Where are we talking about?

Hilton Head, South Carolina

Known for its Atlantic beaches and golf courses, Hilton Head is a resort island that sits in the Lowcountry region of South Carolina.

When should we go?

Best: May-September 

While the island is beautiful year-round, it's quiet, beautiful and peaceful during the wintertime and the holidays are very festive (here). We love to go in the summer to soak-up the warm, beach weather. It will take you a bit of travel to get there, but I’m telling you that it will be worth it when you’re sitting in a chair on the beach, watching the sunset with a drink in your hand.

What’s the best way to get there?

If you want to minimize your travel time, both United and American fly into the Hilton Head (HHH) airport, from Washington, D.C., Charlotte, and Chicago. As of May 23, 2019 Delta will begin flying direct from Atlanta. Alternatively, you can fly on any major airline into Charleston or Savannah. Hilton Head is only a 2-hour drive from Charleston and less and an hour from Savannah. Plus the Savannah airport is really manageable and incredibly easy to navigate.

Rtip: If you’re looking to explore a bit more of the South consider adding Spring Island, Charleston or Savannah to your Hilton Head itinerary. You can read our Roam Guide to Charleston here.

How do you get around?

Having a rental car can be helpful if you are traveling with family or a large group, and if you plan to go out regularly. Lyft and Uber do operate on the island, and there are also multiple cab companies, if you don’t want to rent a car. Depending on which part of the island you stay, there is a large network of pedestrian and bike paths and many bike rental companies. I recommend The Sea Pines Resort Bicycle Shop and Pelican Cruiser, both we’ve rented from with success.

Rtip: Make sure you book your bicycles in advance, especially during the summer!

Where should we stay?

Harbour Town and its lighthouse sit at the southwest tip of the Island, and the airport sits at the north end, near the gated residential community of Hilton Head Plantation.

The Sea Pines Resort, where my family stays, occupies the southern third of HHI and is regarded by many, as the best part of the island. The resort has several rental options available. Additionally Booking.com offers a few homes and condos for rent at Sea Pines, but VRBO has way more to options to consider. Whatever accommodations you choose, Sea Pines is a wonderful resort full of bike paths, activities, and shops. One of the joys of staying on the Sea Pines Property is the easy biking access to places like Lowcountry Produce Market & Café or C’est Bon. Every morning you can head to either (or both – they’re located right next to one another!) for coffee, tea, fresh orange or grapefruit juice, and smoothies and don’t forget a glazed yeast doughnut or cheddar biscuit Lowcountry Produce. Sea Pines also offers three incredibly scenic golf courses to play. Even if you aren’t a golfer, you’ll enjoy having a meal on the large porch at Fraser’s Tavern overlooking part of the golf course and lagoon.

Ritp: Also located within Sea Pines you’ll find multiple Marriott’s properties (Heritage Club, Harbour Club and Monarch), the perfect option if you’re a traveler who loves Marriott.

Located a bit north of Sea Pines you’ll find Palmetto Dunes, an oceanfront resort with three golf courses, a marina, tennis center, and lagoon where you can go kayaking or canoeing. Depending on the size of your group, they have condo and vacation home rentals on booking.com as well.

Across William Hilton Parkway from Palmetto Dunes lies another resort, Disney’s Hilton Head Island Resort. It’s a wonderful place to stay with young kids, families, or anyone who loves a bit of Disney magic. They offer multi-room villas or a deluxe studio room to rent, and there are two casual dining options on site. For fun in the sun, head on over to Disney’s Beach House, which is accessible by bike paths or regular shuttle service.

Rtip: If you are looking for a more intimate stay with less than 200 rooms (and you’re willing to splurge) the Montage Palmetto Bluff is incredible.

What should we do while we’re there?

For some socially-distances outdoor time, Pinckney Island National Wildlife Refuge is a nice place to explore and observe wildlife such as deer, alligators, and birds. Boat tours, private fishing charters, and water sports (parasailing, anyone?) are other activities that will give your group or family something fun to do. There are many options out of Shelter Cove Marina and Harbour Town. 

