Six Picture-Perfect Proposal Spots in the Lowcountry

You’ve thought about it, you’ve talked about it, and you’re finally ready to take your relationship to the next level with marriage! But first, you have to plan the perfect proposal. After all, this is a moment you and your significant other (and soon-to-be spouse!) will remember for the rest of your lives. The setting needs to not only be just right, but be perfect!

Hilton Head Island is a wonderful place to start your happily ever after. Stunning beaches, South Carolina’s best restaurants, charming streets, elegant historical properties – there’s no shortage of gorgeous settings to ask the most important question of your life. If you have wedding bells on the brain, here are our top six picks for picture-perfect proposal spots in the Lowcountry!


Michael Anthony’s Cucina Italiana

A cocktail on ice

What’s more quintessentially romantic than a candlelit table, a bottle of wine, and a pair of decadent pasta dishes? For an unforgettable dinner, book a table at Michael Anthony’s Cucina Italiana. Modeled after a traditional Italian trattoria, Michael Anthony’s serves handmade pastas, succulent meat and seafood dishes, and delicious desserts, all using the freshest ingredients. With its cozy interior, extensive wine list, and a menu that’s perfect for sharing, it’s no wonder Michael Anthony’s has been chosen as Hilton Head Island’s most romantic restaurant by TripAdvisor contributors.

Prefer to pop the question in a more private setting? Sign up for one of the eatery’s cooking classes, then whip up your own gourmet meal at home – we can’t imagine a more perfect night in!


Old Town Bluffton

Old Town Bluffton

Stroll the streets of charming Bluffton, SC where towering mossy oaks, stately columned homes, and friendly faces transport you back to a simpler time – and love is always in the air! A Bluffton walking tour is the perfect day date, and there are plenty of perfectly Instagrammable proposal spots along the way. Linger on Calhoun Street, the heart of Old Town Bluffton, which is lined with one-of-a-kind shops and restaurants, gorgeous historic properties, and colorful galleries and markets. Start your day at The Corner Perk Café for brunch or an iced coffee or a sweet tea to go, then discover all the delights that beautiful, historic Bluffton has to offer while making a special memory you’ll never forget.


Bike Tour of Hilton Head Island

A bike on a stretch on white beach

Pack a picnic lunch and rent bicycles – or, to make it really romantic, spring for a bicycle built for two! With more than 60 miles of trails, including 12 miles of bike-friendly, hard-packed beach, exploring Hilton Head Island by bicycle is easy and, you guessed it, romantic. Find a secluded spot on the dunes, a shady lane, or a picturesque park – there are countless places to woo your loved one in the Lowcountry. Looking for a quiet spot? Check out these hidden bike routes – little-traversed paths that should give you and your sweetie a bit of privacy!  No matter what time of day you head out – a sunrise bike ride, a sunset pedal to close out the day, or anything in between – magical moments await when you’re biking on Hilton Head Island.


Daufuskie Island

Sunset over the ocean

From the instant you step onto the boat that will whisk you away to Daufuskie Island, you’ll feel enveloped in the charm of this Lowcountry gem. With few paved roads and no bridge to the mainland, Daufuskie’s charm makes every visitor feel like they’ve stepped back in time, to a simpler, sweeter era. No wonder it’s the perfect setting for a marriage proposal! Miles of pristine, peaceful beaches, unique shops and eateries, enormous mossy oak trees…you won’t have to look very far to find a beautiful spot to create an unforgettable memory with someone special.


Beaches of Hilton Head Island

Pink sunset over a beach

It doesn’t get much more romantic than a long walk on the beach, and on Hilton Head Island, there’s no shortage of sandy dunes that were made for leisurely hand-in-hand strolls…and popping big questions! More than 12 miles of sand and surf await. Head to Burkes, Islanders, or Dreissen Beach early in the morning to catch a postcard-worthy sunrise and start the day on an incredible note. Coligny Beach is another fantastic option for a walk, easily accessible with nearby parking and dining for a celebratory post-proposal dinner.


Harbour Town

Sunset over a lighthouse

In the evening, head to picturesque Harbour Town to watch the sun set. Climb the 114 steps of the Harbour Town Lighthouse for spectacular sunset views, or grab a spot on the dock to listen to live music, watch dolphins play, and see the sun go down over the water. If you’d like to share your special evening with friends, book a sunset dinner cruise with a group of 10 or more aboard the Spirit of Harbour Town with Vagabond Cruises. Enlist a friend to capture a photo of your proposal, which you can use on your save-the-date cards or in your wedding décor! Just make sure to invite pals who can keep a secret – you don’t want to ruin the surprise.

Ready to start planning your romantic escape to Hilton Head Island? We’d be thrilled to help you make your special day a perfect one! Sign up now to become a Hilton Head Insider, request your copy of the Hilton Head Island Vacation Planner and be sure to check out our best travel offers as you plan your unforgettable proposal adventure.

An Old Fashion on ice

Find Your Island Time

Hilton Head is America’s favorite island, offering 12 miles of pristine beaches and everything you need for the ultimate retreat. Enjoy easy days relaxing in the sun, sand and surf on some of the best beaches in the country.
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