2026 Nags Head Sailing Guide

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Events
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Coastal Smoothie Cafe

At Coastal Smoothie Cafe, we have created a menu and atmosphere that is designed to be as unique as the northern shores of the Outer Banks. Our creations utilize fresh local produce when possible. There is nothing better than local NC strawberries...

Shaka Shack SWB-3

Looking for an unforgettable four-wheel drive area home with panoramic views and amenities that will make you never want to leave? Well, Shaka Shack is the place for you! This home has everything for the perfect vacation! Nestled only a short drive...

  • Carova
  • 6 Bedrooms
  • 4.5 Bathrooms
American Pie

Discover the best homemade ice cream and authentic made-from-scratch New York Style pizza the Outer Banks has to offer at American Pie in Kill Devil Hills. An Outer Banks favorite for lunch, dinner or a delicious scoop of scrumptious ice cream after...

BLUE HEAVEN

Overview To experience a slice of waterfront paradise, reserve Blue Heaven, a beach retreat located on the Currituck Sound. Situated a short walk to the beach and an easy bike ride to Duck Village, this popular vacation home's superb...

  • Duck
  • 5 Bedrooms
  • 5 Bathrooms
Kitty Hawk Kites

Kitty Hawk Kites has been Teaching the World to Fly since 1974 and is home to the world’s largest hang gliding school. As the Outer Banks leader in quality outdoor recreation and adventure, Kitty Hawk Kites offers more than 30 activities to...

WHITECAPS

Overview Located on the oceanfront in Nags Head, Whitecaps offers 3,100 square feet of living space, seven bedrooms, a fully-fenced private pool, hot tub, rec room, and more! Undoubtedly, you and your vacation group will enjoy your...

  • Nags Head
  • 7 Bedrooms
  • 6 Bathrooms
Cosmo's Pizzeria Southern Shores

If you're searching for great pizza on the Outer Banks, look no further than Cosmo's Pizzeria at The Marketplace in Southern Shores! We offer authentic New York-style pizza made fresh and just the way you like, using only the highest quality...

Serendipity

Serendipity is the perfect home for all seasons. Enjoy your days gazing at the spectacular ocean view and soaking up the rays from the top deck crow’s nest. After a long day at the beach, it's just a few steps to the cottage for an evening of...

  • Kill Devil Hills
  • 3 Bedrooms
  • 2 Bathrooms
Flip Flop Shops

Free Your Toes!®Live, work and play with your toes exposed® and the freedom of flip flops on your feet. 



Mr. Sandman

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.You'll sleep soundly at Mr. Sandman in Corolla! Located in the Whalehead Beach community, this house is perfect for multi-family groups, with multiple...

  • Corolla
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
Gray's

Gray’s Outer Banks Lifestyle Clothing Company offers the absolute best in Outer Banks T-shirts and Sweatshirts including Champion, Under Armour with "Outer Banks” and Gear! We carry quality fashions and accessories for the whole family...

MY SUNSHINE

Overview Wake up to unimaginable sunrises when you reserve My Sunshine, a smartly designed home with generous oceanfront windows to capture breathtaking coastal panoramas. This popular vacation retreat has guests returning year after...

  • Nags Head
  • 5 Bedrooms
  • 5.5 Bathrooms
Duck Town Park & Boardwalk

Duck Town Park provides a playground for all seasons and more. Its 11 acres consist of a mix of Maritime Forest, willow swamp, open lawn with amphitheatre and picnic shelters, all sitting next to the lovely shallow waters of scenic Currituck Sound...

Coastin' KIN-58

This is your personal paradise on gorgeous Hatteras Island! Stunning sound views are yours from the large decks of Coastin', formerly known as Fish Tales. After a long day at the beach, relax with family and friends as you experience a breathtaking...

  • Avon
  • 6 Bedrooms
  • 7.5 Bathrooms
5/30 - 6/6
$3,927  $4,410
$483 off
6/6 - 6/13
$4,126  $4,658
$532 off
8/22 - 8/29
$4,724  $5,256
$532 off
Kitty Hawk Kites

Kitty Hawk Kites has been Teaching the World to Fly since 1974 and is home to the world’s largest hang gliding school. As the Outer Banks leader in quality outdoor recreation and adventure, Kitty Hawk Kites offers more than 30 activities to choose from, so get out that pen and start crossing things off your OBX bucket list today! Visit KittyHawk.com or call 1.877.FLY.THIS to book your Kitty Hawk Kites adventure today.