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 day. Reservations are required. 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 tour at 9:00am until their last scheduled Eco Fun Ride or Eco Discovery Tour at 5:00pm, 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 Donuts and Dolphins
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 another cruise earlier on in the day, Vagabond Cruise offers a Donuts & Dolphins Cruise.
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 “The Play That Goes Wrong” 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 “The Play That Goes Wrong”. Saturday’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 Tim Hill and Host, 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
The best nightlife on the island can be found at the Rooftop Bar at Poseidon. Located mid-island in Shelter Cove Towne Centre above the restaurant, Poseidon, the Rooftop Bar is known for having an energetic lineup of live music and DJs throughout the year. While there’s no specific event scheduled for Saturday, February 14th, start off the celebration on Friday night with a one-night-only reunion performance by Free Shotz. This 21+ event starts at 9pm and there’s a $5 cover charge or $200 VIP Booths available for 10 people. Buy your tickets ahead of time online!
Catch a Show in Big Bamboo’s 4th Annual Winter Concert Series
Apart of Big Bamboo’s & Tito’s Vodka 4th Annual Winter Concert Series, Saturday night’s show features the band, Peach Patrol, a group that plays a variety of covers as well as their original music. Benefiting the Hilton Head Humane Society, the show will start at 8:30pm and attendees will be able to not only rock out to some great music, but order off of Big Bamboo Cafe’s delicious food and drink menus.
Have Dinner at Kind of Blue
Not only will you be able to order from a musically-inspired, star-studded menu offering plates like the Bob Marley, Nick Jonas, Aretha Franklin and more, but you’ll be able to have a great seat to enjoy that evening’s entertainment. This Valentine’s Day, there will be two special events: the STEE and Malcom Valentine special 3-course meal, and the Donte Jones special 3-course meal. Learn more on Kind of Blue’s website!
