Vacation-Ready Itinerary
Charleston’s Islands: Kiawah
Island, South Carolina
Take the stress out of vacation planning with this ready-to-go guide to spending a week in
Kiawah 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!
DAY ONE
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 Glad to Have You mobile app to check-in right on your smart
phone and find helpful tips and area discounts.
6:00pm Visit Fat Hen and get a taste for French Lowcountry cuisine.
Insider Tip: Start with some Fried Green Tomatoes and then dig into the Shrimp
and Grits to get yourself in a southern state of mind.
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 night!
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 for some mid-morning sun. Bring along footballs and sand pails to keep the
kiddos entertained.
12:00pm Wash off your feet, throw on your cover ups and grab some beach cruisers
from Carolina Bike & Beach Rentals. Head to Red’s Ice House for a tasty lunch.
Insider Tip: Their seafood offerings are endless – start with Red’s Rockin’ Crab Dip
before diving into a basket of Fish & Chips.
1:30pm After lunch, peddle around the islands and take in the natural beauty. Get a
cone from The Ice Cream Boat to cool off.
Insider Tip: You can get the bikes delivered right to your rental home for
convenience.
4:00pm Time to wrap up your afternoon of exploring and head back to your vacation
rental to clean up and get ready for dinner.
6:00pm For dinner, keep it casual with a trip to Fischer’s Sports Pub and Grill. Order
some burgers and waffle fries, kick back and enjoy some entertainment.
8:00pm When everyone’s full from a delicious dinner, head home, throw on your
swimsuits and take an evening dip in the pool, if your rental has one.
DAY THREE
8:00am Kick day three off with breakfast on your rental’s deck or balcony. Put out a
light spread of fresh fruit from the local farmers market, yogurt and toast. Brew a fresh
pot of coffee to savor slowly.
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.
11:00am Pack up a picnic lunch and take the family to Night Heron Park. Tour the
Nature Center before renting some kayaks to explore the marshes.
Insider Tip: Stock up on lunchmeat, rotisserie chicken or greens for fast sandwiches
and salads to bring along.
3:00pm After exploring, it’s time to head back “home.” Leave the kids at the rental for a
special night with the grandparents. Then head out early for a date night.
4:00pm Before dinner, make a stop at Firefly Distillery for a tasting before they close
at 5:00pm. Choose from samples of any of the Firefly brands.
Insider Tip: Your tasting is free with our Privileges program!
6:00pm For a fun night out, visit Lokal Seabar. You’ll have trouble deciding on your
order with its mouth-watering menu items and original cocktails.
Insider Tip: Indulge in a comfort food with flair, and order the Lobster Mac and
Cheese.
DAY FOUR
7:30am Head to Java Java for a delicious coffee and some breakfast pastries! Then,
gear up for a day of beach adventures.
9:30am Take to the sea for a Dolphin Encounter with St. Johns Tours. Come face-toface with dolphins, osprey and bald eagles, while you sit back and relax on a boat ride
through the creeks and rivers surrounding the Barrier Islands.
12:00pm When you get back to dock, get some lunch at Pelican’s Nest, a causal spot
with stunning views on Seabrook Island.
Insider Tip: You might even spot some more dolphins over lunch!
2:00pm Visit the Seabrook Equestrian Center for more fun. Enjoy a walking beach or
trail ride – perfect for beginners.
Insider Tip: Reservations must be made in advance, and closed toed shoes and
long pants are required.
4:00pm 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!
6:00pm Prepare an amazing dinner in thanks to your fully-equipped kitchen. If your
rental has a grill too, throw on 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!
DAY FIVE
7:30am Start the morning early with some cereal and coffee in the rental, and then
head out for a day trip to the historic city of Charleston.
Insider Tip: Make your first stop Glazed Gourmet Doughnuts for an extension of
your breakfast.
9:30am Head to the South Carolina Aquarium for exhibits like the Great Ocean Tank
(home to hundreds of fish, including sharks, pufferfish and a 250-pound loggerhead sea
turtle!) You can also tour the Sea Turtle Hospital or engage at the Touch Tank.
12:00pm After spending time with the animals, have lunch at Poogan’s Porch, one of
Charleston’s oldest and most praised eateries.
Insider Tip: Go southern with some She Crab Soup and the Pulled Pork Sandwich.
1:30pm When everyone’s full, explore The Charleston City Market, a popular spot
for everyone who visits the Holy City. You’re sure to find a souvenir with a selection
including paintings, pottery, Charleston’s famous sweetgrass baskets and more.