One of my family’s favorite activities is to go on a two-hour guided kayak tour through the salt marshes with Outside Hilton Head. It’s a fun way to gain a different perspective of the island, and if you’re lucky you’ll see a wide variety of wildlife. In addition to kayaking, Outside Hilton Head can set you up with boats, paddleboards, surfing, fishing, and kids programs.

Rtip: Go with the early morning activity times before the heat and humidity really kick up for the day.

Whatever you do, make your beach time more enjoyable with a beach chair and umbrella, body boards, and kayak rentals from Shore Beach Service! In the afternoon, when you need some shade, hop onto your bike and ride over to The Sea Pines Forest Preserve! There you can go fishing in one of the lakes (a permit is required), explore the marshes and get up close with wildlife as you stroll along boardwalks through the Vanishing Swamp or Old Lawton Rice Field. Just keep in mind you have to pay a fee at Sea Pines if you are not staying there.

Once you’ve left the beach for the day, head on down to Harbour Town, located within The Sea Pines Resort. Browse through a wide variety of shops, enjoy some time on the Harbour Town Playground, admire the boats docked in the yacht basin, and then take in a sing-along performance with Gregg Russell, a Harbour Town institution. You also can’t miss the chance to climb to the top of the Harbour Town Lighthouse where you’ll be rewarded with amazing views.

“I have such great memories of Gregg Russell. He entertains under a beautiful old tree by the lighthouse! I sang on his stage when I was young and years later, so did my daughter.” - Roam Guide, Carrie Sinclair

Located across the Calibogue Sound from the south tip of HHI, Daufuskie Island is a unique place to go exploring when you need a break from the beach or pool (surprising, I know, but it can happen!). Daufuskie Island is only accessible by boat or passenger ferry from HHI or Bluffton, making it an adventure just to get there! Very few cars are allowed on the island, so plan ahead and make a reservation for a golf cart from one of the many tour companies that operates on the island. Hop into a golf cart and zoom around the island to see numerous historical sites, visit an art gallery, have lunch at Old Daufuskie Crab Company, and then take a nature walk along the beach before you catch the ferry back to Hilton Head.

Rtip: Pat Conroy’s book The Water is Wide is based on his experience teaching in the two-room schoolhouse on Daufuskie Island. Read this award-winning book before or after your visit for a deeper look into what life was like for the residents.

What should we eat in Hilton Head?

Always our first stop on the island, Fiesta Fresh is a no-frills, casual spot for lunch or dinner that is beloved by locals and visitors alike. You truly can’t go wrong with anything that you might order from their menu, but some personal favorites are the fish wrap, cheese dip, and the churros. While you wait for your meal, enjoy the complimentary chips and salsa bar.

If you still have room in your stomach after Fiesta Fresh, walk to the nearby Hilton Head Ice Cream. I’m partial to the peach pecan and watermelon sherbet with dark chocolate chips in it, but chocolate cayenne or cherry vanilla might be the flavors to tempt you. My dad and Aunt are first generation Italian-American, so gelato is a well-loved treat in my family. Surprisingly, you can find this sweet treat on the island as well, at  Nonna Marie’s. It’s made fresh daily, and they offer vegan, dairy free, and gluten free options.

Let’s continue to talk sweets with Hilton Head staple, Signe’s Heaven Bound Bakery & Café they are known for homemade pastries, breads, and pies. You must order a slice of chocolate pecan pie, and take some peanut butter and cowboy cookies with you for an afternoon snack. For breakfast you can’t go wrong with their shrimp and grits, polenta, or deep-dish French toast, and their crab cake tart is one of my all-time favorite dishes.

A vacation should be a vacation for all, so get out of the kitchen and order from Local Pie, the only Neapolitan-style wood-fired pizza on HHI, or the family-run Dough Boys Pizza which has a varied selection of specialty subs in addition to their other offerings. Both restaurants offer a gluten-free crust option for their delicious pizzas. 

Another casual, locally-focused takeout option is Chow Daddy’s. They serve up fresh and yummy salads, tacos, burgers, and bowls at their two locations on Hilton Head (one in Sea Pines) and one in Bluffton. Gluten-free options available as well. 

