Kiawah Island: 20+ Years of Tips, Favorites & Hidden Gems

I’ve been traveling to Kiawah Island for over 20 years, and it’s one of those places that just never loses its magic for my husband. While I’d rather be flying overseas with a jam packed itinerary exploring the world, I have grown to love Kiawah. Whether you’re going for the beach, the golf, or simply to slow life down, Kiawah delivers. Over the years, I’ve tried different rental companies, found my favorite restaurants, and learned the “insider” tricks you only get from repeat visits. Here’s my take.

⸻

Where to Stay

We’ve rented through Akers Ellis and Sweetgrass Properties and have liked them both. Typically, these companies offer a $200 credit toward bike rentals or beach gear, which is incredibly useful given the beach distance from most of the houses.

Pool Access Tip:

If having pool access is important, you must rent through Kiawah Island Resort (the official resort) or rent a private home with its own pool. Only property owners or Kiawah Island Resort guests can access resort pools.

You can also stay at The Sanctuary, Kiawah’s luxury oceanfront hotel, and it’s phenomenal. The spa is wonderful—go early or plan to stay after your treatment to enjoy the plunge pool and sauna.

⸻

Getting Around

Unless you’re staying at The Sanctuary or in an oceanfront rental, rent bikes. There’s no public parking for beach access, and some walks can be very long. With bikes, you can get almost anywhere on the island easily. If your rental company doesn’t provide recommendations or a credit, I recommend using VayKLife. They have plenty of other outdoor toys you can rent too!

⸻

The Feel of the Island

One of the best parts of Kiawah is that it’s a gated island, giving it a safe, private feel. If you stay in Vanderhorst, it’s gated within the gated island—double the security and peace of mind. Even with some ongoing construction, I’ve always felt safe enough to let my kids bike all over the island.

That said, unless you golf, play tennis, or pickleball, there isn’t a huge list of activities—Kiawah is all about a slower pace.

⸻

Groceries & Local Favorites

There’s a Harris Teeter at Freshfields Village (right before the island), or you can stop at a grocery store on John’s Island before arriving. The off-island grocery is cheaper, but the quality and options are limited.

Don’t miss:

• Rosebank Farms – Fresh seafood, local veggies, and our family’s must-have: homemade key lime pie and crab dip!

⸻

Where to Eat

On-Island & Freshfields Village:

• The restaurants inside The Sanctuary are always a great option (fine dining & casual available)

• La Tela Pizza, King Street Grille, Fuji Sushi, Cantina 76 Mexican restaurant, FortyEight Wine Bar (for a nice glass in the evening) and Ben & Jerry’s at Freshfields

• Salty Dog Café on nearby Seabrook Island

• Mingo Point Oyster Roast (Mondays) – All-you-can-eat oysters & Southern buffet, live music, great for kids to run around. Expensive, and in my opinion, not the best food for the price unless you really love oysters.

• Cherrywood BBQ & Ale House at Osprey Point Golf Club – a must-visit for BBQ lovers, with tender smoked meats, a great bourbon selection, and scenic golf course views.

•The Ocean Course Clubhouse – perfect for lunch or dinner with panoramic ocean views, fresh coastal dishes, and a front-row seat to one of the most famous golf courses in the country.

Off-Island (John’s Island):

• Wild Olive – Our family’s absolute favorite (reserve 4 weeks in advance during summer)

Lobster Risotto

• The Royal Tern – Excellent seafood and cocktails

Seafood Tower

Charleston Favorites:

• The Ordinary – Upscale seafood

• Leon’s Oyster Shop – Famous fried chicken & oysters

• Oak Steakhouse – Sister restaurant to Highlands, NC

• Peninsula Grill – Legendary coconut cake

⸻

Day Trips & Shopping

Charleston:

Walk King Street from end to end—it’s always worth it, no matter which stores are there at the time. Park in the garage at the Charleston Place Hotel on Market Street for easy access to both King Street and the City Market.

For men’s business attire, 319 Men is a family-owned gem—my in-laws have shopped here for over 40 years.

Mount Pleasant:

For more mainstream shopping and big-box retail.

⸻

Outdoor Fun & Activities

• Kayak from Mingo Point or the marina before the island split. Watch the tides—trying to paddle against them is exhausting, especially with little kids (ask me how I know 😅).

• Moncks Corner – Worth the drive to see Cypress Gardens

   • Angel Oak Tree – A short drive to John’s Island, this massive live oak is estimated to be over 400 years old and is a must-see for its size and beauty.

• Charleston Tea Garden – The only tea plantation in North America, offering trolley tours through the tea fields and a fascinating look at how tea is grown and made.

• Seashell Hunting – Head to the far end of Kiawah where the sound divides the island from Seabrook. It’s one of the best shelling spots, especially at low tide, and you’ll often spot sand dollars and conch shells.

• Horseback Riding on Seabrook Island – The Seabrook Island Equestrian Center offers scenic rides along wooded trails or right on the beach.

• Fishing – Kiawah has several brackish ponds and soundside areas where you can cast a line; expect redfish, trout, and flounder. Many spots are catch-and-release, so check regulations.

For Kids:

• Camp Kiawah – Drop-off program with activities

• The Turtles’ Nest Art Studio – Paint pottery and crafts

• Night Heron Park Pool – Home to the most epic water slide on the island

Final Thoughts

Kiawah isn’t about hustle—it’s about slowing down! Between the gated privacy, pristine beaches, and bike-friendly paths, it’s a place where kids roam free and adults can truly relax.

Just remember: plan your meals, rent your bikes, and don’t underestimate the power of a Key Lime Pie from Rosebank Farms to make your trip complete.