If you grew up in Ohio, chances are you’ve spent at least one family vacation on Hilton Head Island. [Even HHI locals know it and cater witty banter and jokes to the stereotype.] But, just because you may have spent one or two [or more?] summer vacations here, doesn’t mean there’s not still more to be discovered. Prior to this most recent trip, I had visited HHI three times and still, this time I experienced the island in a completely new way. Here are a few must-sees and must-dos for your next trip!

Pro-tip: Upon arriving on the island, be sure to rent a bike from one of the many bike rental companies in the area. The beauty of a small island is the fact that pretty much anywhere you go can be reached by biking [as long as you’re willing to put in the mileage ;)].


Photo courtesy Jacinta Harshe

Kayaking with Saltmarsh Paddle Tours

Looking to add a little bit of an adventure to your typical beach vacation? Saltmarsh Paddle Tours, established more than 60 years ago, offers guided and non-guided kayaking tours Wednesday through Monday from 8:00 a.m. to 7:00 p.m. and Tuesday from 8:30 a.m. to 8:30 p.m. Guides encourage you to view Hilton Head’s diverse marine life up close [bonus points if you can spot a dolphin!]. The two-hour excursion allows for plenty of time to paddle leisurely, taking time to embrace the wildlife that inhabits the coast. 

Harbour Town Day Sail

In 1987, Dennis Conner sailed the Stars & Stripes vessel in the 26th America’s Cup [a sailing contest], the oldest international sports competition. After winning four races and reclaiming the Cup for the USA, America’s Cup ’87 is often considered to be one of the greatest of all time. Now, Stars & Stripes is open to the public. Sailing out of Harbour Town Monday through Saturday at 2:30 p.m. and 4:30 p.m., the sailboat can accommodate up to 25 passengers with a captain and two deckhands at your service. Soak in the sun while you sail around the island on this 90-minute tour and experience Stars & Stripes in all of its glory.


Sweet Carolina Cupcakes

Just like its name states, Sweet Carolina Cupcakes [located in Coligny Plaza] are on a whole other level of sweetness. These gourmet, freshly made cupcakes are offered in two sizes: mini and large. There’s no in between. While the mini cupcakes are just the right size to temporarily satisfy your sweet tooth, you can’t help but be left wanting more. But, with the rich icing and dense cake, the large cupcakes are a bit too much for one person to handle. My family’s solution? Buy a bunch of large cupcakes and cut them into fourths … this also offers the perfect excuse to taste-test multiple flavors [my favorite was definitely the strawberry cupcake topped with strawberry icing].

Frozen Moo Ice Cream

Still craving more after those cupcakes? Frozen Moo Ice Cream is just around the corner in the same plaza and is the perfect relief after a long, hot and humid day at the beach. The rich, creamy ice cream is offered in a variety of flavors [listed two columns long in tiny font on a menu, to be more precise]. Fortunately, the long line that often spills out the door provides ample time to choose which flavor to go with [we promise, the ice cream is worth the wait]. Warning: one scoop of Frozen Moo is comparable to two scoops elsewhere, so decide accordingly 😉


The Jazz Corner

As a passive fan of jazz music [meaning I only really listen to it with people who are avid fans], I wasn’t sure what to expect when my family said we were going to a dinner at The Jazz Corner. However, after being seated [and learning that it was acclaimed as one of the top “100 Great Jazz Rooms” in the world by Downbeat Magazine] I was immediately intrigued. The small dining room includes a handful of tables to seat four while smaller two-tops line the wall. Louise Spencer & Lavon Stevens have been performing at The Jazz Corner for 15 of the 20 years that it’s been open [and with Spencer’s silky smooth, soulful voice and her playful stage banter with Stevens, it’s easy to see why]. The mouth-watering entrees add the perfect complement to the night’s entertainment. 

Side stop: Savannah, Georgia

Though it’s common to tackle the 10[ish]-hour drive from Ohio to Hilton Head, my family decided to fly instead this year. Like most HHI tourists, we flew into the Savannah/Hilton Head International Airport … meaning that with our departure time of 9:30 p.m. on the last day, we had a LOT of time to kill. The historical building blocks of Savannah, Georgia run too deep to squeeze into one day, so we decided to explore the shopping instead [if you know me, you’re probably not shocked reading that]. I hadn’t heard much about Savannah before, but was pleasantly surprised by the culture and art that flourished within the small part of the city I visited.

City Market

After walking from the visitor’s center [with no real destination in mind], we stumbled upon Savannah’s City Market. The architecture and atmosphere of the restaurants, cafes and boutiques that lined the street mimicked a blend of New Orleans’ French Quarter and Seattle’s Public Market [or at least the pictures I have seen of them … those two still go unchecked on my bucket list]. I couldn’t help but stop at Byrd’s Famous Cookies the minute I saw the slogan “May your cookie jar never be empty.” [We’ve already established I have a massive sweet tooth, right?] The crunchy, bite-sized cookies were some of the best I’ve ever tasted [granted, I usually eat break-and-bake from Pillsbury, but still]. I even left with a jar to bring home!

Broughton Street

After browsing the market, we ended up on Broughton Street. If you’re looking for typical name brands [Banana Republic, Urban Outfitters, etc.] this is the place to be. However, scattered throughout the big corporations are many locally owned cafes and boutiques. I stopped in a few that showcased work made by local artists, my favorite of which was Arrowleaf Boutique [thanks for my new sunglasses!]. It’s both a blessing and a curse that I was out of space in my luggage … I truly believe I would have bought everything in that store!

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One thought on “Discover: Hilton Head Island, South Carolina

  1. Thought I would never want to go back to Hilton Head or Savannah but after reading your blog, now I do. Just to visit the places you mentioned in your blog. 👍


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