2026 Nags Head Sailing Tours Guide

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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...

Why Knot

OCEANFRONT Avon — Ocean View Dr. — New for 2026! — When it comes to booking the ideal Hatteras Island hideaway, the question shouldn’t be why, but WHY KNOT? This six-bedroom/four-bath home has all the answers encompassed within cavernous...

  • Avon
  • 6 Bedrooms
  • 4 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...

Skipper's Landing

SOUNDSIDE Avon — Kinnakeet Shores Are you looking for a beach home on the lake in Kinnakeet Shores with pretty water vistas, space for the family, a fast 5-min. walk to the beach and walking distance to the grocery store, shopping and eateries...

  • Avon
  • 5 Bedrooms
  • 4.5 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...

High Dune

OCEANFRONT Avon - Fitzwater Ct. - Everything one could want for the ideal vacation. The first level entrance opens to a cavernous entry with constructed-in desk, bookshelves, broad library, mini refrigerator, TV/DVD and queen couch bed. There is a...

  • Avon
  • 3 Bedrooms
  • 3 Bathrooms
Kitty Hawk Surf Co.

Experience more adventure, fun, and style with Kitty Hawk Surf Company. As the trusted Outer Banks retailer for all top surf and lifestyle brands, including, Hurley, Billabong, RVCA, The North Face, Patagonia, Salt Life, Salty Crew, Volcom...

WAALKES COTTAGE

“Waalkes Cottage” Come WALK with us directly out to the ocean, and enjoy the breathtaking views from the sun and dune decks of this OBX Oceanfront home. This cozy four bedroom home has all the living space conveniently located on one level. Prop...

  • Southern Shores
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Corolla Wild Horse Tours

Corolla Wild Horse Tours knowledgeable guides will ensure you and your family have a great wild horse tour! Along the way the guides will stop and point out interesting sites and local history and details of the Corolla Wild Horses history. Be sure...

Blue Sky 58-F

Blue Sky is the ultimate family-friendly Corolla vacation rental! After a day at the beach, located at the end of the street approximately 600 feet away, everyone will enjoy playing in the 12x20 pool and soaking in the bubbling hot tub. Inside, six...

  • Corolla
  • 6 Bedrooms
  • 4 Bathrooms
6/13 - 6/20
$5,099  $5,399
$300 off
6/27 - 7/4
$5,397  $5,697
$300 off
Carolina Designs Realty

Plan your Outer Banks vacation with Carolina Designs! Browse our inventory of 350+ select Outer Banks vacation rentals located in the towns of Corolla, Duck, Southern Shores, Kitty Hawk, Kill Devil Hills, and Nags Head. Book online anytime, or reach...

Beauty & The Beach

Located in Corolla/ 5 Bedrooms/ 4 Full Bathrooms/ 1 Half BathroomStunning oceanfront home accessible by 4 x 4 car only! This home sits on a corner lot and offers direct beach access with alluring ocean vistas. Approximately 9.3 miles up the beach...

  • Corolla
  • 5 Bedrooms
  • 4 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...

806 | The Granda

What a beautifully decorated & comfortable vacation home! The "Granda" is a terrific Nags Head beach home that has everything your family will need for a grand time on the Outer Banks. A short walk to the beach & the Seven Sister's...

  • Nags Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 14
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.