2026 Nags Head Sailing Guide

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Events
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Back Country Safari Tours

Discover wild Spanish Mustangs and our unique Barrier Island ecology on the Wild Horse Safari. Explore over 30 miles of "off road" beach, dune and sand trail and ride with a professional naturalist guide in a custom 4x4 open-air Safari Cruiser, or...

Dune Castle KSD-14

You will feel like royalty at Dune Castle! This spacious, comfortable Oceanside home will keep everyone in the family entertained. You will love the convenience of the grocery lift that can send both your luggage and the groceries upstairs. There...

  • Avon
  • 4 Bedrooms
  • 5.5 Bathrooms
Captain Johnny's Dolphin Tours

Join Captain Stuart Wescott aboard The Captain Johnny boat for a Guaranteed Dolphin Watch cruise in protected waters off the Outer Banks, NC. This two hour cruise is ideal for all ages. Enjoy breathtaking views as you listen to a...

A SENSE OF PORPOISE

Major Renovations for 2026 include: brand new kitchen, remodeled baths and new LVP flooring in main living areas! Discover your ultimate Outer Banks escape at “A Sense of Porpoise,” a beautifully appointed oceanfront retreat tucked away in the...

  • Southern Shores
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Sleeps 8
11/28 - 12/5
$2,583  $2,924
$341 off
12/5 - 12/12
$2,394  $2,924
$530 off
12/12 - 12/19
$2,489  $2,924
$435 off
1/2 - 1/9
$2,249  $2,598
$349 off
1/9 - 1/16
$2,332  $2,598
$266 off
1/16 - 1/23
$2,366  $2,598
$232 off
1/23 - 1/30
$2,366  $2,598
$232 off
1/30 - 2/6
$2,366  $2,598
$232 off
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...

EDGEWATER

Panoramic ocean view up and down. Excellent off-season retreat. Remodeled spa bathroom, new beach steps, walkway, dune deck. Renovated decks.Level 1:4 bedrooms (2 with Queens, 2 with Twins), 2 baths (1 with ocean view, jacuzzi tub and separate steam...

  • Southern Shores
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
11/29 - 12/6
$2,072  $2,412
$340 off
12/6 - 12/13
$1,991  $2,412
$421 off
12/13 - 12/20
$2,153  $2,412
$259 off
OBX Shipping Center

We are the only Authorized Shipping Center on the OBX for FedEx, UPS and DHL. Come to OBX Shipping Center for all your shipping and office needs. We offer Notary services, copies, faxing, laminating, among other office services. You do the...

K7002 Flip Flop

Welcome to Flip Flop by KEES Vacations! Located in the heart of Kill Devil Hills and perfectly situated near Avalon Fishing Pier, Flip Flop allows for easy vacationing. As a semi-oceanfront property, this six-bedroom home boasts ocean views from the...

  • Kill Devil Hills
  • 5 Bedrooms
  • 6 Bathrooms
Miss Oregon Inlet

Oregon Inlet Fishing Center is the home of the largest and most modern charter boat fishing fleet on the eastern seaboard. A full service marina in Nags Head NC, Oregon Inlet offers a comprehensive charter boat fishing experience for the "old salt...

Knot for Sail

Step into Knot for Sail, a soundfront home that perfectly blends coastal elegance with unparalleled comfort. The spacious living room is bathed in natural light from expansive windows and offers sweeping views and plush seating around a modern...

  • Duck
  • 5 Bedrooms
  • 4.5 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...

CAROLINA

Situated on the highest sand dune in Southern Shores in a quiet neighborhood with a pickleball court, playground, basketball and tennis courts all within a short walking distance, bright, spacious and airy home.  In addition to the great room on...

  • Southern Shores
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Sleeps 8
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...

Moments Of Grace

Located in Corolla / 4 Bedrooms / 3 Full Bathrooms / 1 Half BathroomAwaken with the sunrise in this elegantly decorated Villa with ocean vistas. Entertain and relax in the roomy living area with wood floors, breakfast bar, and central sound...

  • Corolla
  • 4 Bedrooms
  • 3 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.