2026 Nags Head Sailing Tours Guide

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Paradise Dolphin Cruises

With the best views around and the quickest access to dolphins, Paradise Dolphin Cruises is committed to offering you one of the most amazing experiences of your life! Climb aboard the Kokomo, our 34-passenger catarmaran and the area’s newest...

DREAM ON THE BEACH

Plug your EV into the onsite charger, then follow the walkway to the sand at Dream On The Beach, an oceanfront Carolina Designs home at Milepost 17 in South Nags Head. Nine bedrooms, six kings, a 30-foot private pool, and a hot tub leave plenty...

  • Nags Head
  • 9 Bedrooms
  • 7 Bathrooms
Twiddy & Company

Twiddy & Company is here to provide all the help and southern hospitality you've come to anticipate when planning your beach vacation. We invite you to let us share our unique understanding of this coastal landscape; unlike any place in the...

STORK'S LANDING

6 full bathrooms serve just 5 bedrooms at Stork's Landing, and an elevator carries you and your luggage to every floor of this oceanfront Duck home from Carolina Designs. A 32 by 14 foot private pool and a hot tub on the covered deck fill the...

  • Duck
  • 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...

POSITIVE LATITUDE

“Positive Latitude” is one level living at its finest! This bright and open Outer Banks Vacation home has a spacious floor plan. You will find beautiful furnishings and decor with many upscale features! A Private pool will be the highlight of...

  • Southern Shores
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
9/26 - 10/3
$2,192  $2,506
$314 off
10/3 - 10/10
$2,192  $2,506
$314 off
10/31 - 11/7
$1,798  $1,892
$94 off
11/7 - 11/14
$1,648  $1,892
$244 off
11/14 - 11/21
$1,741  $1,892
$151 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...

TURTLE TALES

“Turtle Tales” will have you and your family feeling relaxed and rejuvenated! This beautiful, pet-friendly home in the highly sought after Chicahauk community offers a location where you will enjoy the benefits of bike paths, walking paths...

  • Southern Shores
  • 6 Bedrooms
  • 6.5 Bathrooms
  • Sleeps 12
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...

Driftwood

OCEANFRONT Avon - Beachcomber Drive - Consider this beach treasure a while and your mind will start its journey. Watch the colors of sunrise or a graceful formation of pelicans from this marvelous setting. Lots of decking, well appointed...

  • Avon
  • 4 Bedrooms
  • 3 Bathrooms
The Christmas Shop

Discover gifts, garlands and glittering lights galore. Looking for a trinket for someone who has everything? Choose ornaments for every hobby, occupation, occasion or enthusiast; from the fisherman or Disney lover; dancer or photographer. Throughout...

Salt and Soul Cottage

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.Everything and More in a Prime LocationTucked within the oceanside, private, gated community of Buck Island, Salt and Soul Cottage delivers the ideal...

  • Corolla
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Sundogs

Sundogs is a happening spot open year round in Corolla. Along with good food, they feature a nightlife that includes Karaoke and Silent Disco! They have a full bar and a menu suited to a host of tastes. Starters include nachos, crab dip, wings and...

Summerwinds

SOUNDFRONT Rodanthe - Cross of Honor Way - Wind and watersport enthusiasts take note! This handsome home has a private boardwalk that leads you to your own private sandy soundfront beach and launch. Choose from four comfortable and warmly decorated...

  • Rodanthe
  • 4 Bedrooms
  • 3 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.