2026 Kill Devil Hills Sailing Tours Guide

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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...

108 | The Sandy Flip-Flop

5/4/26: Great things have happened for the 2026 season! A Private Salt Water Swimming Pool (Heat Option Available) is now in place, the East Side Decks have been replaced, an Outdoor Luggage / Grocery Lift has been constructed, and Hot Tub has been...

  • Kill Devil Hills
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 11
Mike Dianna's Grill Room

Welcome to Mike Dianna's Grill Room, home to the finest seafood, USDA prime beef, amazing live entertainment and more! Come have brunch or dinner with us in Corolla on the beautiful Outer Banks. Celebrating over 20 years in the Timbuck II Shopping...

K4002 Coastal Calling at Corolla Shores

Welcome to Coastal Calling at Corolla Shores! When the goal of your Outer Banks vacation is fun in the sun and games in the shade with a big group of your best peeps and family, this Corolla Shores home delivers! This 7-bedroom Oceanside home in the...

  • Corolla
  • 7 Bedrooms
  • 7 Bathrooms
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...

JOURNEYS END

You will enjoy this rare classic Outer Banks beach house and great surf views throughout its spacious 2,100 square feet, with 1,100 square feet of decking, and ocean view covered porch with louvered privacy walls on each side. Enjoy nighttime...

  • Southern Shores
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
9/19 - 9/26
$3,031  $3,487
$456 off
9/26 - 10/3
$2,760  $3,168
$408 off
10/3 - 10/10
$2,799  $3,168
$369 off
10/17 - 10/24
$2,560  $2,813
$253 off
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...

Klein Cottage

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.Bring your family to this classically beautiful oceanfront property with panoramic ocean views from inside and out! Historic properties have been...

  • Southern Shores
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Miss Oregon Inlet

Oregon Inlet Fishing Center is the home of the largest and most modern charter boat fishing fleet on the eastern seaboard. A full service marina in Nags Head NC, Oregon Inlet offers a comprehensive charter boat fishing experience for the "old salt...

Sandi Hill

The private pool keeps you cool, the hot tub soothes your troubles and the spacious furnished decks allow you to check out the views while enjoying ocean breezes. You can bring the family dog too! Great vacation memories are waiting to be made in...

  • Corolla
  • 6 Bedrooms
  • 4 Bathrooms
Brew Thru

No trip to the Outer Banks is complete without cruising through Brew Thru, the Outer Banks’ original drive thru convenience store. Whether you’re looking for a refreshing cold beverage of Coke, Pepsi and other soft drinks on the go...

Boardwalk

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.It’s time to play! “Boardwalk” offers a vacation spot for your large family gathering with plenty of room and activities for all! The private...

  • Kill Devil Hills
  • 12 Bedrooms
  • 10 Bathrooms
  • Sleeps 33
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...

Bernice's Dream

Located in Duck / 4 Bedrooms / 4 Full Bathrooms / 1 Half BathroomCavernous, handsomely appointed home providing complete comfort and convenience for your oceanside visit!Ground Level: Exterior amenities include a carport and covered entry, direct...

  • Duck
  • 4 Bedrooms
  • 4 Bathrooms

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...