How to do Hilton Head Island, SC, in 48 Hours

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The beach is like humanity’s charging port. The longer we stay, the more we feel “recharged” and ready to face our daily duties further inland. 

Trouble is, we often can’t stay “plugged in” for long. Beach vacations aren’t cheap, and with PTO being consumed by weddings and family holidays, there may not be much time left for curling your toes in the sand. 

So what if you only have 48 hours to “do” a famous beach destination like Hilton Head Island? What’s the ideal itinerary to take your “trickle charge” to a “fast charge” on the pristine white beaches of South Carolina? To find out, my partner, Holly, and I took a 48-hour jaunt to the Atlantic Coast – and to our “shock,” our brief adventure ended up feeling twice as long in the best way possible. 

So without further ado, here’s how to do Hilton Head Island in 48 hours.

Day 1

Day 1 checks off the essentials: sunshine, beach and a little bit of exercise to make room for dinner. We begin our 48-hour adventure with America’s new favorite pastime and the bane of countless HOAs. 

Morning: Pickleball at Palmetto Dunes Pickleball Center

Without realizing it, I’d worn an effective form of camouflage to confuse my adorable opponent.

Photo by author

I’m a huge fan of starting off any vacation with a little exercise. Not only does it boost your energy and mood – it also makes room for all the well-deserved carbs and butter you’ll inevitably consume over the next few days. 

Hilton Head has no shortage of light exercise options (heck, Beach Cruiser Bikes are practically the standard mode of transit), but there’s something extra special about playing pickleball by the beach. Palmetto Dunes Pickleball Center is just a five-minute walk from the ocean, meaning the occasional seabreeze makes its way through the trees to cool your brow as you dive for that short shot in the “kitchen.” 

Lessons are also highly affordable and well-taught by seasoned instructors. You can register here. 

Afternoon: Beach (Of Course)

Hilton Head’s beachfront is the opposite of Miami’s or Panama City’s; it’s quiet, sparsely populated, and perhaps best of all, uncommercialized. Generally speaking, you won’t hear boomboxes or see biplanes pulling banner ads that read “$5 MARGS AT FAT TUESDAY’S.” 

Nope. Just the waves crashing, kids giggling and the occasional seagull cawing at the sight of unguarded pizza. 

It’s a postcard in audible form. 

Hilton Head’s beaches are also shockingly flat and wide, leaving plenty of room for jogging, biking or bocce ball without disturbing your neighbors. 

So take your time absorbing the sun’s rays, and when you start to feel peckish, check out the menu at Blue. 

Evening: Dinner at Blue

As you can imagine, Hilton Head has numerous fine dining establishments that offer top-quality steak, seafood or both. And while I can’t say I’ve tried even 20% of them, I can say that we had a lovely time at Blue, the in-house option at Hilton Head Beachfront Resort and Spa. 

Featuring high-tops and waterfront views, Blue calls itself “casually upscale” – which sounds like an oxymoron, but actually makes sense once you see it in-person. It’s handsome and simple, like the inside of a Tesla. 

Food-wise, Blue’s menu features a curious mix of American and pan-Asian cuisine. From locally caught fish to Asian potstickers, Shrimp “Cargot” to Miso-glazed sea bass, we had no shortage of options. 

But we tried not to overeat and impact our sleep quality, because in 12 hours, we start Day 2 with a detox. 

Day 2

We’re now just 24 hours into your highly efficient Hilton Head adventure. So far you’ve hit the beach, left skid marks on the pickleball court and sampled some fine dining. 

On day 2 we’re going to explore the island a bit more – but first, let’s relax your shoulders. 

Morning: Spa Retreat at Spa Soleil

The “spa” portion of the Hilton Beachfront Resort & Spa is called Spa Soleil, and despite being attached to a resort, the prices for massages, facials etc. are highly reasonable. 

I was pleasantly surprised by the atmosphere, too – instead of a tiny, humble waiting room with an expired issue of Men’s Health on a coffee table, Spa Soleil features an expansive relaxation room with day beds, a fancy tea selection and a peaceful, wall-sized waterfall fountain. The locker rooms boast large showers, toasty saunas and complimentary razors/toiletries etc. to help you fully freshen up. 

Oh, and my facial was excellent. 

All told, Spa Soleil gave me the authentic, holistic spa experience I was looking for – and I can’t imagine a better way to start Day 2.

Now it’s time for pirates. 

Afternoon: Mini Golf at Pirate’s Island Adventure Golf

I’ll admit that I felt a weird sense of trepidation taking Holly to play mini golf. Would fond childhood memories translate to a fun, nostalgic romp 25 years later? Or would we simply get feasted on by mosquitoes as we cursed another frustrating double-bogey? 

To my own surprise, neither was the outcome. As it turns out, minigolf is so freaking fun as an adult that you don’t need nostalgia to fuel the experience. 

Pirates Island Adventure Golf is also the closest thing you’ll find to a “5-star” minigolf experience, with high-budget props and design, varied challenges and authentic sea shanties emanating from hidden speakers. You’ll even find historical markers at each hole describing the trials and tribulations of real-life pirates like Edward Teach aka “Blackbeard” –and the hapless lawmen pursuing them. 

For less than the cost of a movie ticket, an 18-hole adventure at Pirate’s Island is a 90-minute jaunt you won’t regret. Plus, it’s heavily shaded – meaning you may not have to change outfits before your sunset dinner in Harbour Town. 

Evening: Harbour Town and Crazy Crab

As a capstone to your 48-hour adventure in Hilton Head, why not explore Harbour Town – land of small shops and big yachts? 

Situated next to Sea Pines Resort and golf course, Harbour Town is a playground for Hilton Head’s wealthier denizens (hence the stiff competition for yacht parking). It’s also part of a vast private neighborhood on the “toe” of the island, which is why you’ll have to pay $9 for a visitor’s pass at the entrance gate well before you reach the pier. 

So is it really worth it? 

Yes. Because not only is Harbour Town home to some of the best ice cream and romantic vistas on the island – it’s also home to The Crazy Crab Harbour Town, my personal favorite eatery on the island. 

Despite its lavish surroundings, The Crazy Crab is decidedly unpretentious – like Pirate’s Island, it’s packed with old-timey maritime props like diving suits, driftwood and busts of Captain Morgan to set a vacation-y mood. 

But the quality of the food speaks for itself. It wasn’t long before Holly and I were consuming fresh, hot hushpuppies faster than a woodchipper, leaving little room for my actual dinner. So I ordered the “half portion” of the seafood broil, not realizing it meant half a ton. 

Needless to say, you will not leave The Crazy Crab hungry. 

That concludes our 48-hour adventure through Hilton Head. From ample beach time to pirate minigolf, an overdue spa retreat to a walking date through Harbour Town, we’ve successfully covered the island’s greatest hits without feeling too rushed.

Hopefully, this efficient itinerary will help you turn your “trickle charge” into a “fast charge.” 

And for more tips on maximizing your next travel adventure, stick with The Travel 100. 

– Chris Butsch