2026 Nags Head Sailing Tours Guide

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082 | Carolina Tradewinds

Carolina Tradewinds is a fantastic Pet-Friendly, Oceanfront home with an Elevator, Private Pool and Extra Large Kitchen that provides quality finishes throughout and Amazing Ocean Views. Ideally situated in South Nags Head where beaches are wide...

  • Nags Head
  • 8 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
Bob's Wild Horse Adventure Tours

Welcome to Bob’s Wild Horse Adventure Tours, Corolla’s #1 source for family fun since 1996 and voted Best Wild Horse Tour in the Reader's Choice BEST of OBX contest! We offer guided tours to see the Corolla Wild Horses in several ways...

Never Forgotten

OCEANFRONT Resort Rodanthe - You’ll always remember NEVER FORGOTTEN, a vacation getaway with gorgeous ocean vistas that will linger in your mind long after your vacation is over. Take the elevator to the top level and enter into the roomy kitchen...

  • Rodanthe
  • 2 Bedrooms
  • 2 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...

818 | Unique

This home is centrally located to all that the Outer Banks has to offer. There are many choices nearby for dining, shopping, & fun entertainment. Public Beach access points are easily accessible within a half a mile. Water sports like kayaking...

  • Nags Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
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...

Group Therapy

Located in Southern Shores / 7 Bedrooms / 5 Full Bathrooms / 2 Half BathroomsConstructed in 2014, this home offers everything your family will want for your next Outer Banks get-away! Located in the community of Southern Shores on the Oceanside this...

  • Southern Shores
  • 7 Bedrooms
  • 5 Bathrooms
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...

Raspberry Duck

“Memories of vacations at the beach stay with you for a lifetime”….that’s the motto of the Raspberry Duck and we’ve designed and furnished it to give you and your family the ultimate family vacation. The home is located in Duck’s premier...

  • Duck
  • 6 Bedrooms
  • 6 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...

7570 - Robin's Nest

BEACH GEAR RENTALS INCLUDED! Always Included, complimentary linens and made beds! NEW FOR 2025: Replace fire pit. Welcome to Robin's Nest, a charming and cozy getaway in Avon. This 3-bedroom...

  • Avon
  • 3 Bedrooms
  • 3 Bathrooms
The Farmer's Daughter

Founded in 1984 on the coast of the Outer Banks, NC, Farmer’s Daughter still remains a destination for people wanting great quality, outstanding selection of unique clothing, accessories, and gifts at affordable prices. Committed to offering...

FIVE O CLOCK SOMEWHERE

Relax and enjoy every special moment that you and your family spend in this 3,600 square foot, five bedroom, upscale home. A beautifully appointed home with wonderful views, Five O’Clock Somewhere sits on a spacious lot (2/3 acre) in one of the...

  • Southern Shores
  • 5 Bedrooms
  • 5.5 Bathrooms
  • Sleeps 12
9/6 - 9/13
$2,430  $3,048
$618 off
9/13 - 9/20
$2,203  $2,754
$551 off
9/20 - 9/27
$2,300  $2,754
$454 off
10/11 - 10/18
$2,300  $2,754
$454 off
10/18 - 10/25
$2,037  $2,326
$289 off
10/25 - 11/1
$2,050  $2,326
$276 off
11/1 - 11/8
$1,939  $2,176
$237 off
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.