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7 Day Travel Itinerary: Hilton Head Island

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Harbor Town, Hilton Head, South Carolina
Harbor Town, Hilton Head, South Carolina

This 7 day Working Joe Travel Itinerary explores Hilton Head Island in South Carolina. Most everything mentioned at this family-friendly vacation destination can be done moderately priced.

Hilton Head Island is like heaven and key lime pie. It is a dreamy escape with an unexpected kick. The island is sectioned into a number of self-contained ‘plantations,’ each with its own small center and personality. In developed areas there are well-landscaped hotels, restaurants, and stores for every taste. In undeveloped areas, there are beautiful and surprising natural vistas to explore.

Marshland on Hilton Head Island, South Carolina Travel
Marshland on Hilton Head Island

Wooden boardwalks traverse sand dunes along 12 miles of beach. With virtually no rocks or seaweed, the shore line is one long sandy highway. Traveling down it, on one side there is the hypnotic rhythm of the waves, on the other gorgeous seaside cottages. Inland, wooded paths wind through marshes revealing an abundance of birds, turtles and alligators. Our 7 day itinerary will acquaint you with the best things to do on Hilton Head Island.

Relaxing by the Beach Hilton Head Island, South Carolina Travel
Relaxing | Hilton Head Island

Hilton Head Island handles its contrasts well. Here, the atmosphere is both bustling and low key. There is an abundance of water sports and activities to take part in, but the wide beaches and blue skies invite you to do nothing at all. Or, at the very least, park your vehicle and travel by beach bike.

Hilton Head Island Travel Itinerary At-A-Glance, South Carolina

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Biking on Hilton Head Island

This is Randy and I’s favorite activity on the island. With over 60 miles of public paths and trails there are few places that cannot be accessed by bike. Rental bikes are affordable and accessible. Check out half-day E-Bike rentals here.

Free biking maps are available at information centers and stores. The bike paths on some plantations are private so check your route before heading out. Bike riding on the public beaches is a popular activity here. There is mile upon mile of hard packed sand to cycle across. Inland, the flat, often shaded terrain makes for enjoyable exercise.

Biking on Hilton Head Island | Hilton Head Island Things to do
Biking on Hilton Head Island

Hilton Head Island Beaches

With over 12 miles of public beaches you can be as up close or far away from others as you desire. There are thousands of units for rent on Hilton Head Island. Put the work into finding an affordable unit on the beach (or within walking distance). g

You won’t regret it. If you really cannot get a place on the beach, look for a location with easy access to one of the public beaches with a large parking lot (Coligny, Driessen, and Fish Haul Beach Park). Or, stay at a plantation that has a private beach club you can use (Sea Pines, Leamington, Port Royal).

Forest Beach, Hilton Head Island Things to do, South Carolina Travel
Forest Beach, Hilton Head Island

Hiking on Hilton Head Island

Cyclists share the public paths and trails with walkers and joggers. In addition to these routes, there are 14 miles of marked gravel trails at the Pickney Island National Wildlife Refuge and 50 acres to explore at the Audubon Newhall Nature Preserve (both located on the island). Both sites are great for hiking, biking, and birdwatching. Bring your camera to catch shots of alligators, turtles, deer, cranes, and many migratory birds in action.

Watersports on Hilton Head Island

So many things to try… Boat trips (zodiac, kayak, catamaran, sail boat, cycle boat, fishing boat, pirate boat, dolphin boat, and ferry), surfing, parasailing, and more. Public marinas dot the island. We are partial to Broad Creek, but there are quality facilities close to every plantation. Here is a sampling of some water activity tours on Hilton Head Island:

Estuaries of Hilton Head | 7 day travel itinerary hilton head island
Estuaries of Hilton Head

Other Activities on Hilton Head Island

On the island you can golf, tour wildlife, horseback ride, mini-golf, or visit an adventure center with rope courses and zip lining. In addition, there are day trips to Savannah (by boat, touring company, or car), Gullah heritage tours, and historic forts and plantations within an hour driving distance to the island. Here is a sampling of some of the great activities that are available:

Water Sports on Hilton Head | Hilton Head Island Things To Do, South Carolina Travel
Water Sports on Hilton Head

Shopping and Restaurants on Hilton Head Island

For a seaside feel check out Harbor Town, South Beach and Shelter Cove. For souvenirs try the Coligny Plaza. To shop in earnest head to the Tanger Outlet just over the bridge on Rt. 278. Our favorite restaurants are all seafood: Skull Creek, Hudsons, the Salty Dog, the Old Oyster Factory, and the Crazy Crab.

