Have you been dreaming of days spent relaxing on the beach? Have you imagined yourself kayaking through the winding marsh seagrass? Does the sound of exploring historical sites make you tick? If so, then it's time to plan a vacation to Hilton Head!
Below, we’ve outlined seven action-packed days that will help you make the most of your time. Whether your ideal vacation includes lazy days filled with brunching and long bike rides near the beach or a resort-style getaway with golf, tennis, and wine tasting, you’ll find it all when you book your stay with Beach Properties on Hilton Head.
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How to Spend 7 Days in Hilton Head
Day 1
Breakfast (or Brunch) of Champions
Start your day off on the right foot with a delicious breakfast or brunch! Some of our favorite restaurants for brunch and breakfast include:
Palmetto Bay Sunrise Cafe – Enjoy breakfast all day at this popular restaurant. Dine inside or sit on the dog-friendly patio and soak in the incredible island weather. Popular dishes include biscuits and gravy, crab cake benedict, and fluffy French toast.
- Open: Wednesday – Sunday 6 AM to 2 PM | Closed Monday and Tuesday
- Google: 4.7 ⭐️
- Price: $-$$
The Skull Creek Boathouse – Gorgeous waterfront views and award-winning food await at this landmark Hilton Head restaurant. Great for the whole family (even your furry friends). Be sure to try the Sunday brunch sushi and ceviche, or go all out with the Boathouse Sampler: a smattering of some of the most popular menu items like dill pickle chips, shrimp, calamari, and more.
- Open: Monday – Thursday 11 AM to 9 PM | Friday & Saturday 11 AM to 10 PM | Sunday 10 AM to 9 PM
- Google: 4.5 ⭐️
- Price: $$
Harold's Diner – Craving a hearty start to the day? Harold’s Diner is your go-to for all the classic breakfast staples from sizzling bacon and eggs to fresh coffee, pancakes, and waffles. Keep in mind, they’re cash-only, so be sure to come prepared.
- Open: Monday – Friday 7:30 AM – 3 PM (Breakfast and Lunch) | Saturday 7:30 AM – Noon (Breakfast Only)
- Google: 4.5 ⭐️
- Price: $
Watusi Cafe – Looking for a spot with vegetarian, vegan, and gluten-free offerings alongside traditional breakfast favorites? Watusi Café has you covered. This family-owned restaurant serves breakfast and lunch, as well as desserts and a selection of fun cocktails and wine.
- Open: Monday – Sunday 7:00 AM – 2:30 PM
- Google: 4.5
- Price: $ - $$
Beach Bums
Relax on the beautiful beaches of Hilton Head Island! Take in the smell of the salty air. Feel the sun on your back. Dip your toes in the water. The beach is what draws visitors to the island. The rest is what makes them want to stay even longer!
Day2
Eat Local: Farmers Markets
Grab some fresh, local produce from a farmers’ market! You’ll also find a wide variety of sweet treats, delicious eats, and Lowcountry ingredients!
- Village at Wexford Farmers Market — Wednesday from 10 AM to 2 PM
- The Farmer’s Market at Sea Pines Center — Tuesday from 10 AM to 2 PM
- Farmers Market at the Coastal Discovery Museum — Tuesday from 9 AM to 1 PM
- Bluffton Farmers Market — Thursday, September through May, from 12 PM to 4 PM | June – August from 10 AM to 2 PM
It’s Time for an Adventure
Whether you’re interested in trying out a new watersport or hoping to stretch your legs on a long hike, you’re in luck. Hilton Head Island is home to an exciting array of outdoor adventures!
Day 3
Tours: Explore the Island
Tours are one of the most efficient and fun ways to get to know the island! You can book a kayak tour to float through the marsh, a boat tour for scenic rides or fishing, or dolphin tours to get up close to some of the most popular marine life.
Order Delivery for Dinner
If you’re not feeling up to dining out, order in instead! Try one of these amazing delivery options for your lazy night back at the vacation rental.
- Restaurant Express – Ribs, lobster, steak, and more
- Local Pie Wood-Fired Pizza – Garlic knots, fried mozzarella, and crispy crust classic pizza pies
- Nunzio – Perfect blend of Italian classics and Lowcountry favorites. Place delivery orders via chownow.
Day 4
Retail Therapy
Find the perfect souvenir to commemorate your trip or that one-of-a-kind piece at a local antique store. Regardless of what you’re in search of, the local shops on Hilton Head Island have you covered.
- Coligny Plaza – 25 shops and 24 restaurants are waiting when you’re looking for that just right thing.
- Shelter Cove Marina – You’ll find shops, spas, and dining hot spots, all situated along a scenic waterfront marina at this popular retail location.
- Tanger Outlets – From luxury brands to national retailers, you’ll find all sorts of items at Tanger Outlets.
Day 5
Sightseeing and Historical Landmarks
When you take your time to explore the history of the South Carolina Lowcountry, you’ll gain a new appreciation for Hilton Head. Enhance your vacation with a trip down the Gullah Heritage Trail and wander beneath the ancient oak trees of Daufuskie Island. Stop by a local deli for a leisurely lunch afterward!
- Historic Mitchelville Freedom Park - Learn about the first self-governed community of formerly enslaved people in the United States at this historic landmark.
- Coastal Discovery Museum - Explore Hilton Head’s natural and cultural history through hands-on exhibits, boardwalks over the marsh, and beautifully preserved historic buildings.
- The Sandbox Children’s Museum - A bright, engaging space where kids can climb, build, imagine, and explore through hands-on exhibits designed just for them. They have a limited capacity, so it’s best to reserve your spot ahead of time to guarantee entry.
