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14 *More* Ways to Celebrate Valentine’s Day On and Around Hilton Head Island

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Our previously posted guide has helped visitors and locals figure out what to do on Valentine’s Day (and date nights in general) for the past two years, and we decided it was time for a little update. Instead of completely reinventing the wheel, we’ve decided to add to the initial list, 14 Things to Do on Hilton Head Island for Valentine’s Day, which you can read below.

Daytime Activities

The Classic Coffee Date

Hilton Head Island has a ton of great spots to grab a cup of joe and enjoy the views. Start your Valentine’s Day off right by sharing a latte with your loved one and either sit back, relax, and begin to plan your day’s adventures, or take that java to go—you’ve got a busy day ahead!

Need a coffee shop recommendation? Click here for a list of some of the best coffee shops on Hilton Head Island!

Take a Spin on a Street Legal Golf Cart

Have you heard? The best way to explore the Coligny, Pope Avenue, and Palmetto Bay Marina areas is by golf cart! There are 4- and 6-seater golf carts available to rent from Wheelz of Hilton Head—but don’t wait to make your reservation! Ensure you get a cart by calling the friendly folks at Wheelz since golf cart rentals are 50% off throughout February! Click here to learn more.

Make a Stop at the Art Cafe

While you’re in Coligny Plaza, why don’t you try something new with your significant other? Pick out a piece to paint for each other and you’ll both have a memento to remember not only your trip to the island but of this special dayReservations are required, and painting and dining with the restaurant below the Art Cafe, Rockfish Seafood and Steaks, begins at 4pm. Click here to learn more.

See the Sights by Segway

Exploring the island by segway is a unique experience that would be a great way to surprise your significant other. One look at Hilton Head Segway’s schedule of tours might make your head spin, and you’ll definitely have a decision on your hands. Starting from an early Sunrise Tour at 7:30am until their last scheduled Ultimate Discovery Tour at 3:30pm, there’s sure to be a tour to catch your eye. See the schedule here to book.

Visit a Brewery

Believe it or not, there are quite a few breweries on Hilton Head Island. Scattered throughout the island, you’ll find tap rooms that offer tastings, bites to eat, a great atmosphere, and even live music. If you’re interested in how everything’s made, look into scheduled tours! Read our guide on Hilton Head Breweries here.

Not into beer? We have a guide about local wineries and distilleries as well!

Set Sail for a Lowcountry Lunch

In our first article, we mentioned the Valentine’s Day Dinner Cruise by Vagabond Cruise–which is happening again this year, so get your tickets while you can! If you’re looking for something similar during the day, Vagabond Cruise offers a Lowcountry Lunch Cruise. You can decide whether you’d like to be seated inside or outside, but this experience is a buffet and great for all ages.

The best part? It’s not just a cruise exclusively happening on Valentine’s Day, so you can save this activity for later! Learn more here.

Explore Daufuskie Island

Speaking of cruising, you’ll have to take a ferry or jump on a more private cruise to make the trip over to Hilton Head’s neighbor, Daufuskie Island. This secluded island prioritizes natural beauty over paved roads, and it’s safe to say you’ll never have experienced anything like it. Rent a golf cart to make exploring this island easier, or even trade your wheels for a saddle and see the island on an hour-long trail ride led by Daufuskie Trail Rides at Haig Point.

Take a Trolley Through Savannah

This list has certainly taken a detour away from activities on Hilton Head Island, but venturing over to Daufuskie Island or even Savannah isn’t a chore at all! Both locations have a ferry that runs from Harbour Town by Vagabond Cruise. But if you have a car, it’s an easy hour’s drive to Downtown Savannah from the island. Once you’re there you can buy 1-Day tickets from Old Town Trolley that lets you hop on and off at all 15 stops throughout the city. February is one of the best times to visit Savannah, so even if you don’t make it there on the 14th, you should add it to your trip’s itinerary.

Grab a Sweet Treat

Specifically, a frozen sweet treat! Coligny Plaza alone has two great places to grab a cone, cup, or milkshake: Rita’s Italian Ice and Frozen Custard and the Frozen Moo. If you have a craving for some frozen yogurt, head to Sweet Frog Frozen Yogurt so you can create a masterpiece of all of your favorite toppings to share.

Evening Activities

See August Wilson’s “Fences” at the Arts Center of Coastal Carolina

Going to a theater production is also a great way to celebrate a special occasion, and on this February 14th, the Arts Center of Coastal Carolina is featuring August Wilson’s, “Fences”. Wednesday’s show is scheduled for 7:30pm and tickets can be bought online–but don’t wait, make sure to buy your tickets before it’s sold out! Learn more about this play here.

Get Tickets to See Comedy Magic Cabaret

Set for 8:00pm on February 14th, spend an evening filled with comedy and magic with James Brandon and Gary Maurer. Definitely a unique experience, you’ll be rolling with laughter from the performers’ “Funny Not Filthy” sets. While you enjoy the live entertainment, you can also snack on some delicious d’oeuvres that range from savory to sweet, and sip on some wine, beer, and specialty cocktails. Purchase your tickets here.

Dance the Night Away

Every Wednesday night–unless there’s a special event taking place–the Rooftop Bar at Poseidon hosts a Coastal Country Night. Directly following the Sunset Celebration from 4-7pm, complimentary line dance lessons are given for about a half hour. Line dancing lasts until 9pm, but stick around for a DJ Dance Party starting at 10pm that plays all the Top 40s.

Go to a Trivia Night

If you’ve got two left feet but still want to go somewhere so you can be a part of the action, head to one of the trivia nights on Hilton Head Island! You’ll have a choice between attending Mellow Mushroom’s or Earle of Sandwich’s trivia nights since they’re both scheduled for every Wednesday night. Both located on the south end of the island, Earle of Sandwich starts their game at 7pm, and Mellow Mushroom starts theirs at 8pm.

Have Dinner at Kind of Blue

Not only will you be able to order from a musically-inspired (and hilariously-named) menu offering plates like the Marley Flatbread, Johnny Cash Ring of Fire Salmon, or even the Nick Jonas Likes Tuna, but you’ll be able to have a great seat to enjoy that evening’s entertainment. Open from 5-11pm, the live entertainment is scheduled to start at 7pm on Wednesdays. Keep an eye on the schedule for who’s set to perform on the 14th!


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