Hilton Head Travel Guide


I’ve been meaning to share a Hilton Head travel guide for quite some time since we typically visit there twice a year.  Usually, we head down once in the spring and then the last week of August when the summer crowds start to thin out.  This year, we decided to spend Christmas break down there which we’ve done once before.  Christmas time is ideal because the island is decorated quite beautifully, it’s not too crowded and the weather is still warm enough to enjoy lots of outdoor activities.  Essentially, there is no bad time to vacation in Hilton Head.  The sub tropical temperatures ensure a mild winter (December, January and February are normally in the low to mid sixties) so you can bike along the beach, play golf, tennis, kayak, fish….you name it….Hilton Head has it all.  This travel guide will lean more towards those with small children since that’s my current scenario but I will throw in a few suggestions for those who are single and read to mingle!

For starters, if you’re not within driving distance (and you’re not completely insane like we are who drive from New York with four kids), the best airport to fly into is in Savannah which is a short 40 minute drive.  There are flights that go directly to Hilton Head which has a small airport but I would imagine you’d have to transfer in a major hub plus the convenience will probably cost you.  Since Savannah is so close, it’s ideal for day trips.  I’d highly recommend a trolley or walking tour because it’s steeped in so much history and the guides are quite informative.  It’s a beautiful old city that is divided up into squares but it does get pretty hot and humid in the summer so I would opt to visit Savannah during the cooler months.  Charleston is about a two hour drive in the opposite direction.  It’s also a gorgeous old southern city (a little larger and a bit more cosmopolitan than Savannah) with plenty to see and do.  We’ve done the day trip there as well but the four hours in the car can be a bit much.  Now that you know how to get there, let’s turn our attention back to Hilton Head where I’m going to break it down by where to stay, eat, and things to do.

Where To Stay: 


Hilton Head is divided up into several gated communities call “plantations.”  We’ve stayed in different ones over the years and honestly, it’s hard to choose a favorite.  However, here are the ones I would recommend:

1. Palmetto Dunes: 

Palmetto Dunes is an oceanfront community that encompasses a blend of large resorts, private homes and condos. There is a lagoon that runs through this plantation where you can fish, kayak and boat.  There are also miles of bike trails throughout the community as well as several golf courses and a plethora of tennis courts.  We have rented a two story townhouse both times we’ve stayed in this plantation.  It’s about a ten minute bike ride to the beach (or a two minute car ride).  It borders a golf course and has a big pool for the kids so we love this particular rental which is in the Turnberry community.  Whether you’re looking for a private home or a condo, my suggestion is to look on VRBO .  We’ve always had luck with them.

As for hotels, there is a huge Marriott directly on the ocean as well as an Omni.  The Omni looks especially incredible and it’s definitely a place I’d love to stay with my husband for a romantic getaway (#oneday).

In addition to the restaurants at both hotels, there is another smaller restaurant on the lagoon called Alexander’s that has received great reviews.  I definitely want to try it out the next time we visit.

2. Sea Pines: 

Sea Pines is seriously so picturesque, you’ll feel like you’re in a dream.  There’s Spanish moss and palmetto trees everywhere….the forest literally leads right up to the beach.  There are also bike paths galore, Lawton Stables, golf, tennis and two towns on opposite ends of the plantation (a trolley will take you around the plantation if you don’t want to drive).  The two towns are South Beach Marina which has so many cute shops and a few restaurants right on the water and Harbour Town which is similar but a little larger and it has a lighthouse that you can climb to the top of (it’s quite a hike…I was panting by the time I got to the top).  Both are ideal for grabbing drinks and catching a sunset, enjoying a meal and an ice cream cone afterwards and strolling around the harbor while simultaneously browsing in a few shops.

There is a Marriott right on the ocean (perfect for families) as well as the Inn at Harbour Town  which is in the center of everything.  I think this hotel is better suited for couples since Harbour Town is not ocean front but rather overlooking a marina and a golf course.  Plus, you can walk to dinner and all the shops.

Of course, there are a ton of private homes you can rent as well as condos so there’s something for everyone here.  We stayed in Sea Pines with our extended family one year and the location couldn’t have been better.  We were a stones throw away from the ocean and a five minute bike ride to South Beach Marina.

3. Port Royal: 

Port Royal is located in the center of the island so it’s convenient to shopping, restaurants, and the airport.  However, once you enter the gates, it’s so serene and peaceful.  The bike paths are beyond beautiful and of course they border yet another golf course.  There are two main hotels on the ocean, the Marriott and a Westin.  The Westin looks amazing plus it has a covered pool (perfect for rainy days) in addition to the larger ocean front one.

We stayed in Folly Field a couple of times which isn’t technically part of Port Royal but it’s adjacent so we biked through there everyday.  Folly Field has several condos and private homes to rent and it has a wonderful public beach which was within walking distance from where we stayed.

Where to Eat: 


We usually go grocery shopping the first day we get there and cook most of our meals but it’s become a tradition to treat the kids to one meal out and that’s always at the Salty Dog in South Beach Marina.  There’s an outdoor seating area and a bar (and during the colder months, there’s a fire pit with benches surrounding it) so we like to grab a drink, let the kids run around and listen to the live music while we wait for a table.  There’s also an ice cream shop adjacent so naturally, we head over there afterwards.

This past time we visited, we took the kids out for a New Year’s Eve dinner at Bucco’s in Shelter Cove Harbor (which is a waterfront community right across from Palmetto Dunes).  The service was fantastic and the meal was even better.  I got a pasta pomodoro topped with goat cheese (#beyond).  Another night, my husband and I were able to get out for a drink at Ela’s which overlooks the harbor and is right across from the Disney Resort.  It’s ideal for outdoor seating and taking in a sunset.

The next time we go back, I want to try out The Skull Creek Boathouse , The Sage Room, and Java Joe’s for their coffee and pastries.

What To Do:


There is a ton to do in Hilton Head.  It just depends on whether you’re the outdoorsy, adventurous type, prefer a good book and a beach chair, or if you’re there to take advantage of the numerous golf courses.  While I’m more of the ride my bike and relax at the beach/pool kind of person, my husband loves to take the kids kayaking, fishing, canoeing, etc.  And of course, he doesn’t mind sneaking in a game of golf here and there.  I highly recommend renting bikes and bringing sneakers for walks along the beach and all the paths.  There’s also tennis everywhere so if you own a racket, you should definitely bring one.

Aside from enjoying the beach, the lagoons, biking and golf, there is a mini golf place which we always go to.  There are also the stables I mentioned in Sea Pines where there are animals and pony rides as well as the Coastal Discovery Museum which is an unbelievable, old southern home on a huge piece of land (a definite must see).   There are dolphin cruises which I’m dying to go on next time as well as a day excursion to nearby Dafauskie Island.  Since there are so many activities to list, you can read about these and more right here.

If you want to venture off the island for the day, you can check out Old Town Bluffton which is a short drive and is the cutest little town dotted with antique shops and restaurants.  Further away is Palmetto Bluff, which is a gated community about 40 minutes away.  It’s a picturesque southern town located on the May River.  Grab some lunch at Buffalo’s  or dinner at the River House Restaurant.  I would love to escape to the Montage for a long weekend with my husband.  It looks so quintessentially southern and relaxing….definitely on my to do list!

And so there you have it!  I’m sure I’m missing something but I’m speaking from our experience up to this point so I’m sure as our kids get older, my travel guide will evolve!  Feel free to email me with any questions or recommendations.  I would be more than happy to offer any advice.  Hilton Head has definitely become our home away from home and I’m already looking forward to returning this summer.