2026 Nags Head Sailing Tours Guide

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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...

Funtiki

Come enjoy the peace & tranquility that this wonderful South Nags Head vacation home provides. Sip a cool drink on the back deck while you enjoy the breathtaking sunsets that fall over the pristine natural parklands of the Cape Hatteras National...

  • Nags Head
  • 7 Bedrooms
  • 5 Bathrooms
Pigman's Bar-B-Que

You haven’t experienced North Carolina until you’ve experienced North Carolina BBQ, and Pigman’s Bar-B-Que offers excellent North Carolina BBQ meals served with southern hospitality. Pigman’s offers traditional eastern...

Castle on a Cloud

High on the rooftop deck enjoying panoramic ocean views, you will find yourself in “Castle on a Cloud”. Imagine your family in a beautifully decorated beach house with comfortably appointed pool area and shaded picnic and play area for you and...

  • Southern Shores
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
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...

WBD Whalebone Oceanside 4 Bedroom Cottag...

Welcome to Whalebone Oceanside Cottage D by KEES Vacations! A classic Outer Banks experience with a fresh new chapter. Nestled in South Nags Head at Milepost 16.5, Whalebone Ocean Cottages brings the charm of a historic cottage court into the modern...

  • Nags Head
  • 4 Bedrooms
  • 4 Bathrooms
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...

HAKUNA MATATA

Enjoy a "NO WORRY" vacation in a private, treed setting. Pleasant 455-yard walk to beach access.Level 1:Powder room.Level 2:North side - 2 bedrooms (1 with Queen, CATV: opening to deck with swing and overlooking pool, connecting bath (with tub and...

  • Southern Shores
  • 5 Bedrooms
  • 3.5 Bathrooms
  • Sleeps 10
8/28 - 9/4
$2,179  $2,469
$290 off
9/4 - 9/11
$2,031  $2,296
$265 off
9/11 - 9/18
$1,793  $2,031
$238 off
9/18 - 9/25
$1,793  $2,031
$238 off
Captain Johnny's Dolphin Tours

Join Captain Stuart Wescott aboard The Captain Johnny boat for a Guaranteed Dolphin Watch cruise in protected waters off the Outer Banks, NC. This two hour cruise is ideal for all ages. Enjoy breathtaking views as you listen to a...

SEAPHORIA

Discover SEAPHORIA in Kill Devil Hills, a Carolina Designs OBX vacation rental where 12 bedrooms, each with a private bath, an elevator to every level, and a 41-foot private pool with a poolside hot tub set the stage for a large-group Outer...

  • Kill Devil Hills
  • 12 Bedrooms
  • 14 Bathrooms
ZoomAround Street Legal Golf Cart Rentals

ZoomAround Street Legal Golf Cart Rentals provides our communities and our visitors with fun, safe and convenient access to innovative transportation while providing an unparalleled customer experience. Don’t carry all of your beach gear...

SOUTHERN COMFORT IN DUCK

This home is located in the heart of the Village of Duck, 500 yards from private beach access (with parking). Each of the six bedrooms is uniquely decorated and offers a private bath and deck. The private pool, keeps the whole family entertained...

  • Duck
  • 6 Bedrooms
  • 6.5 Bathrooms
  • Sleeps 13
9/12 - 9/19
$3,251  $3,942
$691 off
9/19 - 9/26
$3,251  $3,942
$691 off
Corolla Wild Horse Fund

We are The Corolla Wild Horse Fund the non-profit 501 (c) (3) charity responsible for the care and protection of the wild Banker horses roaming the northernmost beaches of the Outer Banks. Join us in the summer season, every Wednesday morning from...

Duck R Way

This oceanside home features 5 bedrooms and 3 and a half baths with plenty of room for a large family. On the upper level you'll find the open great room with flat screen TV, access to the sun deck, dining area with table which seats 10 guests, a...

  • Duck
  • 5 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.