2026 Nags Head Sailing Tours Guide

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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...

Zen
Zen

SEMI-OCEANFRONT Waves — Sea Isle Hills Ct. — Discover your inner tranquility at ZEN, a six-bedroom/five-full and one-half-bath haven where both ocean and sound vistas diverge from the tranquility to compete for your attention. Bring your...

  • Waves
  • 6 Bedrooms
  • 5.5 Bathrooms
Flip Flop Shops

Free Your Toes!®Live, work and play with your toes exposed® and the freedom of flip flops on your feet. 



RETREAT

Charming and cozy one level classic oceanfront beach cottage.3 bedrooms (1 with Double, half bath; 1 with Double, 1 with Twins), 1 full bath (tub and shower). 2 bedrooms with ocean sunrise, picture window views. Open living area with eat-in...

  • Kitty Hawk
  • 3 Bedrooms
  • 1.5 Bathrooms
  • Sleeps 6
Surf or Sound Realty

Surf or Sound Realty invites you to explore our collection of over 600 premier vacation rental homes on Hatteras Island, featuring the largest selection of oceanfront accommodations. Nestled within the breathtaking Cape Hatteras National Seashore...

Sweet Tranquility

SOUNDFRONT Salvo - Otter Way - That excellent feeling of SWEET TRANQUILITY is just what you get from a vacation in this well-planned, extremely roomy and well-equipped soundfront home. The upper level offers fantastic expansive vistas from every...

  • Salvo
  • 6 Bedrooms
  • 6.5 Bathrooms
OBX Shipping Center

We are the only Authorized Shipping Center on the OBX for FedEx, UPS and DHL. Come to OBX Shipping Center for all your shipping and office needs. We offer Notary services, copies, faxing, laminating, among other office services. You do the...

DOLPHIN WATCH

Spacious Oceanview Retreat for up to 14 GuestsNew in May 2026, Dolphin Watch is a spacious, Tall Ship-inspired Outer Banks retreat designed for gathering, relaxing, and making memories together. With ocean views, generous indoor and outdoor living...

  • Southern Shores
  • 5 Bedrooms
  • 5.5 Bathrooms
  • Sleeps 14
10/30 - 11/6
$4,239  $4,778
$539 off
11/6 - 11/13
$4,088  $4,778
$690 off
11/13 - 11/20
$4,088  $4,778
$690 off
11/27 - 12/4
$4,465  $4,778
$313 off
12/4 - 12/11
$4,088  $4,778
$690 off
12/11 - 12/18
$4,088  $4,778
$690 off
Old Man Charters

  Experience the Outer Banks from the water with Old Man Charters, a personalized boat tour company based in the historic fishing village of Wanchese. Departing from a private dock on the southern end of Roanoke Island, Old Man Charters...

B1G McBoujee

Your Perfect Coastal Escape in Southern Duck! Escape to your ideal coastal retreat with this charming 2-bedroom vacation rental condo, boasting comfortable, stylish and updated decor. Nestled along the pristine shoreline in southern Duck, this...

  • Duck
  • 2 Bedrooms
  • 2 Bathrooms
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...

Paradise VI

Now available to book for 2027! Advance Reservations in this property for a future year more than 51 weeks in advance are allowed. Current year guests are not offered first right of refusal. Reserve any available 2027 week and pay 25% within 3...

  • Kill Devil Hills
  • 10 Bedrooms
  • 9 Bathrooms
Kitty Hawk Kites

Looking to fly a kite on the beach or atop the spectacular dunes of Jockey’s Ridge State Park? Kitty Hawk Kites offers the largest selection of kites, wind art, flags, games, and toys on the Outer Banks, with experts on staff to get you flying...

Windandsea R-11

Experience the best of the beach and soundside life at Windandsea! Access to both the ocean and sound is just a short distance away in either direction. The island here is less than half a mile across, so it's a short walk to enjoy the world-famous...

  • Rodanthe
  • 3 Bedrooms
  • 2 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.