Multigenerational Area Guide
Activities
Explore
What to see and do around the island as a family.
Pirate’s Island Adventure Golf
Two 18-hole courses add up to 36 holes of pirate-themed mini golf at Pirate’s Island Adventure Golf, a multi-year TripAdvisor Travelers’ Choice winner. You’ll putt over wooden bridges, alongside flowing streams, and beneath cascading waterfalls while following clues to hidden treasure inside a
pirate’s cave.
Kayak & Paddleboard Tours
Guided kayak and paddleboard tours take your family onto Broad Creek and the island’s tidal salt marshes, where the water stays calm and the pace stays easy. Local outfitters lead tours for every skill level, and tandem kayaks let a grandparent and grandchild share a boat.
Lawton Stables
Trail rides wind past lakes, forest, and open paths across more than 600 acres of protected Lowcountry land. Every horse is cared for with pride, and the guides match each rider with a horse that fits their experience. Little ones who aren’t ready for the trail can walk through the on-site petting zoo to meet pigs, llamas, donkeys, sheep,
and more.
Biking Through Sea Pines
Sea Pines’ network of leisure trails makes biking the easiest way to see the community together, with flat, shaded paths that suit training wheels and beach cruisers alike. Ride to Harbour Town and its red-and-white-striped lighthouse, roll out to South Beach for ice cream, or loop through the Sea Pines Forest Preserve to spot alligators sunning on the banks.
Featured Family Event
Shelter Cove HarbourFest Fireworks
Tuesday nights during summer · Shelter Cove Harbour & Marina
Every Tuesday night from early June through mid-August, Shelter Cove Harbour & Marina hosts HarbourFest, a summer tradition families have built their island weeks around for decades. Arrive early to stroll the waterfront promenade, take in the marina views, and settle in for live music by the water. Kids can line up for face painting, balloon artists, and bounce houses set up right by the docks, while parents and grandparents grab a bench and watch the boats come in.
Dinner is easy, with waterfront restaurants, quick bites, and ice cream all a short walk away. Once the sky turns dark over Broad Creek, the fireworks launch and their reflections double the show across the water. HarbourFest is free and open to the public, which makes it one of the simplest evenings to plan for a group of any size. Bring a blanket or a few beach chairs and claim your spot along the harbor before sunset. It’s a natural way to close out a beach day, and for many families it becomes the night they come back for, summer after summer.
A Summer Night for Every Age
Toddlers on shoulders, teenagers along the seawall, and grandparents with the best seat on the bench: HarbourFest has a spot for everyone. The show starts once the sky is fully dark, so plan dinner at the harbor and let the evening build.
From a HarbourFest regular
“We have gone for 30+ years... We went early, had dinner, and enjoyed Shannon Tanner. My kids are adults now and my grandchildren went for years... It is fun and quite an event... a great show and worth the effort.”
Gather Together · Island Favorites
Dining
A few local favorites for the whole family to enjoy, from classic diners to local seafood cuisine.
Big tables, shared plates, and something on the menu for every generation.
From the guide
“Cool spot for a casual dinner, especially the outdoor patio with lights. Plenty of room for the kids to run around... A relaxed spot for a family meal.”
Hilton Head Diner
Hilton Head Diner pours thick, old-fashioned milkshakes and builds towering sundaes the way a classic American diner should. Roomy booths and a big menu make it an easy stop for three generations with three different appetites.
The Bank
The Bank pairs a main kitchen of crowd-pleasing favorites with a lineup of outdoor food trucks, so everyone at the table can order something different. Its in-house brewery keeps easy-drinking craft beers, rotating favorites, and seasonal releases on tap. The string-lit patio gives kids room to roam while the adults linger over one more round.
The Crazy Crab
The Crazy Crab has been serving Lowcountry recipes on Hilton Head Island since 1986, with every entrée prepared to order. Its Alaskan snow crab legs have won local awards for years. In summer, live music and wide water views turn dinner into the main event of the evening.
Family Beach Day · Island Favorites
Beaches
Families cherish Hilton Head Island’s coastal haven for its pristine, broad stretches of sun-drenched sand and calm, gentle Atlantic waters.
Hard-packed sand and gentle surf make a beach day easy for all ages.
Coligny Beach
Coligny Beach Park pairs hard-packed sand for beach bikes with calm Atlantic water that’s easy for swimmers of every age. Rocking chairs, shaded gazebos, outdoor showers, and free Wi-Fi give grandparents a comfortable place to settle in for the day. Coligny Plaza sits right across the street with more than 60 local shops, beach bars, and casual restaurants, so lunch never means packing up the car.
Folly Field Beach
Folly Field Beach trades the crowds for wide stretches of soft sand, reached by a wooden boardwalk that winds through the dunes. Paved parking, outdoor showers, restrooms, and seasonal lifeguards make it an easy mid-island pick for families with little ones. Come early for sunrise, catch a few waves with the skim boarders, or walk the shoreline together at low tide.
South Beach
At the southern tip of Sea Pines, South Beach pairs a quiet stretch of sand with a New England–style fishing village built around the original Salty Dog Cafe. South Beach Marina rents kayaks and paddleboards, runs dolphin-watching cruises, and keeps boutique shopping and casual waterfront dining steps from the shore. Finish the afternoon on the boardwalk with an ice cream cone and a view across Calibogue Sound.
