2026 Nags Head Sailing Tours Guide

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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...

Surfsong

Classic OBX CondoSurfsong is a coastal condo perfect for a family beach escape. Nestled in the Indian Summer Condominium complex, this upper-level retreat blends the nostalgic feel of classic hardwood walls with updated decor for a clean and modern...

  • Corolla
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
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...

Sandy Paws

"Sandy Paws" is sure to be a favorite for your annual OBX vacation!  Sandy Paws features a great semi-oceanfront locations with great sunrise views.  There is a refreshing private pool that will please everyone!  The home features a family...

  • Kill Devil Hills
  • 5 Bedrooms
  • 4 Bathrooms
Sun Realty

Sun Realty offers the Best Selection of Vacation Rentals on the Outer Banks. Our large selection of Outer Banks rentals means you can choose from a wide range of amenities, including private swimming pools, hot tubs, theater rooms, game rooms, pet...

Duck Crossing at Pirates Cove

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.Canalfront Condo in Pirates Cove Marina CommunityDuck Crossing at Pirate's Cove is a beautifully decorated condo located in the gated Pirate’s Cove...

  • Nags Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
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...

Sunset Vista

Upgrades for 2026 include: new wood floor throughout entry and main levels, new carpet in upper-level master bedrooms, two remodeled bathrooms with walk-in showers. Located in Duck / 4 Bedrooms / 3 Full BathroomsSavor charming sunsets over...

  • Duck
  • 4 Bedrooms
  • 3 Bathrooms
9/7 - 9/14
$1,964  $2,143
$179 off
9/20 - 9/27
$1,737  $1,891
$154 off
9/27 - 10/4
$1,813  $1,975
$162 off
Brindley Beach Vacations

Brindley Beach Vacations offers premier Real Estate and Property Management services across the entire Outer Banks. Representing more than 450 vacation rental homes, we proudly serve every region—from the southern beaches of Hatteras Island...

Pier House

Experience the charm of "The Pier House," a unique oceanfront retreat just steps away from Jennette's Pier. This spacious and inviting home is designed with relaxation and family fun in mind, boasting breathtaking ocean views and a wide array of...

  • Nags Head
  • 5 Bedrooms
  • 5 Bathrooms
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...

Higher Ground 234-A

Welcome to Higher Ground, a gorgeous, one-of-a-kind custom home centrally located just steps from the sound in Kitty Hawk. This vibrant and unique coastal home offers classic character and fine details at every turn, including a reclaimed shipwreck...

  • Kitty Hawk
  • 5 Bedrooms
  • 4 Bathrooms
Miss Oregon Inlet

Oregon Inlet Fishing Center is the home of the largest and most modern charter boat fishing fleet on the eastern seaboard. A full service marina in Nags Head NC, Oregon Inlet offers a comprehensive charter boat fishing experience for the "old salt...

Thor at the Shore VICT-5

This oceanfront family-friendly Nags Head cottage has everything you need for a fun and relaxing Outer Banks vacation. Wake up early to watch the beach waves and sunrise from your oceanfront deck. Just steps away, across the private Viking Court...

  • Nags Head
  • 5 Bedrooms
  • 2.5 Bathrooms
8/22 - 8/29
$3,727  $4,427
$700 off
8/29 - 9/5
$3,649  $4,349
$700 off
9/12 - 9/19
$3,539  $4,239
$700 off
9/19 - 9/26
$3,283  $3,983
$700 off
9/26 - 10/3
$2,823  $3,523
$700 off
10/3 - 10/10
$2,591  $3,291
$700 off
10/10 - 10/17
$2,648  $3,348
$700 off
10/17 - 10/24
$2,504  $3,204
$700 off
10/24 - 10/31
$2,489  $3,189
$700 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.