2026 Nags Head Sailing Tours Guide

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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...

Fearing

Fearing House - Oceanfront Luxury in Pine Island Limited Be among the first to experience the Fearing House, an extraordinary 12-bedroom oceanfront estate located in the exclusive Pine Island Limited community of Corolla.This brand-new construction...

  • Corolla
  • 12 Bedrooms
  • 13 Bathrooms
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...

POINTE EAST

Discover POINTE EAST in Nags Head—a Carolina Designs OBX vacation rental where oceanfront luxury meets multi-family comfort. This spacious 8-bedroom retreat features an elevator, private pool, hot tub, and recreation room, creating the...

  • Nags Head
  • 8 Bedrooms
  • 6.5 Bathrooms
Whalehead in Historic Corolla

The prestigious Whalehead in Historic Corolla has been a dominant attraction to Corolla visitors since it was renovated and opened to the public in 2002. As part of the Historic Corolla Park, the Whalehead in Historic Corolla serves as a northern...

169 | Blankenship

This beautifully decorated & furnished beach cottage was constructed in the traditional "Old Nags Head" architectural style w/an attention to detail that will ensure that you have a special Outer Banks Vacation. Located in South Creek Acres...

  • Nags Head
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Sleeps 10
Flip Flop Shops

Free Your Toes!®Live, work and play with your toes exposed® and the freedom of flip flops on your feet. 



OCEAN BREEZE

Carolina Designs invites you to OCEAN BREEZE, a Duck retreat with 7 bedrooms, private pool, hot tub, and elevator just 175 yards from beach access. This seaside vacation rental in Sea Pines subdivision delivers premium amenities including a...

  • Duck
  • 7 Bedrooms
  • 7 Bathrooms
Ben Franklin

Stop by Nags Head's Ben Franklin at Mile Post 10 on the Bypass where you will find everything you need for the beach! From Clothing, T-shirts and Swimwear to Boards, Chairs, Umbrellas and Tackle. You'll find it all…and of course, we have the...

2381 - Peaceable Kingdom by the Sea

Always Included, complimentary linens and made beds! Unmatched panoramic views of the Ocean and Currituck Sound from this charming Outer Banks townhome located in Sanderling next door to the...

  • Duck
  • 2 Bedrooms
  • 2.5 Bathrooms
Jockey's Ridge State Park

Jockey's Ridge State Park is an unmistakable landmark for Nags Head vacationers and virtually everyone passing through along the main beach bypass, US 158. This park is marked by its towering sand dunes, which reach 80' - 100' feet tall and look...

SOUTHERN BELLE

Southern Belle is a gorgeous oceanside beach home, located in convenient Southern Shores on a quiet and private street, just a short walk to the beach! The house is beautifully decorated and has multi-level decks with built-in seating. Hardwood...

  • Southern Shores
  • 7 Bedrooms
  • 8 Bathrooms
  • Sleeps 14
8/22 - 8/29
$4,441  $6,991
$2,550 off
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...

5376 - Wench's Pad 2

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! NEW FOR 2026: Fitness room will become an additional bedroom. Door will be added to the existing Level 1 Master Bath...

  • Kill Devil Hills
  • 13 Bedrooms
  • 14 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.