2026 Nags Head Sailing Guide

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Events
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Donutz on a Stick

Stay, Play and Eat- Donuts, Ice Cream & Coffee Treats! Located on the Duck Boardwalk, behind Dockside Seafood, this breakfast & Dessert-Shop features treats you've never tasted before! Try the hot, made to order, donutz...

Cloud Nine

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.Cloud Nine is a semi-oceanfront retreat in the heart of Nags Head, designed to provide the ultimate Outer Banks getaway. This spacious 8-bedroom home...

  • Nags Head
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 18
Brindley Beach Vacations

Brindley Beach Vacations offers premier Real Estate and Property Management services across the entire Outer Banks. Representing more than 450 vacation rental homes, we proudly serve every region—from the southern beaches of Hatteras Island...

Pure Joy

OCEANFRONT Buxton - South Tower Circle - This cavernous and comfortable home is a PURE JOY for enormous family groups. Appreciate great vistas of the lighthouse, just a short bicycle ride away. The steps to the beach and convenient outside showers...

  • Buxton
  • 8 Bedrooms
  • 5 Bathrooms
Mike Dianna's Grill Room

Welcome to Mike Dianna's Grill Room, home to the finest seafood, USDA prime beef, amazing live entertainment and more! Come have brunch or dinner with us in Corolla on the beautiful Outer Banks. Celebrating over 20 years in the Timbuck II Shopping...

Dream Weaver

Welcome to Dream Weaver — an oceanfront escape designed for unforgettable Outer Banks memories. Located just south of Jennette’s Pier, Dream Weaver offers easy access to one of the Outer Banks’ most iconic landmarks, along with nearby dining...

  • Nags Head
  • 6 Bedrooms
  • 6 Bathrooms
Paradise Dolphin Cruises

With the best views around and the quickest access to dolphins, Paradise Dolphin Cruises is committed to offering you one of the most amazing experiences of your life! Climb aboard the Kokomo, our 34-passenger catarmaran and the area’s newest...

Calypso's Dream (North)

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.The homeowner is offering a 3% discount to past guests of Outer Banks Blue. To receive this offer, you must call our reservations team at (252...

  • Nags Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
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...

5441 - Rascoe

Always Included, complimentary linens and made beds! This "Old Nags Head" style Cottage, built in 1931, should be on an Historic Register! This antique home has been preserved with the utmost care...

  • Nags Head
  • 5 Bedrooms
  • 5.5 Bathrooms
Southern Shores Realty

Southern Shores Realty offers over 350 Outer Banks rentals from Corolla to S. Nags Head.  We've been an Outer Banks tradition since 1947, providing families just like yours with memories that last a lifetime.  Take a moment to search...

275 | Silver Dollars

6/21/26: Beach Nourishment has been completed in this area. Come and enjoy the refreshed beach! This spacious home is equipped with all the amenities necessary for an unforgettable Outer Banks Vacation! Nicely decorated and very well stocked, this...

  • Nags Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
8/22 - 8/28
$2,395  $2,995
$600 off
8/29 - 9/4
$2,195  $2,495
$300 off
Fish Heads Bar and Grill

Rustic waterfront pub at a fishing pier with a large deck for seafood eats, draft beer & live music. Fish Heads Bar and Grill is THE tiki bar of the Outer Banks. Located at Mile Post 18.5 in Nags Head, we offer a view that is second to none...

Obxscape 545

Plan an OBXscape to this magnificent home by the sea! OBXscape has a private oceanfront pool, hot tub, and kiddie pool for your enjoyment. This home is beautifully decorated with casual couches in the living room, hardwood floors in the dining area...

  • Nags Head
  • 10 Bedrooms
  • 8 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.