With its seemingly endless summer adventures, Hilton Head Island is undeniably among the best places to visit. Recently ranked #11 in Travel + Leisure’s World’s Best Awards and one of the top-booked summer vacation spots in the U.S., it is clear why this island is where sights are seen and memories made.
Spend your days lazing around 12 miles of pristine sandy beaches or enjoy the endless world class entertainment available from golf and racquet sports to biking, hiking, and even wildlife and preserve exploration. If you are looking for a calm getaway, or an adrenaline fuelled holiday, our Hilton Head Island Summer Guide will ensure you experience the island like a true local.
Hilton Head Island Beaches
Hilton Head’s beaches are legendary. Coligny Beach is one of the island’s most frequented due to its family-friendly amenities, restaurants, and commodious access to the beaches. If you are looking for less noise, want to bask in the warm waters of the Atlantic and watch soft shades of sparkling sands during sunrises or sunsets, Mitchelville Beach and Fish Haul Beach Park might be the perfect fit for you.
On the Water Activities
Make a splash with water sports galore! Go paddleboarding, kayaking through calm lagoons, or try parasailing for stunning views of the island. Book a dolphin-watching cruise, charter a deep-sea fishing trip, or enjoy a romantic dinner cruise as the sun dips below the horizon.
Biking & Hiking Trails
Hilton Head is a Gold Level Bicycle Friendly Community with more than 60 miles of multi-use trails. Rent a bike and cruise through shaded paths, or hike the Sea Pines Forest Preserve and Pinckney Island National Wildlife Refuge. These scenic routes offer glimpses of wildlife, marshes, and native plants.
Golf Courses & Tennis Facilities
Tee off at some of the best golf courses in the country, including Harbour Town Golf Links, home of the PGA Tour’s RBC Heritage. Tennis and pickleball lovers will appreciate world-class facilities like the Van Der Meer Tennis Center and Palmetto Dunes Tennis & Pickleball Center, offering clinics, lessons, and round robins.
Most of our villas are located in Hilton Head Beach and Tennis Resort, where guests can enjoy on-site access to both tennis and pickleball courts, making it easy to play a quick match or schedule lessons while on vacation.
Horseback Riding
Saddle up for a peaceful trail ride at Lawton Stables, where you can trot through shaded paths of the Sea Pines Forest Preserve. It’s a fun, memorable way to connect with nature and enjoy the island’s natural beauty.
Family Fun on Hilton Head Island
There’s no shortage of family-friendly fun! Spend a day at Adventure Cove playing mini-golf and arcade games, enjoy an interactive experience at the Coastal Discovery Museum, or explore the Pirates of Hilton Head cruise for a swashbuckling good time. The island also features waterparks, playgrounds, and outdoor movie nights.
Arts, Culture & Historic Sites
Explore Gullah heritage at the Gullah Museum of Hilton Head, tour Mitchelville Freedom Park, or catch a show at the Arts Center of Coastal Carolina. Hilton Head also boasts art galleries, historic churches, and local festivals celebrating Lowcountry culture.
👉 Want to dive deeper into the island’s rich African American heritage? Discover Gullah Traditions on Hilton Head Island and learn more about the vibrant culture that continues to shape the Lowcountry today.
Health, Wellness & Luxury Spa Days
Treat yourself to a relaxing spa day at Heavenly Spa by Westin or FACES Spa, offering massages, facials, and full-body treatments designed to help you unwind and rejuvenate.
For a deeper dive into Hilton Head’s spa scene and top spots to unwind, check out The Ultimate Relaxation Guide: Spa Retreats on Hilton Head for more recommendations.
Shopping in Hilton Head
Shop everything from upscale boutiques in Harbour Town and Shelter Cove Towne Centre to souvenir shops and art markets. Don’t forget to stop by local farmers markets for unique Lowcountry finds.
For more great recommendations on where to shop, be sure to read Where to Shop: 6 Must-Visit Spots in Hilton Head Island.
Eating Out on Hilton Head Island
Indulge in fresh seafood, Southern cuisine, and international flavors. Here are our top picks:
Top 3 Restaurants:
- Skull Creek Boathouse – Famous for waterfront dining and local seafood.
- Michael Anthony’s – Elegant Italian dining with exceptional wine pairings.
- Hudson’s on the Docks – A Hilton Head institution with fresh catches daily.
Dinner Cruises:
- Spirit of Harbour Town Dinner Cruise – A relaxing, scenic meal on the water.
- Vagabond Cruise – Enjoy a Lowcountry boil and sunset views.
Late Night Venues:
(Image Source: Hilton Head Island)
- The Jazz Corner – World-class jazz and gourmet dining.
- Tiki Hut – Beach bar vibes with live music.
- The Boardroom – Cocktails, dancing, and lively fun into the night.
Events & Activities This May
Make your summer kick-off even more exciting with these upcoming May events:
- Music & Taste on the Harbour – May 1st, 12th & 18th at Shelter Cove. Outdoor concerts, food vendors, and fun for all ages. Pet-friendly!
- 46th Annual Mayfest – May 10th in Bluffton. A hometown favorite featuring over 130 vendors, live music, pie-eating contests, and more.
- Hilton Head Art Festival – May 23rd–25th at Shelter Cove. Stroll through fine art exhibits, enjoy local entertainment, and shop from artists across the region.
- More Top Events: Check out comedy shows, sunset paddle tours, and special Memorial Day Weekend happenings around the island.
Luxury Properties with Oceanside Properties
Make your summer unforgettable by staying in one of our top vacation rentals:
- Seaside Villa 288 – Enjoy coastal views, beachside relaxation, and direct beach access.
- Tennis Villa F18 & other Tennis Villa Units – Perfect for tennis and pickleball enthusiasts, with easy access to on-site pros, lessons, and round robins.
These units are part of Hilton Head Beach and Tennis Resort, so guests enjoy all the resort amenities including pools, playgrounds, on-site dining, and pristine beach access. With 2 bedrooms and 2 baths, these villas are perfect for families or groups of friends.
Where to Stay in Hilton Head
Ready to plan your summer 2025 vacation to Hilton Head Island? Oceanside Properties offers a wide variety of beachfront and resort-style vacation homes for every type of traveler – whether you’re escaping for a weekend or staying for the season.
Book your stay with Oceanside Properties today and discover the perfect balance of adventure, relaxation, and Southern hospitality this summer on Hilton Head Island!
