Vacation-Ready Itinerary

Hilton Head Island, South Carolina

3:00pm Head to your vacation rental home! Stop by a local grocery store to stock your kitchen for the week.

Insider Tip: Use the Wyndham Vacation Rentals Hilton Head Island mobile app to check-in right on your smart phone. You can even order groceries online using your Privileges Program discount!

8:00pm After taking a long walk on the beach, return to your vacation rental for some much deserved relaxation. Start your vacation week off right with a family movie or game night!

6:00pm Visit Skull Creek Boathouse for some tasty renditions of Lowcountry favorites.

Insider Tip: Order the peel & eat shrimp and crab dip for an appetizer and try their fresh catch of the day to kick off your week on “island time!”

DAY ONE

DAY TWO

8:00am With the great selection of area groceries, markets and bakeries, whipping up a delicious breakfast in your rental home is easy as pie! Make some eggs and bacon for a yummy start.

9:30am Pack up the kids, fill your coolers with snacks and drinks, and head to the beach or on-site pool if your rental has one for some mid-morning sun. Bring along footballs, volleyballs or a kite for even more fun on Hilton Head Island’s hard packed sand!

12:00pm Wash off your feet, throw on your t-shirts and head to Stu’s Surfside Subs for some of the island’s best subs made with fresh bread.

Insider Tip: The Calibogue Sub along with a tasty local beer is the way to go!

1:30pm Around the corner, you’ll find shopping at The Coligny Beach Shopping Center. Hit the local boutiques to browse classically coastal artwork, t-shirts and jewelry. Then sneak over to the Tiki Hut for local music, happy hour and volleyball.

6:00pm For your second dinner on the town, go to Poseidon Coastal Cuisine. This oceanfront option offers everything from seafood pasta to steaks and sandwiches. Plus, you can’t beat the views of the Pass from their outside seating area.

8:00pm When everyone’s full from a delicious dinner, head across the street and grab a cone from Kilwins, the best ice cream parlor at Shelter Cove!

Take the stress out of vacation planning with this ready-to-go guide to spending a week in Hilton Head Island, South Carolina. Strike the perfect balance between downtime and “go”

time with our day-by-day itinerary, followed by a directory in the back.

Don’t forget to share your vacation photos using #vacationdifferently!

4:00pm Time to wrap up your afternoon shopping and head back to your vacation rental to clean up and get ready for dinner.

8:00am Kick day three off with some breakfast out. Our friends at Watusi have a wonderful selection of mouth-watering dishes that will wake you right up!

Insider Tip: Try the homemade biscuits and sausage gravy to put everyone in a southern state of mind.

DAY THREE

9:30am Have some fun with the kids in your rental’s pool, if there’s one on-site or access to a community pool. Grab a float and relax while everyone splashes around.

12:00pm Take a break and whip up some lunch in the rental. Sandwiches are an easy meal to prep and clean.

Insider Tip: Stock up on lunchmeat, rotisserie chicken or greens for fast sandwiches and salads.

6:00pm Take the family to Hudson’s Seafood House on the Docks for dinner. This casual, oceanfront eatery features delicious seafood and plenty of fun for everyone.

Insider Tip: Indulge in locally caught seafood and steak with a delicious side of hushpuppies!

5:00pm After exploring, it’s time to freshen up and get ready for dinner! Head back to the rental and have the folks at Outside Hilton Head pick up the gear.

DAY FOUR

7:30am Head to the Palmetto Bay Sunrise Café for a jumbo stack of pancakes! This family-focused breakfast operates daily during the summer. Enjoy eggs, bacon and pancakes while you watch the line cooks prepare the meals.

9:30am Head a few minutes south to the Tanger Outlets in Bluffton. This outdoor outlet mall has favorites like Polo Ralph Lauren, Sunglass Hut, Nike and Carter’s. Stock up on back-to-school essentials or treat yourself!

1:30pm Grab some grub on your way back to the beach at Giuseppe’s, the island’s favorite local pizza joint.

5:00pm Prepare an amazing dinner in thanks to your fully-equipped kitchen. If your rental has a grill too, throw on some steaks or chicken and create some delicious side dishes inside.

7:30pm Grab some after-dinner refreshments (in plastic cups of course!) and head down to the beach with the crew for a memorable walk during sunset.

Insider Tip: Don’t forget your camera!

3:00pm After a full day of activities, it’s probably time to unwind on the couch or enjoy some ZZZs on the balcony or deck before dinner. Spend an extra hour pampering yourself before a great night in!

1:30pm Hilton Head Island is home to the Harbour Town Lighthouse & Museum, Sea Pines’ iconic candy cane-striped lighthouse that lets guests climb to the top to take in the island’s beautiful views. Then peddle around town on some bikes from Outside Hilton Head.

8:00pm When everyone’s full and happy, leave the kids with the grandparents back at the rental and head to the south side of the island, dubbed the “Barmuda Triangle,” for live music and tasty drinks.

1:00pm Stop into a local favorite and enjoy some food at The Quarterdeck Waterfront Dining. This on-the-water eatery has strong drinks, juicy burgers, flatbread pizzas and sandwiches.

DAY FIVE

10:00am Get everyone ready and embark on a new kind of adventure. See our friends at Zipline & Aerial Adventures of Hilton Head Island for a thrilling morning the whole family will love!

1:30pm After your sky-high adventure, rest up and re-fuel. Lunches can be easy by serving leftovers from the meal you cooked the night before, or use the lunchmeat and salad fixings you have on hand.

6:00pm As the weather cools, get cleaned up and ready for dinner. Make the trip to San Miguel’s Mexican at Shelter Cove for a delicious night.

