Written by Mercy B.
Mercy writes for Better Beach Rentals, highlighting all the wonderful things there are to do in Oak Island and the surrounding areas.
Oak Island is the kind of place where days move slowly in the best way, allowing you to truly rest and rejuvenate. So, how do you plan your week in such a lovely town? That’s where we come in! This 7-day itinerary is built around how we actually host friends and family when they visit. It includes a mixture of beach days, local eats, sunset views, and more. The great thing about this itinerary is that you can switch activities around or add extra beach time, whatever your heart desires. And so, without much further ado, here’s our 7-day itinerary for Oak Island.
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In This Piece:
- Days 1-7
- Book Your Oak Island Adventure Today
- Frequently Asked Questions About our Oak Island Itinerary
Day 1 – Saturday
Day 1 is when you drop off your bags at your Better Beach rental and when your vacation officially begins! Check-in at our homes is 4:00 PM, so there’s time to decompress before venturing out to find a meal. We recommend keeping dinner easy-peasy…with pizza! One of our favorite spots is Pepperoni Grill at the Beach. It’s a hand-tossed New York-style pizzeria that is the perfect choice after a long day of traveling.
Once you’ve eaten, head outside and soak in your first Oak Island sunset! One thing that makes Oak Island special is that it faces south, so you can see both sunrise and sunset from the beach. It’s a magical way to end the day.
Day 2 – Sunday
Sunday is your first full beach day! Bring a cooler filled with refreshing beverages and kick back into a beach chair with your shades on. When hunger strikes, you can pack a lunch that you’ve made in one of our fully equipped kitchens. You can also grab a sandwich from the Oak Island Sub Shop, a local favorite that is sure to be a hit with your whole crew.
In the afternoon, make a sweet stop at OKI Scoops and Donuts for ice cream or a treat to cool off. For dinner, head to Shagger Jacks, where you’ll find an inviting pet-friendly patio and something for everyone on the menu. From fried oysters to peel-and-eat shrimp, you can satisfy all your seafood cravings here!
Day 3 – Monday
Start the day with coffee and breakfast at Ruby’s Coffeehouse, a local staple that’s worth the stop. After breakfast, head back to the beach for some shell hunting! Oak Island is perfect for some easy-breezy beachcombing.
For lunch, pick up fish tacos or a Long Beach burrito from Kai-Joe's. Once you’ve polished those off, spend the afternoon at Oak Island Jungle Golf or the Golf Barn. These provide fun golfing activities for all skill levels and are a great way to spend an hour or two.
In the evening, take a short drive into Southport for dinner at Mr. P’s Bistro. It’s an upscale but welcoming spot that specializes in low-country cuisine and seafood. If you’ve ever wanted to try shrimp and grits or okra gumbo, now’s your chance!
Day 4 – Tuesday
Tuesday is for exploring nearby Southport, one of North Carolina's most charming coastal towns! Start with brunch at Café Koa, some sweet treats from Little Bitty Donuts, or grab coffee and a sandwich from Southport Coffee Co. before strolling through town.
Spend the morning browsing shops like Bullfrog Corner, visiting the famous Christmas House, and exploring local antique stores. Then you can wander the streets lined with historic Victorian homes and take photos!
In the afternoon, grab an iced latte and a snack from Port City Java. Then make a stop at the Fort Johnston–Southport Museum & Visitors Center, where you can check out numerous exhibits that highlight the movies and TV shows filmed here. It’s cool to see how often Southport appears onscreen!
For dinner, hit up Provision Company, one of the best spots for fresh coastal seafood. Afterwards, enjoy a drink with a view of the water at American Fish Co. or The Mullet Bar. Just remember if you’re drinking, drive responsibly or have a designated driver!
Alternatively, you can also book a sunset boat cruise with Captain Andy Water Tours. Sunset is one of the best times to spot dolphins! You can also wrap up the night with the Old South Ghost Tour, which shares fascinating and spooky stories from Southport’s past.
Day 5 – Wednesday
Another beach day is always a good idea! Start with coffee or breakfast from Island Jo, then spend the morning enjoying the sun, sand, and surf.
In the afternoon, it’s time to go fishing. You can do this from shore or a pier, or by hiring a local fishing charter for a guided experience. If fishing isn’t your thing, this would also be the perfect moment for kayaking, biking, or just relaxing back at your Better Beach vacation rental.
Another fun option is to head over to Throw Baxe Axe House, an axe-throwing house and board game lounge that provides fun for the whole family! This is also an excellent after-dinner option, too.
Speaking of dinner, head back into Southport and eat at Fizzy Jane’s, which is known for its ambiance and creative comfort food. Order up delectable fare such as roasted carrots with honey ricotta and crab-stuffed mahi. You can then end your lovely day with a movie night at Surf Cinema and experience a little Hollywood magic.
Day 6 – Thursday
Start Thursday with a visit to the picturesque Oak Island Lighthouse and get a tour to the top. It’s important to note that these tours must be booked in advance and are offered only on Tuesdays, Thursdays, and Sundays from May 1 through September.
Spend the rest of the day at the beach or relaxing before dinner at Koko Cabana on the Oak Island Pier. Sunset here is hard to beat. Crowd favorites include the poke bowl, tuna nachos, and firecracker shrimp. Plus, don’t forget to try one of their creative cocktails! It’s a truly lovely way to spend your evening.
Day 7 – Friday
For your final full day, start with breakfast at Old Bridge Diner, named Best Diner in North Carolina by Yelp in 2023. Then squeeze in one last beach day, because, after all, that’s probably the main reason why you’re here, isn’t it? If you happen to see the Sunset Slush cart roll by, make sure to get an Italian ice!
In the evening, get dressed up for a goodbye dinner at Edgewater 122, where you’ll enjoy a seasonal menu and views overlooking the Cape Fear River and the Intracoastal Waterway. What a lovely way to end your trip!
Checkout Day – Saturday
On your way out of town, make one last stop at Island Jo’s for coffee and breakfast. It’s the perfect way to end an amazing trip to Oak Island.
Book Your Oak Island Adventure Today
Featured Rental: Cordoba
Ready for your Oak Island vacation? Yes, you are! Well, almost—the first, and most important step is to find a vacation rental that you like. Here at Better Beach Rentals, we’re happy to assist. Our homes offer loads of amenities that are sure to make your stay even better. From homes with private pools, pet-friendly abodes, to oceanfront rentals, we’ve got it all. So, choose your fave and book it. We look forward to your visit!
Frequently Asked Questions About Our 7-Day Oak Island Itinerary
Is this 7‑day Oak Island itinerary good for families?
Yes! This itinerary is very family‑friendly. It includes beach time, kid-friendly dining spots, mini golf, ice cream stops, and movie nights.
Do I need to follow this Oak Island itinerary exactly?
Nope! This itinerary is flexible. Feel free to mix and match days, add more beach time, or skip anything that doesn’t fit your vibe.