Beaches, Biking, and Nature: Your Weekend Itinerary to Hilton Head
Hilton Head Island offers miles of white-sand beaches, maritime forests, and well-preserved natural landscapes. Try this weekend itinerary in Hilton Head to get you started planning your vacation.
The island has a humid subtropical climate, with hot summers and mild winters. Many find that shoulder seasons like spring and fall are ideal times to visit since the temperatures are pleasant, and crowds are a little lighter. It’s an easy drive from Savannah, or you could fly in via Hilton Head Island Airport (HHH).
Hilton Head Activities and Weekend Itinerary
The natural beauty of the Hilton Head resort was the inspiration for this relaxing weekend getaway itinerary. Stress will melt away as you soak in the sand, sun, and beauty.
Friday
Arrive and unpack. A sunset beach walk helps you forget the work week and sets the tone for a weekend of relaxing while enjoying Hilton Head’s natural beauty. If you book a stay with our partner Best Nest By Beverly Serral Vacation Rentals, you will not be far from the beach. If you want to make a special trip, may we suggest a walk at Coligny Beach Park? The park is one of the most popular beach attractions on the island.
After your walk, you may enjoy a leisurely dinner at one of Hilton Head’s restaurants. If so, plan on dressing resort casual which may include sundresses, slacks, a button-down shirt. This gives you the most options if you decide to make it a spontaneous evening out.
We recommend dinner reservations, options include Cafe Al Dente in Coligny Plaza for pasta and other Italian cuisine, and The Big Bamboo if you prefer a more casual beach bar vibe. The Big Bamboo often has live music and both indoor and outdoor spaces for a relaxed night out.
If you prefer a quiet night, go home after dinner and enjoy your vacation rental’s amenities so you will be well-rested for a day of sightseeing.
Saturday
If you want to see more of Hilton Head’s natural environment, visit Sea Pines Forest Preserve for a hike or bike ride. If you need to rent a bike, reserve a rental through Sea Pines Resort Bike Rentals or Peddling Pelican Cruiser. Keep in mind that due to the natural heat and humidity, insects thrive. Be sure to wear an approved insect repellent to avoid mosquito bites.
Be sure to pre-pack snacks or a picnic lunch, pick up a few items at the Lowcountry Produce Market & Café or Farmers and Makers Market takes over The Shops at Sea Pines Center (open seasonally Spring to mid November). The Lowcountry Produce Market & Café takes pre-orders.
With 600 acres to explore, you can pick up a map at the trailhead or use an app like AllTrails for updated recommendations. Be aware that swimming isn’t allowed as it is a nature preserve and wildlife including alligators are likely to be in the water. Be sure to visit the popular The Warner W. Plahs Wildflower Field to see and possibly smell 14 varieties of wildflowers. If you have a keen eye, you might spot wildlife like white tailed deer, alligators, turtles, and over 200 species of birds.
The preserve closes at sunset, but plan on spending at least two hours, possibly longer, depending on your interests. Fishing enthusiasts also enjoy the area, if that's you, be sure to get a permit.
If all that activity makes you hungry, grab a bite to eat at Truffles Cafe. It’s conveniently close to the preserve and welcomes casual dress. Their selection of upscale salads, sandwiches, burgers, and other American-style cuisine offers something for everyone.
Sunday
What’s a trip to Hilton Head without spending time on the beach? Before heading home on Sunday, plan on a morning at the beach and a relaxing brunch.
For a casual Southern brunch, check out local favorite Palmetto Bay Sunrise Cafe at the Palmetto Bay Marina for eggs, grits, smoked salmon, or even a low carb scramble. Another option is ELA’s On the Water at Shelter Cove Harbour for classics like avocado toast, eggs benedict, and upscale seafood options.
Plan your beach visit around your brunch reservation to make the most of your last day of your Hilton Head weekend.
Where to Stay: Best Nest
Best Nest By Beverly Serral Vacation Rentals offers a collection of stylish vacation rentals with excellent service. Whether you want a comfortable cottage or a high-end villa, these rentals are near the shore and come with special amenities like pool access, full gourmet kitchens, private spas, and inviting decks or patios.
When you step inside one of Beverly’s oceanfront homes, you’ll find soaring vaulted ceilings and plenty of windows letting in natural light and delightful views. Every bedroom comes with its own ensuite bathroom, offering privacy and comfort for families or groups. When not exploring Hilton Head’s beaches and bike trails, guests can enjoy private pools and spas, grill on spacious decks, or simply relax.
