2026 Nags Head Sailing Tours Guide

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Wanchese Marina

Wanchese Marina offer one of the finest fleets of professional charter fishermen, charter booking service, dolphin tours, dive charters, shrimp charters and even crabbing charters. We have both diesel and non-ethanol fuel, a professional fish...

4740 - August's Summer Place

Always Included, complimentary linens and made beds! August's Summer Place has everything you need and more for a memorable Outer Banks vacation! Located in Kitty Hawk, August's Summer Place is near...

  • Kitty Hawk
  • 4 Bedrooms
  • 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...

SUNNY DAYZ

Overview As soon as you arrive at Sunny Dayz, you'll experience the relaxing shift towards vacation-mode. Outfitted with ten spacious bedrooms, this oceanfront estate offers ample space for large groups or family reunions, and the long...

  • Corolla
  • 10 Bedrooms
  • 10 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...

261 | The Beach House

This Nags Head Oceanfront home boasts outstanding Ocean Views & a spacious floor plan that includes 2 Oceanfront Private Suites, Hardwood Floors, Rec. Room w/Pool Table, Private 12x26 Swimming Pool, custom décor, & special touches...

  • Nags Head
  • 7 Bedrooms
  • 5.5 Bathrooms
  • Sleeps 16
5/16 - 5/22
$3,495  $3,995
$500 off
5/23 - 5/29
$4,995  $5,895
$900 off
5/30 - 6/5
$6,395  $7,495
$1,100 off
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...

Seaside NAN-05

Seaside is a comfortable cottage that is just 75 feet from the beautiful beaches of South Nags Head at milepost 19.5!An impressive vaulted ceiling accents the kitchen and dining spaces which flows into the living room. Spend mornings sipping coffee...

  • Nags Head
  • 4 Bedrooms
  • 2 Bathrooms
Jimmy's Seafood Buffet

Home of the Crab Leg & Lobster Buffet for 26! years! Jimmy’s Seafood Buffet is a great stop for an all you can eat affordable dinner extravaganza. The buffet offers over 100 different items. It even serves Jumbo Alaskan crab legs and Jumbo...

LA RESIDENCIA

Overview Step into La Residencia, an oceanfront villa with breathtaking ocean-to-sound vistas located in the premier community of Pine Island in Corolla. From the moment you enter this vacation home, guests are treated to a beautifully...

  • Corolla
  • 9 Bedrooms
  • 11.5 Bathrooms
Fishing Unlimited Boating Center

Owned by Garry Oliver, the proprietor of the Outer Banks Fishing Pier, this small wooden aqua blue-colored store on the Nags Head-Manteo causeway has been serving the needs of fishermen for decades. A full line of tackle is available for all types...

Duckaway 177

It would be hard to find a better location in the Village of Duck than DuckAway. This home is located between the beach and the village, with a short walk to the beach on one side and a short walk to the center of town on the other side. It is the...

  • Duck
  • 5 Bedrooms
  • 4 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...

PIRATES ESCAPE

Overview Pirates Escape is a beachfront retreat located in Nags Head. This home is professionally decorated and offers guests popular amenities and unique finishes. Interior features include eight inviting suites, an elevator, an open...

  • Nags Head
  • 8 Bedrooms
  • 10 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.