Hilton Head Island, South Carolina – My New Favorite Place in America

Hilton Head Island, South Carolina is my new favorite place in America! I took my kids to Hilton Head during the first week of December to enjoy a week at Smith Stearns Tennis Academy. It was one of the best get-aways I have ever experienced.

Of course, December is not the ideal time to experience Hilton Head or any beach trip destination. But I found plenty to do while the kids were playing tennis.

We stayed in a Third Home property in Sea Pines Resort on the southern tip of Hilton Head Island. Sea Pines Resort is a 5000 acre oceanfront gated community offering countless activities and amenities: golf, tennis, kayaking, shopping, spa, tours…to name a few. Sea Pines also has over 12 miles of trails for walking or biking.


Our property was walking distance to Harbour Town – the picturesque village of Hilton Head Island. Harbor Town spawns dozens of yachts, boutiques, restaurants and activities.

The center of Harbour Town is the light house and museum. For $4 per person, you can climb to the top of the light house and take photos at the top. Along the climb to the top of the lighthouse are penny-flattening machines. My kids loved this.

hilton head harbour town lighthouse

Steps away from the lighthouse is a little t-shirt shop called Camp Hilton Head. I bought a t-shirt for myself, a coffee mug and “HH” bumper sticker for my car here.


Bike riding distance from our exchange property was the Sea Pines Beach Club. This is where the ocean-front activity is. Sea Pines Beach Club has a waterfront restaurant, bar, Surf Shop, Surfside Market for more casual meals.

hilton head sea pines beach club


The best restaurant in the Sea Pines Resort area (we went back three times!) was The Bakery at Harbour Town. The Bakery’s name is misleading. They actually serve the best chicken quesadilla I have ever had (I am a Texas girl and we are raised on quesadillas) made with fresh vegetables.

Their hamburger with a side Mediterranean Salad was divine. And my son cried (not kidding) when he took his last bite of his pancakes one morning.

Our favorite restaurant outside of Sea Pines Resort (but only 10 minutes away) was a family-owned Italian restaurant Pomodori. My daughter found this restaurant online.

Pomodori is nestled behind a strip mall at the end of the parking lot. You won’t see it driving by. Make reservations or get there early because Pomodori was packed on a Tuesday night in the dead of winter.

hilton head best restaurant pomodori italian

Another wonderful restaurant was nestled in the heart of Harbour Town – The Crazy Crab. Surrounded by yachts on the edge of the marina, The Crazy Crab is sure to be a hit during the warmer months.

I loved the shrimp and grits – and my kids loved their kids’ menu (which is sometimes a feat at seafood restaurants). If you experience a long wait, there is a huge playground steps from the restaurant the kids can enjoy while you wait.


hilton head harbour town restaurant crazy crab



I am jealous of those who live in Hilton Head year round because there are so many fun activities to keep you busy. There are two prestigious tennis acadamies minutes from each other: Smith Stearns Tennis academy and Van Der Meer Tennis Academy – both offer junior and adult programs.

Smith Stearns is located inside Sea Pines Resort and is a 1 minute walk to Harbour Town and the lighthouse. There are also racquet clubs and neighborhood courts on almost every corner in Hilton Head.

smith stearns tennis academy hilton head

Also inside Sea Pines Resort are three award-winning golf courses. The Atlantic Dunes was awarded National Course of the Year. I am not a golfer, but it is clear that golf is king in Hilton Head and the golf courses are pristine.

hilton head golf sea pines resort


One day while we were in Hilton Head it was pouring rain, so that gave us an excuse to go shopping. 🙂 First, just of over the Hilton Head bridge back on the mainland are the Tanger Outlets. This is where you will find the bulk of big store shopping (Nike, H&M, JCrew, Under Armour, Michael Kors, etc…)

Slightly more upscale than the Tanger Outlets is Shelter Cove. The perk of Shelter Cove is the playground. Use your negotiating skills well here: “If you let mommy shop for an hour, you can go to the playground! Deal?” Shelter Cover is scattered with boutiques, but there is also a TJ Maxx and Whole Foods nearby (my faves!).

hilton head shelter cove shopping playground


hilton head shelter cove shopping playground

I know a place is magical when I can enjoy the outdoors in 40 degree temperatures. Hilton Head Island was chilly the week we were there in December, but it was awesome. I encourage you to make a trip to Hilton Head – especially if you are a tennis or golf fan. it won’t disappoint.

hilton head island south carolina






Have you been to Hilton Head? What other tips can you share?

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