Your Island Time vacation rental serves as the heart of your reunion—an elegant, spacious property designed to accommodate large groups in style and comfort. Enjoy amenities like a private pool, gourmet kitchen, multiple gathering areas, and close proximity to the beach. Whether you're hosting a welcome dinner on the patio, enjoying movie night with the grandkids, or simply sipping coffee while the sun rises over the dunes, your home-away-from-home is the perfect backdrop for every memory. And with the help of Island Time's Luxury Concierge, planning activities, meals, and special touches is seamless—so you can spend less time coordinating and more time connecting.
Here is a sample itinerary of what your family reunion could look like.
Day 1 – Arrival & Welcome Dinner
Afternoon: Family members arrive and settle into their Island Time home.
Evening: Enjoy a welcome dinner catered by a private chef with Lowcountry favorites like shrimp and grits or a Carolina BBQ spread.
Activity at Home: Family trivia night or custom t-shirt decorating.
☀️ Concierge Tip: Schedule grocery pre-stocking for an effortless arrival.
Day 2 – Beach Day & Bike Exploration
Morning: Beach day! With Island Time, you will receive a credit that can be applied towards beach chairs, umbrellas, toys & so much more. You choose how to apply this credit.
Afternoon: Bike ride along Hilton Head's scenic trails. Your credit can also be applied towards bike rentals.
Evening: Casual dinner at home + family slideshow or photo swap on the big screen.
Day 3 – Water Fun & Relaxation
Morning: Kayaking, paddleboarding, or a dolphin tour (booked in advance during the busier summer months)
Afternoon: Poolside games or family corn hole tournament.
Evening: Island Time can organize an on-site yoga class or massages while kids enjoy a movie night with popcorn.
Day 4 – Golf & Shopping Split Day
Morning Options:
Adults: Golf tee times at Palmetto Dunes or Harbour Town. Or maybe your family would rather play tennis or pickleball.
Teens/Kids: Head to Adventure Cove for mini-golf and arcade fun.
Evening: Sunset photoshoot on the beach followed by dinner out at Hudson's or Skull Creek Boathouse (reservations handled by concierge).
Day 5 – Explore the Island
Morning: Visit Coastal Discovery Museum or go on a guided nature walk. Find the Baynard Ruins in Sea Pines and learn about the history of the Island. Walk through the Sea Pines Nature Preserve which were once cotton fields.
Afternoon: Take a private boat charter to see the Island from a totally differently perspective. Chances are you will see dolphins, too!
Evening at Home: Family-style cookout with lawn games and s'mores under the stars.
Day 6 – Just for the Kids / Adults' Night In
Daytime: Arrange a
fun-filled kids' day with crafts, scavenger hunts, and pizza. Hire a local childcare expect to come to the house and watch the kids so you can have an adults only afternoon.
Adults: Enjoy a wine tasting or private mixology session at the house.
Evening: Everyone gathers for a family awards night or karaoke party!
Day 7 – Farewell Breakfast & Departure
Morning: Depending on your check out time and travel plans, be sure to gather together as a family one last time. Have breakfast together with easy grab and go foods that can hit the road with you, or make packing up easier.
Planning a reunion with multiple generations can be overwhelming—but not with Island Time's Luxury Concierge. They can:
The best part.... our Luxury Concierge service is no charge when you book directly with us. Book early to ensure availability and make your family reunion one they'll never forget.