Insider Tip: Try the margaritas – a summertime staple and best on the island.

2:30pm With all the vacation fun you’re having, you almost forgot why you came to Hilton Head Island in the first place: THE BEACH! Grab some boogie boards and footballs, and hit the sandy surf.

7:45pm Big meals are sure to put everyone in a cozy state of mind, so cuddle up in your rental’s living room to enjoy your favorite movie together. Make sure you grab some popcorn at the grocery store on your way in!

DAY SIX

8:00am Your last full day at the beach calls for a big breakfast! Head to Skillets Café & Grill for a wide selection of breakfast sandwiches, delicious pastries and fresh roasted coffee.

9:45am Visit one of the great area golf courses, such as Harbour Town Golf Links (home of the RBC Heritage), and enjoy a round of 9-holes or more along the beautifully manicured greens. Club rentals are available, and a driving range can help you brush up on your skills or teach the basics.

6:30pm Make dinner special at The Sage Room. This spot offers the freshest seafood, the best artisan ingredients and an amazing atmosphere.

Insider Tip: Get a private table or gather around the chef’s table and enjoy watching them prepare your food!

8:00am Now that your body has adjusted to “island time,” sleep in a bit. Start the day off easy by fixing breakfast sandwiches and fruit to take with you as you bike around the island.

8:30pm After dinner, take a nice long walk down Coligny Beach and catch the sunset over the waves.

4:30pm Before your last vacation dinner, get ready back at your rental, and enjoy some happy hour time on the balcony or deck. Whip up summer cocktails, Shirley Temples and cheese trays, and take in the island views.

DAY SEVEN

7:30am Sadly, the day has come to leave Hilton Head Island. But don’t fret! The fun is far from over. It’s time to whip up all the breakfast food that’s left in the fridge and get ready for the day.

12:00pm It’s time to clean up, pack up and head out of your rental. The Wyndham Vacation Rentals Hilton Head Island mobile app lets you simply get in the car and hit “check-out” when you’re ready. But you may want to visit the local office to secure the property for your vacation next year!

Insider Tip: Current guests have first right of refusal on their home for the same week next summer.

12:15pm On your way out of town, enjoy some fresh seafood one last time! Go see the good people at The Salty Dog Café for raw oysters, Cajun style Po-Boys and a tall glass of sweet tea to put the perfect cap on your vacation.

8:45am Once you clear out the kitchen, head to the beach for some last-minute sun or bring the kids to the pool and wear them out before the drive or flight back home.

Skull Creek BoathouseHilton Head Island www.skullcreekboathouse.com (843) 681-3663

Hudson’s Seafood House on the DocksHilton Head Island www.hudsonsonthedocks.com(843) 681-2772

Poseidon Coastal CuisineHilton Head Island www.poseidonhhi.com(843) 341-3838

KilwinsHilton Head Islandwww.kilwins.com (843) 785-2727

San Miguel’s Mexican Hilton Head Island www.sanmiguels.com(843) 842-4555

Publix Hilton Head Island www.publix.com (843) 842-2632

Kroger Hilton Head Island www.kroger.com(843) 842-0540

Harris Teeter Hilton Head Island www.harristeeter.com(843) 785-6185

Farmers Market BlufftonThursdaysBlufftonwww.farmersmarketbluffton.com (843) 415-2447

Giuseppe’s PizzaHilton Head Island and Bluffton locationswww.giuseppispizza.comHilton Head Island: (843) 785-4144Bluffton: (843) 815-9200

Stu’s Surfside Subs Hilton Head Island (843) 686-7873

Tiki HutHilton Head Island www.tikihuthhi.com (843) 785-5126

WatusiHilton Head Island www.hiltonheadcoffeeandyogurt.com (843) 686-5200

Palmetto Bay Sunrise CaféHilton Head Island www.palmettobaysunrisecafe.com(843) 686-3232

Skillets Café & GrillHilton Head Island www.skilletscafe.com(843) 785-3131

The Quarterdeck Waterfront DiningHilton Head Island www.quarterdeckhhi.com(843) 842-1999

The Sage RoomHilton Head Island www.thesageroom.com(843) 785-5352

The Salty Dog Café Hilton Head Island www.saltydog.com(843) 671-2233

PLACES TO STOCK UP

PLACES TO EAT

The Coligny Beach Shopping CenterHilton Head Islandwww.colignyplaza.com (843) 842-6050

Harbour Town Lighthouse & Museum Hilton Head Island www.harbourtownlighthouse.com(866) 305-9814

Tanger OutletsBluffton www.tangeroutlets.com(843) 837-5410

Outside Hilton Head Hilton Head Island www.outsidehiltonhead.com(800) 686-6996

Zipline & Aerial Adventures of Hilton Head Island Hilton Head Island www.ziplinehiltonhead.com(843) 682-6000

Harbour Town Golf LinksHilton Head Island www.seapines.com/golf(800) 732-7463

THINGS TO SEE & DO

Enjoy a beach day

Play a round of golf

Grab dinner downtown

Browse the local shops

Wyndham Vacation Rentals manages a range of properties in Hilton Head Island, from large, private beach

houses to condominiums and villas.

Visit WyndhamVacationRentals.com to find your rental.

#VacationDifferently with us.

Wyndham Vacation Rentals does not endorse any of the activities described or mentioned. It is the individual’s responsibility to investigate the safety and suitability of any activity. Wyndham Vacation Rentals expressly denies any liability for engaging any activity and for using any guide, vendor, or service provider

that may be mentioned or described in this itinerary.