The Salty Dog Cafe in Harbor Town | Hilton Head Island Travel Itinerary
The Salty Dog Cafe


Day 1: Check In. Harbor Town

Unpack and go for walk around your resort. Rent a bike and buy groceries. Spend the afternoon by the pool or amble along the beach. At sunset, take a ride to Harbor Town. Circle the path around the marina to view the yachts up close. Walk the wharf and climb to the top of the red and white striped lighthouse as the sun goes down. Then shop the seaside mall and finish your evening with drinks and dinner at one of Harbor Town’s restaurants.

Harbor Head Lighthouse, Hilton Head Island, South Carolina
Harbor Head Lighthouse

Day 2: Biking – Beach – Seafood

Have coffee and light breakfast, then pack for a bike ride. Check the tide and wind direction. If it is not high tide, plan your route to end with a beach ride with the wind to your back. On the first leg of the trip, follow an inland bike route that pedals into the wind. At your half-way point, make your way to the beach and finish your loop with a ride along the coast. It’s spectacular. After lunch, ready for an afternoon at the beach (or by the pool).

Beach Bike Riding on Hilton Head Island | Hilton Head Itinerary, South Carolina
Bike Riding on the Beach

This evening treat yourself to a sit-down seafood dinner. Try one of our favorite restaurants (listed under restaurants above) and order a regional favorite – she crab soup, bacon hush puppies with maple butter, or a pimento spread – yum!


Steer clear of paths that follow the Cross Island Parkway and Route 278. Both of these routes are crowded, heavily trafficked, and require the rider to frequently cross intersections and commercial driveways.

Eating Dockside | Restaurants on Hilton Head, South Carolina Travel
Eating Dockside

Day 3: Water Sport and Shelter Cove

Try a new water sport or activity. One trip we did a dolphin boat ride. We crammed into a small boat and rode through the marshes and out onto open water. We saw many dolphins, some who swam alongside the boat. It was a low-key tour, but a memorable day. Another time we took a ferry to Daufuskie Island, rented a golf cart and toured the island. Let your interest guide you. After some pool time later in the day, take a ride to Shelter Cove and spend the evening getting to know the restaurants, shops, and things to do in this area.

Broad Creek Marina, Hilton Head Island Itinerary
Broad Creek Marina

Day 4: Sightseeing in Savannah

Savannah is close and such a cool city it would be a shame not to go. You can get there from Hilton Head Island by ferry boat, through a touring company or by driving (it’s about a 50-60 minute drive). In Savannah you can tour the historic district and Victorian neighborhoods, shop in the pedestrian-only City Market, or spend an afternoon in the shops and bars of River Street. There are many types of tours throughout the day and evening. If the city does not appeal to you try a Gullah heritage tour, a wildlife tour through one of the preserves, or a trip to a nearby fort or plantation.d

Fountain at Forsyth Park, Savannah Georgia | Hilton Head Itinerary
Fountain at Forsyth Park, Savannah

Day 5: Shopping and South Beach

Sleep in, go out for breakfast and spend the morning (or day) shopping (see Shopping above for location suggestions). Spend the afternoon by the pool or beach. End your day with a trip to South Beach where you can get dinner and explore this seaside village.

South Beach, Hilton Head Island Itinerary, South Carolina
South Beach, Hilton Head

Day 6: Repeat of Day 2

Biking, beach, and seafood.

Day 7: Pack and Check Out

See you soon! Laura and Randy

For more information on travel itineraries to the southeastern United States read our articles on:

Laura & Randy | Hilton Head Island, South Carolina Travel
Laura & Randy | Hilton Head Island


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