For those nights when you want to cook up some local seafood, plan your menu around the fresh offerings from Barnacle Bill’s Fresh Seafood Market, located towards the North end of the island. Get there early if you want the largest selection of options, or go closer to lunchtime and enjoy a variety of local food trucks that are set up behind Barnacle Bill’s. If you just want to dine on local seafood instead of cook it, then head to Hudson’s Seafood on the docks for the freshest catch and the most incredible low country sunsets on Skull Creek.

If you are likely to cook at home I recommend specialty foods shop, Michael Anthony’s Market. Their recently expanded market has a wonderful selection of Italian staples and easy prep takeaway foods such as fresh and dried pastas, fabulous frozen gnocchi, sauces, oils, cheeses, and meats. They have a full service restaurant next door, which I highly recommend for dinner once you’ve washed off all of the sunscreen for the day. Keep in mind you can also call the market 24 hours in advance and place an order to pick up an antipasti platter or lasagna. You can also sign-up for a cooking class at Michael Anthony’s Cooking School. I love to learn new recipes and the school’s classes cover a wide range of topics. Keep in mind, they fill-up quickly, so book ahead.

If you eat a vegetarian diet or are in the mood for something lighter that won’t weigh you down for your afternoon tennis game, look no further than Delisheeyo. The Sweet Buddha Bowl is a great breakfast option for when you’re out and about, and their salads and wraps are perfect for lunch. I always get the So-Cal wrap and customize it with gluten-free rice paper and add beets (bring on the veggies!). Don’t forget to add a fresh juice, volcanic lemonade, or tart frozen yogurt. Call in your order ahead of time to minimize wait time.

Rtip: Be sure to check out Salty Dog. They always have live music and the parents can hangout while the kids dance around.  The performer usually hands out glow necklaces and the ice cream shop is delicious.

Where should we go for a drink?

Both located at The Sea Pines Beach Club, the beachfront bar at Coast and the Ocean Lounge (which is located on the second floor of the Beach Club), make for memorable drinking experiences. They offer wine, beer, specialty cocktails, and frozen drinks (that can be made without alcohol). The beachfront bar is more casual, while the Ocean Lounge has a resort-wear dress code and is the perfect spot to celebrate something special.

Where can we do a little shopping?

If you’re in Sea Pines and need to purchase new reading material, a greeting card, or a small gift, look no further than By Hand, Ink. This gem of a bookstore is small in size but contains an excellent selection. 

Nothing says full relaxation mode like a beautiful new bathrobe to snuggle in while you drink your morning coffee. Fashion Court, Inc. is a lingerie store in Harbour Town with a great selection of nightgowns, pajamas, and robes, as well as baby clothes.

If you unpack your suitcase and realize that you’ve forgotten to pack a swimsuit or flip- flops, you can find replacements at Quiet Storm. Located in Coligny Plaza – a bustling center with shops, restaurants, and a Piggly Wiggly grocery store – Quiet Storm carries accessories and clothing for women, men, and kids. They also sell skimboards, surfboards, and skateboards if you decide you want to lean in to your new island persona and practice a new skill!

If you happen to find yourself with rainy weather during your stay on HHI and need toys or games to keep the kiddos entertained, Kidz for Life Toys & Games at Harbour Town is the place to go. Kids of every age will enjoy this cute shop.

Rtip: Taking place in the plaza of The Shops at Sea Pines Center is a local farmer’s market, held Tuesdays beginning in March. Find local artisans, produce, BBQ, seafood, etc. 

What should we bring with us?

For sure you’ll need a cheeky cooler bag, SPF lip balm, a great beach read and a packable sun visor!

Rtip: Look online ahead of your trip at Little Fish Boateak. If it were me I’d buy some of her chic, colorful and textured earings, handmade in Hilton Head.

Tell us something we don’t know?

Who doesn’t love taking long walks along the beach, looking for shells? However, shells are much more than just something pretty to collect. Did you know that shells have a long, intertwined history with Hilton Head Island? Go explore the Sea Pines Shell Ring which dates back almost 4,000 years and is the oldest known archaeological site on HHI. Additionally, shells, specifically oyster shells, were a key component in tabby, a type of building material that was often used between the late 1500s and 1850s in the coastal Southeast. Take a beautiful bike ride through Sea Pines to the tabby ruins of Stoney-Baynard Plantation (which some say is haunted!).