2026 Kill Devil Hills 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...

Ocean Dream On 639

Experience the ultimate beachside getaway at Ocean Dream On, a stunning vacation rental located just steps from the beach in the heart of South Nags Head. With a panoramic ocean view from your private deck, complete with a luxurious hot tub for...

  • Nags Head
  • 4 Bedrooms
  • 3 Bathrooms
8/22 - 8/29
$3,477  $3,977
$500 off
9/5 - 9/12
$2,888  $3,388
$500 off
9/12 - 9/19
$2,903  $3,403
$500 off
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...

Sugar Magnolia

Located in Corolla / 5 Bedrooms / 5 Full Bathrooms / 1 Half BathroomLocated Oceanside in Corolla Light, this striking home has everything you'll need for a great Corolla vacation! Your family will appreciate being able to walk to the Ocean, the...

  • Corolla
  • 5 Bedrooms
  • 5 Bathrooms
Sun Realty

Sun Realty offers the Best Selection of Vacation Rentals on the Outer Banks. Our large selection of Outer Banks rentals means you can choose from a wide range of amenities, including private swimming pools, hot tubs, theater rooms, game rooms, pet...

606 | The Wright View

Great Ocean Views and Direct Access to the Beach await when You Choose this Wonderful Kitty Hawk Vacation Home for Your Family Vacation. Beautifully Decorated and Furnished, Nothing has been overlooked to ensure a Grand Time on the Outer Banks...

  • Kitty Hawk
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Sleeps 10
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...

Place in the Sun

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.Find a “Place in the Sun” at this lovely destination for your Outer Banks beach vacation! New owners have refreshed a nice beach house into a breezy...

  • Corolla
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
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...

157 | No Problem

This comfortable family vacation cottage has a great location that is approximately 250 feet from the beach access in Kill Devil Hills (sand path is located on south side of home & you must cross the Beach Road to get to the path over the...

  • Kill Devil Hills
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
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...

7657 - Dragon's Lair

Always Included, complimentary linens and made beds! NEW SATURDAY TURN FOR 2026! NEW FOR 2025: Enclosed screen porch and replace outside stairway connecting porch to ground. Welcome to Dragon's...

  • Avon
  • 3 Bedrooms
  • 3 Bathrooms
Poke Box

PokeBox offers fresh, quick, simple, healthy poke bowls in Nags Head. Choose your items and build your bowl. Tuna, salmon, chicken, steak, shrimp and tofu options available. Mix in your favorite veggies, sauces and toppings for the perfect poke...

Flip Flop'n 97-K

Flip Flop’n is a stunning oceanside retreat in the sought-after Section K of Ocean Sands, Corolla, designed for both relaxation and fun. Perfect for active families, this home features a basketball goal, air hockey, and horseshoes, plus multiple...

  • Corolla
  • 5 Bedrooms
  • 3.5 Bathrooms
6/27 - 7/4
$4,543  $5,043
$500 off
7/4 - 7/11
$4,543  $5,043
$500 off

Sail the Outer Banks (formerly Outer Banks Sailing Academy) offers professional sailing instruction operating under the standards of the American Sailing Association. They offer lessons in Kill Devil Hills. The Academy presents an array of classes...