48 Hours on Hilton Head Island: A Relaxed Weekend Itinerary

By Hilton Head Insider

Hilton Head Island is the kind of place where the salt air hits you the second you cross the bridge, and suddenly, life slows down to a more manageable pace. You don't need a week to find your footing here on America’s Favorite Island®, you just need a plan that balances adventure with Lowcountry calm. Whether you’re here for the championship golf or just a quiet stretch of sand, we’ve put together a 48-hour weekend itinerary that cuts straight to the best of Island life.

What You’ll Learn in This Article

How to plan a 48-hour Hilton Head Island weekend so it feels relaxed, not rushed
Where to go for Harbour Town views
How to make the most of the Island’s bike-friendly pathways and beach time in one afternoon
Which spots to try for sunset seafood and easy outdoor dining
How we do our part to protect baby sea turtles (and how you can do yours)
How to plan for dolphin and wildlife viewing on the water
Where to go and when to visit for world-class golfing

Your Itinerary At a Glance

Day 1: Harbour Town views, exploring bike trails, beach time, sunset seafood dining, starlit shores
Day 2: Fresh pastry, time on the water, a Lowcountry lunch, golf (or a relaxed alternative), one last toast

Day One: Lowcountry Landmarks & Starlit Shores

Morning: Harbour Town From Above

After you check in and drop your bags, head to The Harbour Town Marina and Lighthouse. This icon of Hilton Head Island is more than a photo op — it’s a workout! Climb all 114 steps to the top for a 360-degree view of the Lowcountry, then take a slow lap around the marina before the rest of the Island starts to bustle. (Harbour Town Lighthouse is open from 10 AM to sundown daily.

Afternoon: Bike, Beach, Repeat

Hilton Head is built for biking. You’ll find over 60 miles of pathways and 15,000 rental bikes for a reason. Hilton Head Island is a "Gold Level" biking community, which means it’s the safest and easiest way to soak up the scenery at your own pace. Ride beneath the live oaks, then steer toward the beach for a swim, a long walk, or a stretch of sand that feels like it was waiting for you.

Insider Tip: Many bike rental shops offer helmets. For comfort and safety, wear appropriate gear, especially if you’re riding with kids or heading out near dusk.

Evening: Sunset and Seafood

With the evening quickly approaching, return to your home away from home for some downtime before grabbing a table at one of Hilton Head Island’s over 250 restaurants. If you want to eat where the locals go for a view, try Hudson’s Seafood House on the Docks or Skull Creek Boathouse. If you’d rather stay on the sand, COAST, Oceanfront Dining in Sea Pines is a great pick.

Insider Tip: Patios abound on Hilton Head Island, so even if you choose to stay off the water for dinner, you can still experience the fresh Island air while dining at most restaurants.

Night: Stargazing and Sea Turtles

For the perfect nightcap to your first day on the Island, take a walk on the beach for a spectacular show of stars.

From May through October, Hilton Head Island keeps the lights off after 10 PM. It reduces light pollution and helps our nesting sea turtles find their way back to the ocean without getting confused.

Insider Tip: Minimizing light pollution is part of our promise to do our part in protecting Hilton Head Island’s natural habitat. You can join us in these efforts by taking the Hilton Head Island Pledge when you visit.

Day Two: Dolphins and Championship Greens

Morning: A Warm Pastry, Then the Water

Rise and shine! Start at Hilton Head Social Bakery for an authentic, warm, and flaky French croissant, then get out on the water. Book a tour with Island Time Charters for a chance to see Atlantic bottlenose dolphins, osprey, great blue herons, manta rays, bald eagles, manatees, and even sea turtles.

Insider Tip: Boat tours can book up quickly, especially during peak season, so we always recommend booking your adventure in advance.

Afternoon: Lunch, Then Choose Your Pace

After a casual lunch with Southern charm at Lowcountry Backyard Restaurant, you’ve got two excellent ways to spend the heart of your second day, depending on what “vacation mode” looks like for you.

Option A: Tee Time on a Classic Course

Hilton Head Island’s golf legacy needs little introduction. With 23 courses on the Island, there’s a hole for every golfer to take a swing at. Book a tee time at Atlantic Dunes by Davis Love III at The Sea Pines Resort or the Robert Trent Jones Course at Palmetto Dunes Oceanfront Resort. If you’d rather be a spectator, visit during the RBC Heritage presented by Boeing, every April at Harbour Town Golf Links.

Option B: Swap Golf for an Easy Outdoor Afternoon

Not golfing? Keep the afternoon light and coastal — head back to the beach for a long, unhurried stretch of sand time, or hop back on your bikes and explore a different pocket of the Island’s pathways. Hilton Head Island shines when you give it room to breathe.

Evening: A Final Southern Toast

Wrap up the 48 hours at The Porch Southern Kitchen & Bar. Located at The Beach House Resort, it’s right on the sand and features a menu rooted in sustainable, artisanal, and local ingredients. It offers a perfect serving of comfort food to wrap up your unforgettable 48 hours on America’s Favorite Island®.

Keep Planning

Want more ideas for your next visit? Request your Hilton Head Island Vacation Planner, and become a Hilton Head Island Insider to receive information on upcoming festivals and events, accommodation packages, promotions, and much more.

We can’t wait to see you soon here on Hilton Head Island.