Local Tip · Plan Around the Tide
Hilton Head’s tide can swing six to eight feet, and low tide leaves the widest, firmest sand of the day. Check the tide chart before you head out: low tide is the best time for bikes, tide pools, and long walks with the little ones.
Select Experience
Salty Dog Sunset Cruise
Salty Dog Sunset Cruise · South Beach Marina
Sunset Cruise
Calibogue Sound at golden hour
Food & Drink
Onboard kitchen and full bar
Double Decker
63-foot catamaran, two levels
The Island From the Water
A Salty Dog sunset cruise leaves South Beach Marina aboard a double-decker catamaran and heads out onto the calm water of Calibogue Sound. From either deck, the Lowcountry coastline opens up in every direction, from Harbour Town Lighthouse to the salt marshes and Daufuskie Island across the sound. Kids and grandparents alike can scan the waves for Atlantic bottlenose dolphins swimming alongside the boat, while pelicans and shorebirds glide over the marsh. Between island-style tunes, the crew shares stories about local marine life and the area’s coastal ecosystem.
Good to Know Before You Board
The onboard kitchen serves Salty Dog favorites like steamed shrimp, crab cakes, and quesadillas, with a full bar for the adults and juices and soft drinks for the kids. As the sun drops, the water turns gold and pink, and you’re back on shore in time for dinner. Tickets must be purchased in advance, prices vary by season, and summer sailings sell out quickly, so book as soon as your dates are set. Arrive early to walk South Beach Marina and grab an ice cream before you board.
From a recent guest
“We love the sunset cruise! Perfect length, kind staff, always great views... I’ve been about 3-4 times, every time we saw dolphins and the sunsets are absolutely amazing as is the music on board...”
Book Direct · No Platform Fees
Signature Generational Stays
A few of the homes we recommend for a family reunion island visit.
14 Juniper
Inside, the home feels warm, open, and naturally welcoming. Expansive windows fill the interiors with sunlight while vaulted ceilings and coastal-inspired finishes create an airy atmosphere throughout the space. Multiple living areas allow everyone to spread out comfortably while still staying connected, making the home ideal for larger groups and multi-generational stays.
3 Urchin Manor
Escape to a luxury oasis just a few minutes' walk from Bradley Beach at this six en-suite retreat, built to comfortably host up to 18 guests across multiple generations or several small groups under one roof. Breathtaking ocean views, a private pool and spa, and access to a private boardwalk straight to the sand set this home apart, while thoughtful touches like a luggage elevator and dedicated great rooms make every stay feel effortless.
71 Dune Lane
A luxurious coastal retreat tucked just one row off the beach in North Forest Beach. Thoughtfully designed with elevated finishes, open-concept gathering spaces, and a stunning private pool oasis, this home offers the perfect blend of sophistication and relaxation. Spend your days lounging beside the heated pool and spa, enjoying friendly ping pong tournaments in the game garage, and creating unforgettable memories with family and friends.
114 Sandcastle Court
Lagoon views from every floor and a game room built for endless fun set the tone at this 4,500 square foot retreat in Sandcastles By the Sea, one of Hilton Head's newest gated communities. This six en-suite home welcomes up to 16 guests plus your furry dog, and comes with a free golf cart on site, a handy way to get to and from the beach, just a half mile away.
73 Dune Lane
Wake up to the sound of the Atlantic and step onto the sand in just 20 steps at this oceanfront escape in North Forest Beach. Breathtaking ocean views, a private pool and spa, and an outdoor kitchen set the stage for effortless coastal living, while spacious, beautifully designed interiors give every guest room to gather and unwind. This escape delivers the multi-generational family vacation guests dream about.
9 Juniper
An exquisite oceanfront escape spanning over 5,226 square feet in the heart of South Forest Beach. With direct beach access via a private boardwalk, eight luxurious en-suite bedrooms, and a separate guest house offering added privacy, this sanctuary accommodates up to 19 guests and was designed for connection, comfort, and unforgettable group gatherings.
Looking for Something Else
Host & Home manages homes across Sea Pines, Palmetto Dunes, Forest Beach, Shipyard, Folly Field, Singleton Beach, and beyond — from cozy villas to oceanfront homes built for the whole family. Bringing a bigger crew? Neighbors 71 and 73 Dune Lane can be booked side by side for up to 27 guests. Connect with our local team and find the stay that fits.
Ready to Book
Plan Your Next Stay
Host & Home offers a higher standard of stay: comfort, care, and craft; thoughtfully prepared for your arrival. Our team excels in providing high-end customer service and takes a proactive approach to ensure every detail is meticulously handled.
Drawing from hands-on experience in the 5-star hotel, real estate, and vacation rental industries, we’ve taken best practices to the next level, delivering a stay that feels effortless, local, and genuinely well cared for.
Everything Handled Before You Arrive
This is where a thoughtfully hosted stay makes the difference — more than just a place to sleep for the week. With Host & Home, the details are handled before you ever arrive: local support, a well-prepared home, and a Hilton Head experience that starts long before check-in.