HILTON HEAD ISLAND
- Annette Brooks
- 3 days ago
- 3 min read
BEACHCOMB WITH YOUR BESTIES ON THIS SOUTH CAROLINA GEM
BY ANNETTE BROOKS

Pack your bags, gather your girlfriends, and head to a coastal paradise that promises sunshine, laughter, and unforgettable adventures. From pristine beaches to charming boutiques, luxury spas, world-class golf courses, and mouthwatering cuisine, Hilton Head Island, South Carolina, offers everything you need to bond, relax, and indulge.
DAY 1: WELCOME TO PARADISE
As soon as you cross the bridge onto Hilton Head Island, the salty breeze and live oaks draped in Spanish moss welcome you to a haven of Southern charm. With picturesque beaches and a relaxed pace, Hilton Head is the perfect place to recharge and reconnect with friends.
First stop? Your fabulous accommodations. Whether you choose a luxury oceanfront condo, or a cozy Airbnb tucked into one of the island’s lush communities, there’s a perfect spot for your group. Bonus points if it comes with a pool or patio for morning coffee and late-night chats under the stars!
Next, make a list of provisions and order pickup from one of the island’s gourmet grocers unless you feel like roaming the aisles. Include a selection of prepared entrees and sides in your order to share in the first evening while you catch up and settle in.

DAY 2: BEACH BLISS AND LOCAL FLAVOR
There’s nothing like starting your day with friends over coffee, mimosas, and fresh fruit. Then grab your sunscreen and head to Coligny Beach, one of the island’s most popular white-sand beaches. Prefer a quieter vibe? Check out Singleton Beach or Driessen Beach Park. Bring snacks or, better yet, splurge on a luxury picnic or grazing board from Board and Basket (BoardAndBasketHHI.com).
Freshen up after your beach day and prepare for a culinary adventure. Hilton Head is a foodie paradise. Check out longtime favorites like Crazy Crab for crab legs with a water view or Hudson’s Seafood House on the Docks for fresh oysters. Pair your meal with chilled wine and toast to an amazing trip.

DAY 3: ADVENTURES AND RETAIL THERAPY
Start your morning kayaking or paddle boarding on Skull Creek, where you might spot dolphins and herons. Prefer a slower pace? Opt for a guided nature tour or boat ride through marshlands to view wildlife like osprey or stingrays.
Next, enjoy a leisurely lunch at Low country Produce Market & Café, which is famous for its pimento cheese sandwich and tomato pie. Then, dive into retail therapy. Explore Coligny Plaza, Shelter Cove Towne Centre, and The Village at Wexford for coastal-inspired treasures, local gems, and chic finds.
Wrap up the day with a sunset boat cruise to witness Hilton Head’s golden-hour skies. The views are Insta-worthy, and the memories — priceless.
DAY 4: EXPLORATION AND SPA TIME
After breakfast, rent bikes to explore the island’s 60+ miles of paved trails. Pedal through lush landscapes and visit Harbour Town with its iconic red-and-white lighthouse and charming shops.
Then, get pampered at one of Hilton Head’s luxury spas. Indulge in a massage, facial, body wrap, or Reiki session to rejuvenate your senses and promote relaxation.
Finish your day with a final stroll on the beach after dinner. Reflect on the laughter, shared sunsets, and strengthened bonds from your getaway.

Day Trip to Historic Savannah
Hilton Head Island is a serene coastal getaway, but just a short 45-minute drive away lies Savannah, Georgia, a city brimming with Southern charm, history, and a culture all its own. It’s the perfect complement to Hilton Head’s laid-back vibe.
Start by exploring Savannah’s historic squares, each lined with centuries-old oak trees draped in Spanish moss. Don’t miss Forsyth Park, a picturesque spot for photos or a leisurely stroll. Dive into the city’s storied past with a visit to landmarks like the Cathedral of St. John the Baptist or the Mercer-Williams House.
For lunch, savor authentic Southern cuisine at one of Savannah’s renowned restaurants, such as The Olde Pink House or Mrs. Wilkes’ Dining Room. If you’re there on a Sunday, try the Grey Restaurant for brunch.
End the day shopping along River Street or taking a scenic riverboat cruise before returning to Hilton Head’s tranquil shores.
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