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26 Jan 2022
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What to Do

Are you planning the picture-perfect Valentine's Day trip to Hilton Head Island? Planning a romantic vacation is never easy, but our slice of paradise on the South Carolina Coast boasts 12 miles of pristine beaches and great waterfront views, so there are plenty of things to do for couples on your Hilton Head Island getaway.  

Request our free 7-Day Itinerary when you're ready to start planning your romantic getaway. This planning tool contains local insight on how to spend each day of your Hilton Head Island vacation! 

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5 of the Best Things to do on Valentine's Day on Hilton Head Island

Wine Tasting 

Wine and romance have been together for thousands of years, and Hilton Head is home to several award-winning wineries. Island Winery opened in 2006 and has become well known for their Lowcountry Fruit Wines. 

Island Winery features daily testings from 12 pm to 5:30 pm with a wide selection of red, white, and Lowcountry specialty wines. With a mix of indoor and outdoor seating, an afternoon wine tasting trip is a great mid-day pick me up this Valentine's Day. 

Dinner/Sunset Cruise

 Sailing the near shores of Hilton Head is both relaxing and breathtaking during dusk. Plan a rowdy happy hour cruise with The Salty Dog or take a more traditional, romantic approach with Vagabond Cruise. Whoever you choose, a dinner or sunset cruise is a great way to have a good meal and a good time with a romantic backdrop. 

If you are looking to stay onshore but enjoy a beautiful waterfront dining experience, we love Hudson's Seafood House on the Docks, Ela's Blu Water Grill, and Skull Creek Boathouse. 

Horseback Riding on Daufuskie Island 

Dafuskie Island is the definition of a hidden gem. The South Carolina island is only accessible via ferry and boasts 400 residents. The Island is home to historical trails, museums, and several dining options, but it is not entirely walkable, so we recommend renting a golf cart to traverse it. 

A great romantic option is a beach horseback riding adventure with Daufuskie Trail Rides. The only beach that allows horseback riding in the Lowcountry, Daufuskie makes for the perfect romantic romp across the beach, watching the waves crash gently on the shore. 

Listen to Live Music at Night

Hilton Head takes pride in its food and nightlife scene. If you are looking for a rooftop bar for a good drink and view of the sunset then you should visit the Rooftop at Poseidon. If jazz music is more your speed, check out The Jazz Corner from 6 - 11 pm for a charming evening filled with the dulcet tones of the Hilton Head Island jazz scene. 

Hiking and Walking Trails

"I like long walks on the beach" is one of the most iconic dating bios, but for a great reason! If you are looking to take one of those long walks on a more secluded beach with your significant other, we love Fish Haul Beach Park or Burkes Beach. 

We are a big fan of natural beauty, and the Sea Pines Forest Preserve is one of those gems you have to see in person. Combining Native American history, acres of protected flora and fauna, and a secluded place to picnic, you can plan a great Valentine's Day at Sea Pines Forest Preserve. 

Bonus: Relax at Your Vacation Rental 

The most important part of your Valentine's Day vacation is where you are staying! Beach Properties has villas and 1-bedroom condos all along the island to match whatever your desires are! From the scenes of the lagoon to the gentle sound of waves crashing along the shoreline, you cannot go wrong with a Beach Properties vacation rental. 

Check out our romantic one-bedroom offerings below! 

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