The Lawson Family standing on the beach during a Kiawah Island vacation.

Kiawah Island Activities - Weekend Itinerary

 

Are you ready for unforgettable itinerary filled with Kiawah Island activities weekend? We’re Shawn and Jeanette, locals who have called this area home since the late ’90s. While a weekend is too short to experience everything, this itinerary will guide you through the Lowcountry’s top highlights. And when you’re ready to relax after your adventures, there’s no better place to unwind than one of our boutique vacation rentals. Each property is just five minutes or less from the beach, offering top-of-the-line comfort, cleanliness, and thoughtful touches like fresh flowers and personalized welcome notes to make your stay truly memorable.

Day One: Bike Kiawah Island

Overview

On day one, you’ll explore Kiawah Island the best way possible—by bicycle. With over 10 miles of bikeable beach and 30 miles of scenic bike trails, renting a bike is a must to experience the top Kiawah Island activities. We’ve mapped out a route that will take you through the island’s rich history, wildlife, and forests, finishing the day with a ride along the beach, giving you a well-rounded view of everything Kiawah has to offer.

Before you Begin:

  • Rent your bikes in advance at BikeKiawah.com.
  • When overtaking, notify fellow bikers or walkers by saying “Passing on your left”.
  • Note that electric bikes and golf carts are not allowed on the path.

Morning: Explore Kiawah

  • The Shoolbred Cemetery (101 Shoolbred Ct)
    Ride along the Kiawah Parkway using the island’s main bike path. Located in Rhett’s Bluff Area, this historic cemetery was owned by James Shoolbred, Esquire, the first British consul to the United States in 1790. Read more about James Shoolbred here
  • Marsh Island Tower (262 Governors Dr)
    Off Governor’s Drive, this tower offers panoramic views of Kiawah’s marshes and the Kiawah River. Look out for crabs darting in and out of their burrows as you explore the surrounding nature path.
  • Eagle Point Landing (222 Eagle Point Rd)
    Located just past the wooden bridge on your right, Eagle Point Landing provides a view of the Ravenel Bridge in the distance. Take a moment to soak in the peaceful sounds of nature.

Lunch: Ryder Cup Bar

  • Lunch at Ryder Cup Bar (1002 Ocean Course Dr)
    Located at The Ocean Course clubhouse, the Ryder Cup Bar offers scenic views. Don’t miss the compass rose ceiling connected to the rooftop weathervane. If the weather is pleasant, sit outside to enjoy the ocean breeze.

Afternoon: Ride Along the Beach

  • Beach Ride Back (Take Boardwalk 40)
    After lunch, take your bike boardwalk 40 to access the beach. Ride along the shore back to your accommodations with the wind at your back. Watch families and children playing in the sand as you enjoy the ride.

Evening: Shopping and Dinner

  • Freshfields Village (149 Village Green Ln)
    Make a quick stop to browse local shops before dinner.
  • Dinner at Hege’s (275 Gardners Cir)
    End your day with a delicious french meal at Hege’s. Be sure to make a reservation in advance by calling (843) 768-0035.
A lone bicycle stands on the smooth sands at the end of the beach on Kiawah Island, symbolizing peaceful solitude.
A serene marshland path on Kiawah Island, inviting nature lovers for a scenic biking experience.
Two people cycling over a wooden bridge surrounded by marshland at Eagle Point.

Day Two: Explore Charleston

Overview:

Your second day takes you to historic Charleston, just a short drive from Kiawah Island. After enjoying Kiawah Island’s activities, spend the day exploring Charleston’s markets, historic sites, and art galleries. Along the way, stop at some of our favorite restaurants for a taste of Charleston’s cuisine. End the day with a sunset walk at Waterfront Park, overlooking the harbor.

Before you Begin:

  • Charleston is a 45 minute drive from Kiawah Island, so leave early to make the most of your day.

