2026 Nags Head Sailing Guide

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Awful Arthur's Oyster Bar

Welcome to the home of the happy oyster where for over 40 years the oyster has been our world. The Outer Banks only authentic oyster bar is the place to enjoy sensational fare from the sea washed down with your favorite brew or cocktail. We serve by...

5425 - The Sandfiddler

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! NEW FOR 2026: All new decks and beach walkway. If you're looking for a beautiful house with incredible ocean views...

  • Nags Head
  • 6 Bedrooms
  • 6.5 Bathrooms
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...

SALTY SURFER

Experience bright sunshine and serene oceanside living at Salty Surfer, a Carolina Designs oceanfront home in the Village at Nags Head, situated directly behind the dunes with the Atlantic just steps away. With the smell of sweet salt air and...

  • Nags Head
  • 6 Bedrooms
  • 4.5 Bathrooms
Henry's Restaurant

Henry's Restaurant offers down home, simple food done Outer Banks style. Henry's Restaurant has been serving the Outer Banks of North Carolina since the summer of 1989. They are pleased to be considered one of the most popular restaurants in Dare...

Ocean Oasis W-05

Welcome to your very own Ocean Oasis! Nestled in front of a pond in the midst of nature, this amazing brand-new construction, is sure to become a family favorite. Enjoy watching the wildlife that sometimes visits while having that first cup of...

  • Waves
  • 7 Bedrooms
  • 6.5 Bathrooms
Big Buck's Homemade Ice Cream

Serving our customers on the Outer Banks since 1994, Big Buck's ice Cream is dedicated serving you “The Best.” We offer a full line of super-premium ice cream products, smoothies, chocolates, and custom-made ice cream cakes! 2 locations...

LADY CORTEZ

“Lady Cortez” is located in Duck’s Carolina Dunes Oceanside community and is an easy walk to the ocean and private sound access as well as the walking and bike path that leads to the quaint Village of Duck, NC. This spacious, bright and well...

  • Duck
  • 6 Bedrooms
  • 5.5 Bathrooms
  • Sleeps 14
8/22 - 8/29
$2,935  $3,713
$778 off
8/29 - 9/5
$2,573  $3,206
$633 off
9/26 - 10/3
$2,246  $2,681
$435 off
10/3 - 10/10
$2,339  $2,681
$342 off
10/10 - 10/17
$2,354  $2,681
$327 off
10/17 - 10/24
$1,991  $2,210
$219 off
10/24 - 10/31
$2,005  $2,210
$205 off
Flip Flop Shops

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



Beach Bunker 268

Everyone needs a Beach Bunker, and this charming retreat is the perfect place to start! Thoughtfully furnished for comfort and relaxation, this inviting home offers a laid-back setting where your family can unwind after sun-filled days on the Outer...

  • Kitty Hawk
  • 4 Bedrooms
  • 3.5 Bathrooms
Pigman's Bar-B-Que

You haven’t experienced North Carolina until you’ve experienced North Carolina BBQ, and Pigman’s Bar-B-Que offers excellent North Carolina BBQ meals served with southern hospitality. Pigman’s offers traditional eastern...

1776 - Changes in Attitudes

Always Included, complimentary linens and made beds! You'll be sure to have a change in attitude at this Corolla vacation rental! Changes in Attitudes is located on the oceanside of Corolla near...

  • Corolla
  • 6 Bedrooms
  • 6.5 Bathrooms
Sun Realty

Sun Realty offers the Best Selection of Vacation Rentals on the Outer Banks. Our large selection of Outer Banks rentals means you can choose from a wide range of amenities, including private swimming pools, hot tubs, theater rooms, game rooms, pet...

SIR WALTER RALEIGH

A private home theater sits behind accordion curtains at Sir Walter Raleigh, a Carolina Designs oceanfront estate at Milepost 10.5 in Nags Head, where those curtains slide open to a rec room with a pool table, shuffleboard, foosball, and...

  • Nags Head
  • 8 Bedrooms
  • 9 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 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.