2026 Sailing Tours Guide

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KEES Vacations

KEES Vacations offers the best Outer Banks rentals for family vacations, romantic weekend getaways and groups of all sizes looking for the perfect OBX rental for their stay. When booking with KEES Vacations, travelers can expect excellence in...

Freebird

Discover Your Personal Slice Of Paradise At This Stunning Oceanfront Cottage Escape to "Freebird" in South Nags Head, a cozy coastal retreat where every moment is a promise of relaxation and rejuvenation. Bask in the breathtaking panoramic ocean...

  • Nags Head
  • 5 Bedrooms
  • 3 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...

Star Fish WHL-936

Star Fish is a splendid eight bedroom home just a few blocks from the beach in Whalehead section of Corolla. Featuring partial ocean and sound views from the top-level deck and a prime location, you’ll never want to leave Star Fish. The chef in...

  • Corolla
  • 8 Bedrooms
  • 7.5 Bathrooms
9/12 - 9/19
$3,812  $5,012
$1,200 off
9/19 - 9/26
$3,806  $4,806
$1,000 off
Risky Business Shrimping and Crabbing

If you’re looking for a fun, hands-on activity that the whole family can enjoy together, hop aboard Risky Business for an Outer Banks shrimping and crabbing charter. Our experienced captain and mate will show your group how to pull crab pots...

Aqua Holic

Located in Corolla / 5 Bedrooms / 4 Full Bathrooms / 1 Half BathroomArrive early and appreciate a Currituck Club pre-arrival experience at the main pool between 10 am and 4 pm! Games, trolley service to and from the beach, music, wine, food &...

  • Corolla
  • 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...

Second Wind Avon

SEMI-OCEANFRONT Avon – Pamlico Ct. – With ocean to sound vistas, SECOND WIND AVON will give you the vacation boost you need. This home is located in the idealistic north end of Avon and is a short walk to the beach. Appreciate the salty air on...

  • Avon
  • 5 Bedrooms
  • 3 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...

relax

Located in Corolla/ 5 Bedrooms/ 4 Full Bathrooms/ 1 Half BathroomThis home is equipped with all of the amenities you'll need to make your OBX vacation really enchanting including a huge pool, broad yard, new hot tub, quality gas grille, wine bar...

  • Corolla
  • 5 Bedrooms
  • 4 Bathrooms
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...

1772 - Dunes and Roses

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Relax in your own Oceanside oasis at Dunes and Roses in Corolla. This six bedroom home is well-equipped for your Outer...

  • Corolla
  • 6 Bedrooms
  • 6.5 Bathrooms
Jumpmasters OBX

Now with Axe Throwing! Jumpmasters OBX is the ultimate trampoline park on the Outer Banks with attractions the entire family will enjoy. From open jump trampolines to the dodgeball court, 3-D climbing wall, a foam pit, an epic ninja obstacle course...

Dunescape

Located in Corolla / 5 Bedrooms / 5 Full Bathrooms / 2 Half BathroomsPerched high on a dune with handsome ocean vistas with direct beach access! Located adjacent to the beach walkway just 450 feet from the beach. Ground Level: Exterior amenities...

  • Corolla
  • 5 Bedrooms
  • 5 Bathrooms
9/5 - 9/12
$2,801  $3,522
$721 off
9/26 - 10/3
$2,134  $2,633
$499 off
10/7 - 10/14
$2,134  $2,633
$499 off
10/13 - 10/20
$1,741  $2,109
$368 off
10/19 - 10/26
$1,741  $2,109
$368 off
10/26 - 11/2
$1,741  $2,109
$368 off
Nor'Banks Sailing & Watersports

Nor'Banks Sailing & Watersports beautiful location and top-of-the-line equipment, together with a friendly and professional staff make it one of the premier water sports centers on the Outer Banks. Nor'Banks' sound front location has a huge grassy lawn, restrooms, showers, a 200 foot pier and plenty of room for you to spend the day. Since 1979 Nor'Banks has been one of the finest sailing operations on the East Coast offering Flying Scots, Hobie Cats and quality private sailing instruction...

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.