2026 Nags Head Sailing Tours Guide

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The Cotton Gin

For those traveling to the Outer Banks, The Cotton Gin is a beloved landmark with its large windmill and picturesque gardens. The Cotton Gin has stood in the same location since 1929, starting as a working cotton gin and growing to a gift store with...

TWINSCAPE

“Twinscape,” your dream oceanfront escape nestled in the heart of Duck. Located at the end of a quiet cul-de-sac in the Bias Shores subdivision and just south of the Village of Duck. Enjoy all the community has to offer including a community...

  • Duck
  • 5 Bedrooms
  • 5.5 Bathrooms
  • Sleeps 10
8/8 - 8/15
$6,734  $7,819
$1,085 off
Firehouse Boil Delivery

DIY Seafood Boil Don’t Just Make Dinner, Make An Experience! We Deliver on the Outer Banks! Same Day Delivery! Make lasting memories by doing something new with friends and family. Why wait in line at a grocery store or restaurant? Our Low...

OSPREYS CATCH

Water views surround “Osprey’s Catch”, a spacious oceanside Outer Banks home located high on a hill just a mile north of the town of Duck. This home is characterized by panoramic sound views to the west and ocean views to the east from the...

  • Duck
  • 8 Bedrooms
  • 6.5 Bathrooms
  • Sleeps 16
8/22 - 8/29
$4,974  $5,736
$762 off
8/29 - 9/5
$4,309  $4,954
$645 off
9/5 - 9/12
$3,976  $4,563
$587 off
9/12 - 9/19
$3,552  $4,081
$529 off
9/19 - 9/26
$3,568  $4,081
$513 off
9/26 - 10/3
$3,658  $4,081
$423 off
10/10 - 10/17
$3,658  $4,081
$423 off
10/17 - 10/24
$2,969  $3,298
$329 off
10/24 - 10/31
$3,134  $3,298
$164 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...

7913 - Southern Comfort

Always Included, complimentary linens and made beds! Southern hospitality awaits you at Southern Comfort. Located in the heart of Hatteras, this oceanfront Outer Banks vacation home is perfect for...

  • Hatteras
  • 3 Bedrooms
  • 3 Bathrooms
Flip Flop Shops

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



2952 - Davis

Always Included, complimentary linens and made beds! Colony by the Sea, Unit B-209. Comfortably decorated and fully equipped with your family in mind. Your family is sure to enjoy this second floor...

  • Duck
  • 1 Bedrooms
  • 1 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...

831 | Lion At The Shores

Southern Shores-Oceanside. Private Pool, Hot Tub, Pet Friendly Comfortable, spacious and nicely decorated, Lion At The Shores is a pet friendly home that offers the luxury of having your own Private Swimming Pool, Hot Tub, Rec. Room, Pool Table...

  • Southern Shores
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
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...

Queen Anne's Revenge II 51-C

Everyone in the family will enjoy staying at Queen Anne's Revenge II, a pirate-themed, pet-friendly Corolla vacation rental, located in the Ocean Sands community. With great ocean views from the sun deck and located just 300' from the beach access...

  • Corolla
  • 4 Bedrooms
  • 2 Bathrooms
Sound Feet Shoes

Sound Feet Shoes is family owned and operated. Sound Feet has been in the retail shoe business for over 72 years, opening their first store in 1953. They provide the best customer service and are the only Outer Banks’ area full service shoe...

5711 - OBX TA SEA

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! PET FRIENDLY FOR 2027! NEW FOR 2026: All new vinyl decking. All TVs are Smart TVs with Hulu Live TV (Streaming only)...

  • Nags Head
  • 5 Bedrooms
  • 5.5 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.