2026 Sailing Tours Guide

Outer Banks Map
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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...

The Brown Pelican 228

Enjoy a carefree vacation at The Brown Pelican, a nicely furnished vacation home near milepost 3 in Kitty Hawk boasting ocean views from the top level deck!The Brown Pelican offers a comfortable living area, a well-equipped kitchen, 3 cozy bedrooms...

  • Kitty Hawk
  • 3 Bedrooms
  • 2 Bathrooms
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...

THE SANDMAN

Overview For a memorable vacation, The Sandman offers invigorating ocean views and tranquil sound vistas from this Nags Head oceanfront retreat. Amenities include a central elevator, private suites, an expansive great room, a fully...

  • Nags Head
  • 6 Bedrooms
  • 7 Bathrooms
Fish Heads Bar and Grill

Rustic waterfront pub at a fishing pier with a large deck for seafood eats, draft beer & live music. Fish Heads Bar and Grill is THE tiki bar of the Outer Banks. Located at Mile Post 18.5 in Nags Head, we offer a view that is second to none...

Leap of Faith

Leap of Faith – Family Fun in Corolla’s 4x4 BeachesGet ready for an Outer Banks vacation that feels like an adventure from the moment you arrive! Located in the wild and beautiful 4x4 area of Corolla, Leap of Faith is only accessible by 4WD...

  • Carova
  • 5 Bedrooms
  • 6 Bathrooms
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...

MARIAH

Looking for a private escape? You will find it in Mariah, an exceptional, light-filled home in Chicahauk on one of Southern Shores most sought after streets. Lovely, live oaks offer privacy and seclusion, less than a ten-minute walk from the beach...

  • Southern Shores
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 8
6/7 - 6/14
$1,695  $1,901
$206 off
6/14 - 6/21
$1,818  $2,046
$228 off
Surf Side Hotel

Our oceanfront hotel rooms in Nags Head, North Carolina provide the absolute best views of the Atlantic Ocean! In addition to the gorgeous view, we also offer a great selection of amenities to our guests, including hot tubs, indoor and outdoor...

A SENSE OF PORPOISE

Major Renovations for 2026 include: brand new kitchen, remodeled baths and new LVP flooring in main living areas - New Photos coming soon! Discover your ultimate Outer Banks escape at “A Sense of Porpoise,” a beautifully appointed oceanfront...

  • Southern Shores
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Sleeps 8
6/6 - 6/13
$5,587  $6,151
$564 off
6/13 - 6/20
$5,880  $6,477
$597 off
6/27 - 7/4
$6,480  $7,143
$663 off
8/8 - 8/15
$5,742  $5,817
$75 off
Bonner Bridge Pier

Opened in 2021, the Bonner Pier is one of the more unique piers along the Outer Banks, as the 1,000-ft. long concrete structure was once the southern terminal of the original Bonner Bridge. Once the bridge was replaced by the new Basnight Bridge, a...

COOL AZUL

This charming oceanside home will bring you back year after year to spend quality time with the family, renew your spirit and enjoy all that the beautiful Outer Banks have to offer.Level 1:4 bedrooms (1 with Queen, TV/DVD player; shared full...

  • Southern Shores
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
5/15 - 5/22
$2,079  $2,273
$194 off
5/29 - 6/5
$2,875  $3,284
$409 off
8/14 - 8/21
$3,083  $3,363
$280 off
8/21 - 8/28
$2,713  $3,081
$368 off
8/28 - 9/4
$2,504  $2,762
$258 off
9/4 - 9/11
$2,359  $2,559
$200 off
Jockey's Ridge State Park

Jockey's Ridge State Park is an unmistakable landmark for Nags Head vacationers and virtually everyone passing through along the main beach bypass, US 158. This park is marked by its towering sand dunes, which reach 80' - 100' feet tall and look...

Golden Goose CD-102

Looking for an unforgettable Outer Banks vacation? Family memories are waiting to be made at Golden Goose! Receive FREE pool heat on any full-week stay in May!Enjoy beautiful 360-degree sound and ocean views from the crow's nest at this...

  • Duck
  • 6 Bedrooms
  • 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...