2026 Sailing Tours Guide

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Jolly Roger

When you first catch sight of The Jolly Roger, you might be unsure exactly what to think of it. Since its conversion from a gas station/grocery store to a restaurant in 1972, The Jolly Roger has been anything but your ordinary Outer Banks...

5549 - Stingray Chalet

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Welcome to Stingray Chalet! This 7 bedroom, 7.5 bathroom Outer Banks vacation rental is perfect for those who want to...

  • Nags Head
  • 7 Bedrooms
  • 8 Bathrooms
The Mystic Jewel

Walk into this shop and you’ll be delighted by all the glittering and sparkling from the way the mirrors and lighting show off jewelry from over 100 different designers and local artisans. Artfully-designed cases line the walls, filled with...

JOURNEYS END

You will enjoy this rare classic Outer Banks beach house and great surf views throughout its spacious 2,100 square feet, with 1,100 square feet of decking, and ocean view covered porch with louvered privacy walls on each side. Enjoy nighttime...

  • Southern Shores
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
9/19 - 9/26
$3,031  $3,487
$456 off
9/26 - 10/3
$2,760  $3,168
$408 off
10/3 - 10/10
$2,819  $3,168
$349 off
10/17 - 10/24
$2,560  $2,813
$253 off
American Pie

Discover the best homemade ice cream and authentic made-from-scratch New York Style pizza the Outer Banks has to offer at American Pie in Kill Devil Hills. An Outer Banks favorite for lunch, dinner or a delicious scoop of scrumptious ice cream after...

Sky's the Limit WHL-858

The Sky's the Limit at this spacious and airy oceanside home, providing everything you need for a perfect, relaxing Outer Banks vacation.Bring the whole family and settle into comfort and style in this spacious retreat. The top level great room...

  • Corolla
  • 6 Bedrooms
  • 6 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...

PENN STATION

A family favorite! Spacious and beautifully decorated, Penn Station offers the comforts and amenities of home. 2,950 square feet of living area and 1,900 square feet of decks provide ample room to relax and enjoy a carefree vacation in a lovely...

  • Southern Shores
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
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...

Aries

Located in Southern Shores / 7 Bedrooms / 5 Full BathroomsYour family will appreciate the expansive ocean vistas from this single level home on the Oceanfront in Southern Shores. Exterior amenities include an oceanfront sundeck with hot tub...

  • Southern Shores
  • 7 Bedrooms
  • 5 Bathrooms
9/5 - 9/12
$4,290  $4,915
$625 off
9/6 - 9/13
$6,242  $7,211
$969 off
9/15 - 9/22
$5,010  $5,762
$752 off
Corolla Raceway

The Ultimate Go Kart Racetrack That Kids and Adults will Enjoy! Corolla Raceway is the premier Go-Kart experience. Our upscale facility is designed to provide a first class entertainment experience. Corolla Raceway provides the newest Single...

Sundance

Located in Corolla / 6 Bedrooms / 4 Full Bathrooms / 1 Half BathroomGet ready for a memorable visit to the beach in this roomy home with plenty of space and broad decking. One of the few homes located on the oceanside of Corolla Light that can...

  • Corolla
  • 6 Bedrooms
  • 4 Bathrooms
Big Buck's Homemade Ice Cream

Serving our customers on the Outer Banks since 1994, Big Buck's ice Cream is dedicated serving you “The Best.” We offer a full line of super-premium ice cream products, smoothies, chocolates, and custom-made ice cream cakes! 2 locations...

Sand N'at

OCEANSIDE Frisco — Ships Timbers Rd. – Even the quietest retreats harbor a certain level of noise — the gentle call of seagulls, the waves breaking on the shore — that remind you of exactly where you are. Can you hear it? Then SAND N’AT is...

  • Frisco
  • 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.

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...