5:30pm Enjoy dinner at Magnolias before heading back to your rental home. The
restaurant blends traditional ingredients and cooking techniques with modern flair, so
your taste buds are in for a treat.
7:45pm A full day out and about is sure to have everyone tired, so cuddle up in your
rental’s living room to enjoy your favorite movie together. Make sure you grab some
popcorn at the market on your way in.
DAY SIX
8:30am Your last full day at the beach calls for a big breakfast! Get the whole crew
involved in whipping up some blueberry pancakes at the rental, and chat about what
moments you’ve enjoyed best so far.
9:45am Visit The Ocean Course at Kiawah Island and enjoy a round of 18-holes along
the beautifully manicured greens. If golf isn’t your game, visit Urban Nirvana Day Spa
for a restorative morning.
1:00pm For lunch, dine at the golf course at The Ryder Cup Bar. Eat on the open porch
so you can take in ocean breezes and seaside views.
Insider Tip: Order the famous Bagger Burger, in honor of The Legend of Bagger
Vance.
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.
6:30pm Make dinner special at La Tela Pizzeria. They serve a wide selection of
Neapolitan-style pies and Italian cuisine with a kids’ menu for the little ones.
Insider Tip: Order the panna cotta for dessert topped with seasonal fruit!
8:30pm After dinner, take a nice long walk along the beach or visit FortyEight Wine
Bar to sample some wines and local artisan chocolates.
DAY SEVEN
7:30am Sadly, the day has come to leave Kiawah 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.
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
10:00am It’s time to clean up, pack up and head out of your rental. The Glad to Have
You 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.
Map courtesy of Kiawah Resort
PLACES TO STOCK UP
Freshfields Village
Kiawah Island
www.freshfieldsvillage.com
(843) 768-6491
Glazed Gourmet Doughnuts
Charleston
www.glazedgourmet.com
(843) 577-5557
Harris Teeter
Johns Island
www.harristeeter.com
(843) 243-3276
Poogan’s Porch
Charleston
www.poogansporch.com
(843) 577-2337
Johns Island Farmers Market
Johns Island (Saturdays)
www.johnsislandfarmersmarket.com
Magnolias
Charleston
www.magnoliascharleston.com
(843) 577-7771
PLACES TO EAT
Fat Hen
Johns Island
www.thefathen.com
(843) 559-9090
The Ryder Cup Bar
Kiawah Island
www.kiawahresort.com/dining/theatlantic-room/dining-ryder-cup-bar
(843) 266-4085
Red’s Ice House
Seabrook Island
www.redsicehouse.com
(843) 518-5515
Lokal Seabar
Johns Island
www.lokalseabar.com
(843) 764-9027
The Ice Cream Boat
Seabrook Island
www.icecreamboatbohicket.com
(843) 737-5351
La Tela Pizzeria
Kiawah Island
www.latelapizzeria.com
(843) 768-1951
Fischer’s Sports Pub and Grill
Johns Island
(843) 243-0210
Java Java
Johns Island
www.freshfieldsvillage.com
(843) 243-0222
Pelican’s Nest
Seabrook Island
www.discoverseabrook.com/diningvenues-pelicans-nest.php
(843) 768-1244
THINGS TO SEE & DO
Carolina Bike & Beach Rentals
Charleston’s Islands
www.carolinabikeandbeach.com
(843) 747-2453
Night Heron Park
Kiawah Island
www.kiawahresort.com/recreation/
nature-program
(843) 768-6001
Harbour Town Lighthouse & Museum
Hilton Head Island
www.harbourtownlighthouse.com
(866) 305-9814
Firefly Distillery
Wadmalaw Island
www.fireflyspirits.com/distillery
(843) 557-1405
St. Johns Kayaks
Johns Island
www.stjohnskayaks.com
(843) 330-9777
Seabrook Equestrian Center
Seabrook Island
www.discoverseabrook.com/equestrian.
php
(843) 768-7541
Lounge on the beach
South Carolina Aquarium
Charleston
www.scaquarium.org
(843) 577-3474
The Charleston City Market
Charleston
www.thecharlestoncitymarket.com
The Ocean Course at Kiawah Island
Kiawah Island
www.kiawahresort.com/golf/the-oceancourse
Visit Historic Charleston
Urban Nirvana Day Spa
Johns Island
www.urbannirvana.com
(843) 764-9160
FortyEight Wine Bar
Kiawah Island
www.fortyeightwinebar.com
(843) 768-2245
Watch the sunset on the dock
Explore the marsh wildlife
Wyndham Vacation Rentals manages a range of
properties on Charleston’s Islands, from large, private
beach houses to condominiums and townhomes
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.