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...

495 | Oriole's Perch

Relax and enjoy the beautiful Beaches of the Outer Banks from this nicely decorated and well-equipped Beach Home. Situated right on the Beach in South Nags Head, this home offers unparalleled views! After a day on the Beach, you can watch the Moon...

  • Nags Head
  • 4 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Flip Flop Shops

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



192 | The Last Resort

This lovely cottage sits right above the Beach and has Endless Ocean and Beach Views making this home an excellent choice for the small family vacation. Nicely decorated, well equipped, and very comfortable, this home has ocean facing decks on two...

  • Kitty Hawk
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Jimmy's Seafood Buffet

Home of the Crab Leg & Lobster Buffet for 27 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...

SONS OF THE SEA

Relax and enjoy this brightly decorated cottage which includes a private pool. Just a short stroll from the ocean (383 yards) with direct beach access. Very clean and comfortable home with amenities galore!Level 1:4 bedrooms (1 with Queen with TV...

  • Southern Shores
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 8
6/27 - 7/4
$2,825  $3,235
$410 off
8/22 - 8/29
$2,111  $2,394
$283 off
8/29 - 9/5
$1,877  $2,119
$242 off
9/5 - 9/12
$1,760  $1,981
$221 off
Resort Realty

For more than 39 years, Resort Realty has been providing unforgettable Outer Banks vacations. From Corolla to Hatteras Island, Resort Realty offers nearly 600 Outer Banks vacation homes that range from cozy 1-bedroom condos to exquisite 20-bedroom...

5188 - Casa Del Sol 6

Always Included, complimentary linens and made beds! New for 2025: New Decks East and West Side of Property. Nothing could be finer than a vacation in Carolina and nothing could be finer than the...

  • Kill Devil Hills
  • 2 Bedrooms
  • 2.5 Bathrooms
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...

Jake's Wake

OCEANVIEW Salvo - Colony Dr. - For a calming vacation that’s filled with sound and ocean vistas, steer into JAKE’S WAKE. Stroll down to the beach or relax outdoors by the shining private pool or in the private hot tub. Kick off the flip flops...

  • Salvo
  • 5 Bedrooms
  • 3.5 Bathrooms
Sundogs

Sundogs is a happening spot open year round in Corolla. Along with good food, they feature a nightlife that includes Karaoke and Silent Disco! They have a full bar and a menu suited to a host of tastes. Starters include nachos, crab dip, wings and...

South Beach CSC-4K

South Beach is located in the premier Croatan Surf Club condominium complex. A gorgeous top floor corner unit offering 3 bedrooms and 3 bathrooms offers breathtaking ocean views, with beautiful hardwood floors throughout the main living and dining...

  • Kill Devil Hills
  • 3 Bedrooms
  • 3 Bathrooms
Mike Dianna's Grill Room

Welcome to Mike Dianna's Grill Room, home to the finest seafood, USDA prime beef, amazing live entertainment and more! Come have brunch or dinner with us in Corolla on the beautiful Outer Banks. Celebrating over 20 years in the Timbuck II Shopping...

BEYOND THE SEA

Overview Experience easy beach living in this well-appointed Kill Devil Hills oceanfront estate with sweeping views of both the ocean and the Wright Brothers Monument. Beyond The Sea features 12 richly appointed bedrooms (10 with...

  • Kill Devil Hills
  • 12 Bedrooms
  • 13 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.