is beautiful with gorgeous homes, sandy roads, and fun adventures like the haunted lighthouse. We love the Frosty Frog Cafe for their $1.50 pizza slices and, get this, a selection of frozen drinks served by the gallon to go!

In the end, I can’t say enough great things about Hilton Head Island, South Carolina. The 8-hour drive is well worth it to experience this southern gem of a beach destination with your family. I highly recommend renting a suite that will give you at least a mini kitchen to help with costs and convenience, and a location that makes it easy to get around by bike.

We’re already counting down the days until our next spring break when we get to go back and sing along to Greg Russell under the live oak tree.

We are excited to bring you articles written for us from Frugal Travel Mama at Tripbound, and her local travel-loving mama friends! Unfortunately, Tripbound was forced to close its doors as a result of COVID-19’s effects. We hope their legacy will continue through your travel adventures, they wrote many articles for us here at WilliamsburgFamilies.com to help you plan memorable family getaways!


  • Olivia Bada

    Marketing, communications, sales, writing, and web management all come together when working on published pieces for Localourist, The Burg Weekender, The Burg Weekly and Williamsburg Families.

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