2026 Nags Head Sailing Tours Guide

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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...

771 | Cabana

The Cabana is an exceptional Oceanfront property that provides a wide range of amenties to enhance your vacation experience. Amazing views of the Atlantic Ocean and high-end finishes are sure to please. Centrally located in Nags Head, this spacious...

  • Nags Head
  • 8 Bedrooms
  • 7.5 Bathrooms
  • Sleeps 16
5/9 - 5/15
$4,595  $5,195
$600 off
5/16 - 5/22
$5,995  $6,795
$800 off
5/23 - 5/29
$6,495  $7,495
$1,000 off
Coastal Home OBX

Distinctive, Authentic, Affordable Coastal Furniture & Design. Beach Living Furniture Line • Largest In-Stock Furniture Warehouse on the OBX • Professional Design Services. Transform your home—visit our showroom in Kill Devil...

BELLA

Overview Elevate your next vacation experience with a home designed to impress! Perched on a high oceanside dune offering ocean and sound vistas, Bella is a Tuscan-inspired retreat that evokes the upscale warmth and comfort one would...

  • Duck
  • 6 Bedrooms
  • 8 Bathrooms
Flip Flop Shops

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



Sounds Great R-213

Sounds Great, overlooking the Pamlico Sound, with its beautiful waters and kaleidoscopic skies, is the ideal place to start when looking for the perfect sunset. Grab a refreshing drink and head to any one of the three levels of furnished decks or...

  • Rodanthe
  • 6 Bedrooms
  • 6.5 Bathrooms
5/16 - 5/23
$2,723  $3,223
$500 off
6/20 - 6/27
$6,585  $7,785
$1,200 off
6/27 - 7/4
$7,601  $8,801
$1,200 off
8/8 - 8/15
$5,974  $7,174
$1,200 off
8/15 - 8/22
$5,363  $6,563
$1,200 off
8/22 - 8/29
$4,953  $5,703
$750 off
8/29 - 9/5
$4,342  $5,092
$750 off
H2OBX Waterpark

YOUR BEST SUMMER DAY - Nothing satisfies your craving for fun like a day at the H2OBX Waterpark. Start with that perfect Carolina sun. Add a dose of adrenaline as you soar 6 stories up on The Rogue Wave or drop 90 screaming feet down The Plank...

Tides Rollin' In

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.A Half Mile from EverythingStep into seaside style at this newly renovated Nags Head vacation rental! At milepost 11.5, Tides Rollin’ In offers the...

  • Nags Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Outer Banks Mall

Outer Banks Mall is a large outdoor shopping center featuring everything you need for sun, fun and shopping. Located at MP 14 in Nags Head, the large shopping center features a wide variety of food & beverage providers; everything from breakfast...

C112A - Happy Place

Always Included, complimentary linens and made beds! Enjoy the beauty of the Nags Head soundside at Happy Place! This beautiful Nags Head vacation condo is located on the first floor of Sugar Creek...

  • Nags Head
  • 2 Bedrooms
  • 2 Bathrooms
OBX Ghost Tours

OBX Ghost tours is something your family will be talking about the rest of the summer! You'll be entertained as a guide leads you through down town Manteo by lantern telling the spooky stories that makes The Outer Banks one of the most haunted...

Our Lighthouse

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.Guiding You to the Perfect OBX StayLocated in the Whalehead Community of Corolla, “Our Lighthouse” has everything you need for a fun-filled family...

  • Corolla
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
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 40-passenger catarmaran and the area’s newest...

Hook, Line and Skipper

Located in Corolla /6 Bedrooms / 5 Full Bathrooms / 1 Half BathroomReady to reel in the ideal Outer Banks hideaway? Welcome to OS11K, Hook, Line and Skipper, where coastal appeal meets ultimate convenience. While many beach units leave you trekking...

  • Corolla
  • 6 Bedrooms
  • 5 Bathrooms
8/1 - 8/8
$4,684  $5,131
$447 off
8/18 - 8/25
$3,857  $4,211
$354 off
8/25 - 9/1
$3,857  $4,211
$354 off

Kitty Hawk Kites’ Whalebone Watersports Center is your one-stop shop for Outer Banks water adventures. Located on the Nags Head-Manteo Causeway right on Roanoke Sound, this location offers it all – dolphin watching cruises with a marine...