Morning: Shopping and Historic Sites

  • The Charleston City Market (188 Meeting St)
    Start your Charleston adventure at the historic City Market, located at Meeting and Market Streets. This market offers a wide range of local goods, perfect for picking up souvenirs like Charleston Benne Wafers, antiques, and local crafts. Plan to spend about 1-2 hours browsing the stalls.
  • Washington Park (80 Broad St)
    Take a peaceful stroll through Washington Park, located behind City Hall. This historic park features monuments to Confederate soldiers and Charleston’s history. Relax under the shade of oak trees while reflecting on the city’s past. Read more about Washington park here.

Lunch: Hyman’s Seafood or Aaron’s Deli

  • Lunch at Hyman’s Seafood (215 Meeting St) or Aaron’s Deli (213 Meeting St)
    Hyman’s is famous for affordable seafood, offering broiled to fried dishes. Aaron’s Deli provides lighter deli sandwiches if you prefer something quick and casual. Avoid the midday rush by arriving early or late.

Afternoon: Historic Sights and Art Galleries

  • The Pink House (17 Chalmers St)
    Stop by the Pink House, one of Charleston’s most charming historic buildings, now housing a small art gallery showcasing local artists. Don’t forget to visit the top floor for a unique view of the city. Learn more about the Pink House here.
  • The Old Slave Mart (6 Chalmers St)
    Just across from the Pink House, you’ll find The Old Slave Mart, an important site to reflect on Charleston’s history. Learn more about the Old Slave Mart here
  • Old Exchange and Provost Dungeon (122 East Bay St)
    A must-visit for history enthusiasts, this site offers tours of the dungeon and exhibits on Charleston’s colonial and Revolutionary War history. Learn more here
  • Rainbow Row (83-107 East Bay St)
    No visit to Charleston is complete without a stroll down Rainbow Row. These brightly colored homes are a symbol of Charleston’s architectural charm. Take a few photos as this is one of the most iconic spots in the city. Learn more here.

Evening: Dinner and Sunset Walk

  • Dinner at Magnolia’s (185 East Bay St)
    Treat yourself to a delicious Southern meal at Magnolia’s. Make sure to reserve a table in advance, as it’s a popular spot for both locals and tourists.
  • Waterfront Park (1 Vendue Range)
    Before heading back to Kiawah, take a sunset walk at Waterfront Park, offering stunning views of Charleston Harbor where the Ashley and Cooper Rivers meet. The park’s fountain is a great spot to relax and reflect on your day.
Pineapple Fountain in Charleston, South Carolina.
pineapple fountain in Charleston sc
Aerial view of Charleston, South Carolina, at sunset.

The Perfect Kiawah Island Vacation Rental

As you plan your visit to the Lowcountry, consider staying with us at Kiawah Island Getaways. We are a boutique, family-run vacation rental business with a focus on “quality over quantity.” Because we’re small, we take extra care with every property. You’ll arrive to a beautifully staged home, with the lights on and everything ready for you to enjoy your stay. It’s the small touches that make us stand out. All of our properties are either oceanfront or just a short walk from the beach, offering easy access to various Kiawah Island activities.

Interior of a professionally decorated vacation rental at Kiawah Island.
A bright, luxurious bedroom at Ocean Blue by Kiawah Island Getaways featuring elegant bedding, large windows with natural light, and decor that showcases how to make a perfect bed.
The Ocean Blue at Seascape - Kiawah Island Getaways Vacation Rental
Picture of Jeanette and Shawn

Jeanette and Shawn

Founders of Kiawah Island Getaways, a luxury vacation rental company with over 20 years of experience serving guests on Kiawah. See our 5 star reviews here and our availability here. Book your rental today!

The Ocean Blue at Seascape

Upscale Kiawah Island Vacation Rentals

Kiawah Island Getaways offers you a boutique collection of the most comfortable, fully-vetted rentals on Kiawah Island.

Guarantee a relaxing and comfortable vacation by staying with Kiawah Island Getaways!

Each of our properties have been vetted and are top-of-the line in decor, comfort and cleanliness to meet our high standards and yours.

You’ll be delighted with the unexpected items we provide. You can expect fully stocked kitchens, entertainment options and much more!

The special touches will make your entire family smile – fresh flowers, a personalized welcome note and eggs from our own back-yard family coop when you arrive.

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