2026 Nags Head Sailing Guide

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TRiO Restaurant & Market

Wine, beer and cheese lovers will love TRiO, an exciting retail and tasting destination in Kitty Hawk. Both a gourmet retail wine, beer and cheese shop as well as a bistro with a wine bar and tap house, TRiO offers the best of the worlds of...

Crestview Winds

SEMI-OCEANFRONT Rodanthe - Ocean Drive - You will adore the vistas from this splendid home, located just one lot back from the beach. Beach access is fast and simple, and calming on the decks is divine. Take a short walk to the Rodanthe Fishing...

  • Rodanthe
  • 5 Bedrooms
  • 4.5 Bathrooms
The Mystic Jewel

Walk into this shop and you’ll be delighted by all the glittering and sparkling from the way the mirrors and lighting show off jewelry from over 100 different designers and local artisans. Artfully-designed cases line the walls, filled with...

THE KITE SURFER

Overview Let your Outer Banks vacation take flight when you reserve The Kite Surfer for your next stay at the beach. Let your imagination set sail in this elite oceanfront retreat that is beautifully upgraded and professionally...

  • Nags Head
  • 8 Bedrooms
  • 9.5 Bathrooms
Outer Banks Blue

Since 2005, Outer Banks Blue has delivered exceptional vacations for OBX visitors. Our family-owned and locally managed rental company focuses on service and promises “a relaxing experience with a local touch.” Turn your dream vacation...

Living On The Edge CHA-02

You will be the envy of all your neighbors in this classic, truly beachfront home. This is the perfect location for the fisher in the family since it's only steps to the surf, and a short drive to the Outer Banks Fishing Pier or Oregon Inlet, which...

  • Nags Head
  • 4 Bedrooms
  • 2 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...

A Pirate's Paradise

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.A 5 Arrgh Property - WOW!  Owners’ of this property want everyone to feel at “home” when they stay here. Realizing that renters save and look...

  • Corolla
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
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...

Sand Crab 552-A

Spend your vacation at the Sand Crab! This home offers an abundance of amenities for the ideal OBX vacation! This high-quality home features beautiful hardwood flooring, great bedding and a comfortable layout. Come enjoy Sand Crab, located on the...

  • Nags Head
  • 4 Bedrooms
  • 4.5 Bathrooms
Black Pelican

Black Pelican oceanfront restaurant is one of the Outer Banks’ premier restaurants serving lunch and dinner daily. Black Pelican is where you can enjoy fresh seafood, steaks, vegetarian dishes, sandwiches and some of the barrier island’s...

Pierside Retreat 486

An unforgettable oceanfront experience awaits! Just north of the iconic Nags Head Pier, this spacious 6-bedroom, 5.5-bathroom home offers breathtaking ocean views and an unbeatable location. Pierside Retreat blends comfort and style for the perfect...

  • Nags Head
  • 6 Bedrooms
  • 5.5 Bathrooms
Old Man Charters

  Experience the Outer Banks from the water with Old Man Charters, a personalized boat tour company based in the historic fishing village of Wanchese. Departing from a private dock on the southern end of Roanoke Island, Old Man Charters...

Whalehead Retreat

Upgrades for 2025 supplied some new floor, fresh linens, the addition of a volleyball court and the garage will be converted to a theater room. Located in Corolla / 8 Bedrooms / 8 Full Bathrooms / 2 Half BathroomsThis Whalehead home is the ideal...

  • Corolla
  • 8 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.