Your Perfect 3 Days on Hilton Head Island Itinerary

Have you been hoarding your PTO days? Then it’s time for a vacation. Hit the road and escape to a beautiful, warm, and sunny destination. We have everything you need to spend an unforgettable 3 days on Hilton Head Island. Read on to discover the best restaurants, attractions, and outdoor adventures so that you can make the most of your time here. Then, be sure to subscribe to our blog to stay in the know! 

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How to Spend 3 Days on Hilton Head Island 

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: 

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! 

Day 2 

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! 

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! 

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.


Planning to Stay Longer? Get Your Free Copy of Our 7-Day Itinerary

toutOur free 7-day itinerary covers everything you need to know about planning the ultimate getaway to Hilton Head Island. Inside, you will find the best local suggestions for things to do, such as: 

  • Where to get groceries and how to have them delivered
  • The best places to get food delivery 
  • Where to see the best sunsets
  • How to plan the perfect beach day
  • Where to find the best local eats
  • The best golf courses 
  • Our favorite water sports and activities
  • Rainy day alternatives
  • & more

Get Your 7-Day Itinerary


Stay in a Private, Luxury Vacation Rental 

5 Jessamine Place pool exterior viewNow that you know how to make the most of your 3 days on Hilton Head Island, it’s time to decide where you’d like to stay. Our luxury vacation house and villa rentals in the Sea Pines Resort, Forest Beach neighborhood, and Sea Crest Resort set the scene for the ultimate getaway. Each of our properties has something unique to offer. Browse our selection and choose the perfect rental for you!

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