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Hilton Head, SC— 2 Day Travel Guide + Itinerary

Hilton Head is a beautiful foot shaped island located in the southern tip of South Carolina. It's notoriously known for being a relaxing coastal beach town, perfect for those laid back family vacations. If you're a golfer then it's even more of a reason to visit because the island is a golfer's paradise— there are over 24 golf courses and it's home to quite a few famous golf tournaments every year.

We spent two full days on the island and actually got to see one of my good friends tie the knot while we were there!

Anyways, if you're looking for a family friendly beach vacation spot for your next trip, Hilton Head is a fantastic option. Just be sure to rent a car if you go because everything is pretty spread out and you'll be able to explore a lot more!

PS, if you're new here my name is Stephanie and I'm CT based content creator sharing what to wear and where to wear it. Be sure to follow me along on my other social accounts for even more content and a big dose of my everyday life —@sugaredstilettos for all the outfit inspo + @sugaredtravels for even more travel content.

Here's a summary of what you will find in this Hilton Head itinerary travel guide in case you want to jump ahead!


The Omni is ideally located right on the beach making it truly the perfect home base to soak up some sunshine amongst some spectacular views. It's a great option for those looking for an ultra relaxing vacation due to the convenience of so many incredible on site amenities. The resort has two restaurants, three cocktail bars, a spa, three pools, access to the beach, and have on site rentals for the beach and bike usage. For more information and for booking click here.

I think the biggest highlight has to be the easy access to Palmetto Dunes beach. There is a path running directly from the hotel and takes about 3-4 minutes to get to. Did I mention the beach is absolutely beautiful and has spectacular sunrises?

Palmetto Dunes Beach— Hilton Head, South Carolina

We stayed in one of their studio suites, which is their base room I might add, and it was incredibly spacious and cozy. It comes fully equipped too— there is a king bed, sleeper sofa, mini kitchen, dining table, and a private balcony that offered beautiful views of the grounds and water.

One last huge perk— the resort is pet friendly and your fur baby will most certainly get the royal treatment during their pupcation. We brought our frenchie, Harwich, with us and he was greeted with treats, his own bowls, and a plush cozy bed!


Located in Shelter Cove Harbour this little bakery was next level delicious. They have such an extensive selection of pastries, desserts, and coffee making it the perfect spot for a breakfast by the marina. I am still day dreaming about their croissants if I'm being honest.

Cute little breakfast or lunch spot that's located in Harbour Town Pier. This spot has both indoor and outdoor seating and you can find something for everybody on their menu. We ordered the chicken and waffles and they were SO good.

Please do yourself a favor and add this spot to your list. Rain or shine the Hilton Head Distillery is such a fun thing to add to your itineraries. They do everything from distillery tours and tastings to signature cocktail classes. There is also an on-site cocktail bar that whips up some insanely good and unique spins on classic cocktails. We had so much fun here and it was easily one of our favorite things that we did! You can find a fill list of their classes and tours here.

They also have a gift shop where you can take home all the goods you sipped on during your visit if you're not ready to part ways with them. The Mexican Chocolate and Bananas Foster were easily my two favorites!

Located on the banks of Skull Creek with beautiful waterfront views Skull Creek Boathouse is a must if you're on the island! They have both indoor and outdoor dining, but if you can get a table outdoors do so because the views are amazing. They have an extensive menu featuring a full sushi bar and a really fun cocktail list.

If you're a fellow seafood lover you're going to absolutely LOVE it here. Do yourself a favor and try their ceviche and sushi!

PS.. they're pet friendly on the patio!

Known for their fresh ingredients sourced from local farms and waters their seasonal menu is sure to leave a lasting impression on you. Every single thing we ate down to our dessert was packed with so much flavor. We ate outside on their heated patio and listened to live music as we dined. I highly recommend booking a dinner reservation here if you're in the area.

Definitely try the pimento cheese fries and stuffed eggs to start they were SO good.

Expect a wait here, but this popular spot is a good option to grab a mid day pick me up!


Harbour Town Pier and Shops

There are multiple restaurants, tons of shopping to be done, and a beautiful view of both the Marina and Lighthouse!

Beach Day

This one is a no brainer. The beaches here, as I mentioned above, are so beautiful and if you're staying at the Omni, easily in reach! The pictures below speak for themselves. PS.. catch a sunrise if you can!

Stoney Baynard Ruins

These grounds date back to the 18th century and tell the legend of the Stoney and Barnard families. As you walk through the ruins you're walking through the very location that planters and Confederate troops walked on centuries ago.

You can take a self guided tour or sign up for a guided tour trough the Nature Center in Harbour Town. However, I think a self guided tour is all you need!

Go for a Bike Ride

With over 60 miles of bike paths to explore and so much scenery to soak up going for a bike ride to cover some ground is a great way to go explore.

Enjoy the Nightlife!

There are so many good options to check out during your stay, but a few top picks are the Black Marlin Hurricane Bar, The Boardroom, Poseidon's, or the Tiki Hut!

Day Trips

If you're in town for long enough and have time to carve out a day trip or even spend some additional time somewhere else Savannah (45 min) and Charleston (2hrs) are both within driving distance. We actually headed to Savannah for our next stop— check out my Savannah Travel Guide here!

I hope this was helpful! Be sure to follow along for more!

Be sure to follow me along on my other social accounts for even more content and a big dose of my everyday life —@sugaredstilettos for all the outfit inspo + @sugaredtravels for even more travel content.


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