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Hilton Head Itinerary – Best Things to Do on the Island in 2 Days

Today I want to bring you my Hilton Head itinerary for South Carolina. This island off the coast in the American South is known for golf, but there’s a lot more to it than that. From beaches to biking and Lowcountry dining, there are loads of fun things to do in Hilton Head. I’m here for 2 days, and I can’t wait to show you the highlights of this part of the United States.

Hilton Head Itinerary

Hilton Head Itinerary

My Hilton Head itinerary is a segment of a larger trip I’ve planned to Georgia and South Carolina. My time here was preceded by 2 days in Savannah, and it will be followed by 3 days in Charleston.

Given I’ve had an amazing time so far, I arrive on the island with high expectations.

I’m not a golfer, so my plan is to discover the best things to do here away from the fairways. I’m excited to see what the island has in store.

Hilton Head Beach

Day 1

My boyfriend and I leave Savannah in the morning and make the 45-minute drive to Hilton Head to start our trip.

Hilton Head Beach Umbrellas

Hilton Head Farmers’ Market

We arrive in time to pick up a quick breakfast at the weekly Hilton Head Farmers’ Market, which takes place every Tuesday at the Coastal Discovery Museum’s Honey Horn campus.

Hilton Head Farmers Market

The market stalls are arranged in a big circle in a field, and there’s live music to welcome us.

As we make our way around the market, we find everything from eco-friendly household products (we buy re-usable sponges) to fresh coffee and local art. It’s a great introduction to Hilton Head’s unique offerings.

Hilton Head Farmers Market Shop

Beach House

After getting our fill of local pastries, our Hilton Head itinerary continues at Beach House, where we’ve been offered a room on a complimentary basis. The only boutique hotel on the island’s oceanfront, it has great views of the Atlantic coast.

Hilton Head Beach Hotel

We receive a friendly welcome at check-in, then head to our room. Located on an upper floor, it overlooks the pool area, the famous Tiki Hut bar, and the sand.

Hilton Head Hotel Pool

The interior is full of beach-inspired decor, from the blue walls to the pale accents and nautical art. We love it.

Hilton Head Hotel Room

Biking on Hilton Head

After getting settled into our room at Beach House, we head down to the ground floor to pick up bikes the hotel has reserved for us. We wheel them out onto the sand and go riding down the shore.

We had no idea it was possible to cycle on the beach, but we love feeling the sun on our skin and smelling the fresh Atlantic Ocean air. We could do this all day.

Hilton Head Beach Biking

But more of the island calls, and our Hilton Head itinerary continues as we cycle off the beach and onto the streets in Sea Pines, one of the best parts of the island.

Covering more than 5,000 acres (2,023 hectares), this area has expansive beaches, views of marshes, and maritime forests replete with palmettos, pine trees, and oaks. There are great cycle paths here, and they make it easy and fun to bike on the island.

Hilton Head Biking

Harbour Town

We cycle up to Harbour Town, Hilton Head’s most visited marina. It’s home to a famous red-and-white lighthouse that catches our eyes when we arrive.

We lock up the bikes and start exploring on foot. First we stroll out to the end of a long pier with views over Calibogue Sound and across to Daufuskie Island.

Pier in Harbour Town, South Carolina

Afterwards we walk over to the Harbour Town Lighthouse and have lunch next to it at a restaurant called Quarterdeck. It’s come highly recommended by the General Manager of Beach House, and we can’t wait to try the food.

We head upstairs to the terrace and snag seats overlooking the marina. It’s sunny and warm, and we feel like we’ve hit the jackpot. We order everything from East Coast shrimp and grits to the catch of the day, and it all goes down a treat.

Harbour Town Restaurant

Stoney-Baynard Ruins

Back on the bikes, we continue our Hilton Head itinerary by cycling over to the Stoney-Baynard Ruins. This historic site was once at the heart of Braddock’s Point Plantation, which produced Sea Island cotton.

The main house was built in the late 18th century, and the remains of it, the domestic slave quarters, the plantation kitchen, and a military structure are still visible today. There’s evidence of occupation by Union soldiers during the Civil War as well.

Stoney Baynard Ruins

South Beach Marina

The next item on our itinerary is biking over to the Salty Dog Cafe in South Beach Marina. This famous bar and restaurant sits right above the water, and it’s known for cocktails.

Salty Dog Cafe, South Carolina

We sit at a high table on the big outdoor deck and sip on pina coladas. They’re the only ones I’ve ever had that don’t separate after a while, and they’re all the more delicious for it.

Pina Coladas

When we’re done, we explore the South Beach Marina area. There are a few restaurants here, as well as boutiques, an ice cream shop, and activity outfitters. It’s a pretty place to walk around.

South Beach Marina, Hilton Head

Tiki Hut

By the time we’ve cycled back to Beach House, it’s happy hour. We continue our Hilton Head itinerary by going out to the Tiki Hut. The island’s only toes-in-sand, drink-in-hand bar, it’s a fun place for pre-dinner tropical drinks.

We order a Lava Flow and a Miami Vice, then take seats to enjoy the live entertainment. We sip as the sun turns the sky the colors of our drinks, enjoying the sights and sounds of island life as dusk sets in.

Tiki Cocktails in Hilton Head

The Porch

After finishing our drinks, we head over to The Porch restaurant at Beach House.

We’ve been offered a complimentary meal at this poolside dining establishment, and we tuck into everything from classic fried green tomatoes to seared fish and peach cobbler.

The food is good and our server is warm and friendly. Overall it’s a thoroughly enjoyable experience.

Hilton Head Restaurant

Miniature Golf in Hilton Head

After dinner we hop in the car and continue our Hilton Head itinerary with a trip to Adventure Cove Mini Golf. We can’t visit the island without playing a round of golf, right? And nobody said it couldn’t be of the miniature variety.

We spend an hour dusting off our putting skills and sinking holes in one (well, my boyfriend does). It’s a really fun way to end our first day in Hilton Head.

Hilton Head Mini Golf

Day 2

The next morning our trip continues with a stunning sunrise on the ocean. We throw the windows of our hotel room open and watch as the sky turns from pink to orange and yellow.

Hilton Head Sunrise


Afterwards we pack our bags and enjoy a complimentary breakfast at The Porch at Beach House before checking out. We sit outside by the pool and enjoy fresh omelets with potatoes. It sets us up well for the day.


Stand-Up Paddle Boarding

It’s a good thing, too, because the next item on our Hilton Head itinerary is stand-up paddle boarding. We drive over to Shelter Cove Marina and rent boards from the Outside Hilton Head kiosk.

Shelter Cove Marina, South Carolina

Once on the water, we SUP past the boats and out to Broad Creek. It’s windy, which makes for a challenging paddle, but our efforts are rewarded with dolphin sightings.

It’s a great experience, and we arrive back at the marina feeling like we’ve had a good workout and an enjoyable sightseeing excursion.

Hilton Head SUP

In fact, we’ve had a fun time the whole trip. We get back in the car to drive off the island, regretting we don’t have more time to discover all the other fun things to do on Hilton Head.

Hilton Head Island Itinerary

I hope you’ve enjoyed this Hilton Head itinerary, and that it’s sparked some interest in spending a couple days here yourself.

The island is a great place to visit, and it’s a perfect one to combine with a trip to Savannah and Charleston. Speaking of which, I’m off to the latter now. Stay tuned…

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