- Gullah Heritage Trail Tours - A guided experience that shares the stories, traditions, and lasting influence of the Gullah people on Hilton Head Island. Through narrated stops and firsthand insight, you’ll gain a deeper understanding of the island’s culture and the community that shaped it.
- Stoney-Baynard Ruins - Walk through the remains of an early 19th-century plantation home tucked among the live oaks in Sea Pines. The site offers a quiet look at Hilton Head’s layered past, with interpretive signs that help bring the history of the land and the people who lived there into focus.
After learning all about the heritage and history of the Lowcountry, why not celebrate the great culinary contributions of the region with a spectacular dinner? If it’s seafood you’re looking for, you can’t go wrong with these suggestions:
Reilley’s Grill and Bar – Elevated pub fare including steaks, fresh seafood, and more. Try the iron skillet mussels, the espresso-rubbed ribeye, or something cozy like the meatloaf sandwich.
- Open: Monday – Saturday 11:30 AM to 10 PM | Sunday 11 AM to 10 PM
- Google: 4.4 ⭐️
- Price: $$
Coast Oceanfront Dining – Ocean views and Caribbean-inspired dishes await at this popular Sea Pines restaurant. Indulge in raw bar selections, succulent crab legs, savory soups, fresh salads, and delicious fresh-catch specialties.
- Open: Daily for lunch from 11:30 AM to 4 PM and dinner from 4 PM to 9 PM
- Google: 4.5 ⭐️
- Price: $$-$$$
Hudson’s Seafood House on the Docks – Every seat offers incredible views of the water, whether you’re seated inside or out on the patio. Pair the atmosphere with delectable bites of fried green tomatoes, oysters Rockefeller, or little neck clams for a true coastal feast you won’t forget.
- Open: Monday – Saturday 11 AM to 9:30 PM | Sunday 10 AM to 9:30 PM
- Google: 4.6 ⭐️
- Price: $$$
Fishcamp on Broad Creek – Steeped in tradition as old as Hilton Head Island itself, Fishcamp prides itself on offering unbeatable service and second-to-none food. Visit them for PEI mussels, fried Maine lobster tail, fresh shrimp cocktail, stuffed flounder, and a variety of coastal fish favorites.
- Open: Daily 11 AM to 10 PM
- Google: 4.5 ⭐️
- Price: $-$$
Day 6
Wineries, Breweries, and Nightlife Fun
With one last full day on Hilton Head, why not spend the morning back on the beach, soaking up the salt air and sunshine, before heading back to your vacation rental for a light lunch? After showering off the sunscreen, it’s time to get dressed up for a night on the town. With wineries, jazz bars, breweries, and more to explore, there’s a perfect vibe no matter what mood strikes your fancy.
- Island Winery – Wine tastings featuring six wines for $10. Bring your own snacks and enjoy a glass of their select favorites.
- Hilton Head Brewery – With 16 beers on tap, all brewed on-site, you’re sure to find one you love. We recommend the Muddy Creek Porter for the dark beer drinkers or the Coastal Cream Ale for something lighter that’s still cleverly unique.
- Jazz Corner – Their extensive menu pairs perfectly with a night of smooth jazz. Check out the schedule and be sure to book your tickets in advance.
- The Rooftop Bar – Dueling piano shows, concert series, and great cocktails—all the makings of a perfect night out on the town. Don’t miss out on their excellent happy hour offerings from 4 PM to 7 PM.
Day 7
Brunch Before Hitting the Road
Enjoy a slow wake-up with coffee on your balcony before loading up and bidding farewell to your beach home away from home. On your way out of town, stop for brunch at any of the great restaurants we’ve mentioned that you didn’t get a chance to try yet, and maybe take one last walk along the shore before heading home. While you’re indulging in your final Hilton Head meal, you can start dreaming up your next visit!
Fun Facts, Local Tips, & Insider Info
Did You Know?
- May through October is loggerhead turtle nesting season on Hilton Head. During this time, baby turtles use the moonlight to navigate their way to the ocean. Houses and buildings visible from the beach must turn off their lights and close their curtains at night.
- Bottlenose dolphins are frequently seen on Hilton Head. These creatures are extremely intelligent, friendly, and social. One may approach your boat to say, “Hi!” Please remember that feeding the dolphins is illegal.
- Hilton Head Island is home to over 12 miles of sandy beaches and 108 miles of paved bike paths! It is a paradise for outdoor enthusiasts.
How to Enjoy Peak Season Like the Locals
- Family concerts take place each night in the summer. You’ll find performances by local artists like Gregg Russell and Shannon Tanner at places like Shelter Cove Harbour and under the Liberty Oak in Sea Pines, as well as other concerts.
- Every Tuesday from Memorial Day to Labor Day Weekend, fireworks shows take place at Shelter Cove Marina as part of Harbourfest. You can look forward to live music, family-friendly activities, local vendor booths, and more.
Unique Activities
- Yoga on the beach is a fun way to stay active during your vacation. Classes are available each Saturday and Sunday morning near Coligny Plaza Beach Park.
- If you and the kids would like to learn more about golf, check out the International Junior Golf Academy Summer Golf Camps.
- For a customized Lowcountry adventure, try out Outside Hilton Head. You choose from a number of experiences that will show you a different side of Hilton Head Island and the surrounding areas.
Stay in a Private, Luxury Vacation Rental
Visiting Hilton Head Island is all about making the most of your stay! Our 7-day itinerary is your personal guide to enjoying all the top activities and restaurants in the area. Now that your trip is planned, be sure to browse our accommodations! Our luxury vacation house and villa rentals in the Sea Pines Resort, Forest Beach neighborhood, and Sea Crest Resort offer unmatched relaxation and unique features. What are you waiting for? Book your escape today!
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