2026 Nags Head Sailing Guide

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Events
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Brew Thru

No trip to the Outer Banks is complete without cruising through Brew Thru, the Outer Banks’ original drive thru convenience store. Whether you’re looking for a refreshing cold beverage of Coke, Pepsi and other soft drinks on the go...

TRADE WINDS

Just five lots back from the ocean in Corolla's Pine Island community, TRADE WINDS pairs a 30-foot private pool with a perk few Outer Banks homes offer: discounted golf fees. Carolina Designs welcomes you to this five-bedroom Pine Island...

  • Corolla
  • 5 Bedrooms
  • 4.5 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...

5377 - Memorial Blvd.

Always Included, complimentary linens and made beds! Partials available in the off season, must call to book. This Kill Devil Hills home is perfect for your next Outer Banks vacation! Located on...

  • Kill Devil Hills
  • 4 Bedrooms
  • 4 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...

718 | Spirit Of Kitty Hawk

The "Spirit Of Kitty Hawk" has added a luggage lift for the 2026 season. The top and mid-level private suites now have tiled walk-in showers (bath tubs removed), and the parking area has been expanded. Your family is sure to enjoy the great Ocean...

  • Kitty Hawk
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Sound Feet Shoes

Sound Feet Shoes is family owned and operated. Sound Feet has been in the retail shoe business for over 72 years, opening their first store in 1953. They provide the best customer service and are the only Outer Banks’ area full service shoe...

GRANDE ATLANTIS

Tucked behind a private dune deck at Milepost 7.5, Grande Atlantis hides something few Outer Banks homes can claim: a poolside cabana bar with bar-height seating, a mini-fridge, and a seasonal outdoor TV. This 10-bedroom oceanfront Carolina...

  • Kill Devil Hills
  • 10 Bedrooms
  • 10.5 Bathrooms
Jolly Roger

When you first catch sight of The Jolly Roger, you might be unsure exactly what to think of it. Since its conversion from a gas station/grocery store to a restaurant in 1972, The Jolly Roger has been anything but your ordinary Outer Banks...

K7309 Tidewater Tranquility 4 Bedroom Ho...

Welcome to Tidewater Tranquility at The Tides Oceanfront Community by KEES Vacations! Beach Set Up Service, Village Beach Club, and Westside Athletic Club included with your stay! At The Tides, you can indulge in a unique vacation experience like no...

  • Kill Devil Hills
  • 4 Bedrooms
  • 5 Bathrooms
Poke Box

PokeBox offers fresh, quick, simple, healthy poke bowls in Nags Head. Choose your items and build your bowl. Tuna, salmon, chicken, steak, shrimp and tofu options available. Mix in your favorite veggies, sauces and toppings for the perfect poke...

Dot's Dream 436-A

Dot's Dream in Nags Head is a spacious, six-bedroom, semi-oceanfront home featuring a private pool, hot tub, and game room. With beach access practically across the street, ocean views to the east, and Jockey’s Ridge National Park to the west...

  • Nags Head
  • 6 Bedrooms
  • 5.5 Bathrooms
Miller's Waterfront Restaurant

MILLER’S OFFERS ONE OF THE FEW TRULY WATERFRONT DINING EXPERIENCES ON THE OUTER BANKS. Enjoy casual dining in our downstairs family-friendly seafood restaurant, or our signature drinks and grill menu in our upstairs deck bar while watching...

WHISPERING WAVES

“Whispering Waves ” is an escape to coastal bliss located in the charming town of Duck, North Carolina. This spacious 5-Bedroom Home with Private Pool and Easy Beach Access is your perfect vacation getaway! It offers the ideal blend of comfort...

  • Duck
  • 5 Bedrooms
  • 5.5 Bathrooms
  • Sleeps 10
11/8 - 11/15
$1,813  $2,187
$374 off
11/15 - 11/22
$1,947  $2,187
$240 off
11/29 - 12/6
$1,880  $2,187
$307 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.