2026 Sailing Tours Guide

Outer Banks Map
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Henry's Restaurant

Henry's Restaurant offers down home, simple food done Outer Banks style. Henry's Restaurant has been serving the Outer Banks of North Carolina since the summer of 1989. They are pleased to be considered one of the most popular restaurants in Dare...

In Spite of Ourselves

OCEANSIDE Waves — Sea Isle Hills Dr. — In spite of trying to find a reason to continue your search for a vacation rental, IN SPITE OF OURSELVES just may make you stop right here. Located nearly equal distance from both the ocean and Pamlico...

  • Waves
  • 4 Bedrooms
  • 4 Bathrooms
Miller's Seafood and Steakhouse

Miller's Seafood & Steakhouse has been a favorite among locals and visitors for more forty years. Offering delicious southern cuisine for both breakfast and dinner in a casual family atmosphere infused with coastal flair, it's no wonder this...

1537 - Carolina Sunset

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Beautifully redone Outer Banks vacation home in Monteray Shores, oceanside with breathtaking sunset views. Freshly...

  • Corolla
  • 6 Bedrooms
  • 6.5 Bathrooms
Gray's

Gray’s Outer Banks Lifestyle Clothing Company offers the absolute best in Outer Banks T-shirts and Sweatshirts including Champion, Under Armour with "Outer Banks” and Gear! We carry quality fashions and accessories for the whole family...

7589 - Anchored in the Sand

Always Included, complimentary linens and made beds! Anchored In The Sand is a charming 3-bedroom, 2-bathroom vacation rental located in Avon, North Carolina. Nestled on the oceanside, this Outer...

  • Avon
  • 3 Bedrooms
  • 3 Bathrooms
TRiO Restaurant & Market

Wine, beer and cheese lovers will love TRiO, an exciting retail and tasting destination in Kitty Hawk. Both a gourmet retail wine, beer and cheese shop as well as a bistro with a wine bar and tap house, TRiO offers the best of the worlds of...

Knot A Problem

Located in Corolla / Bedrooms / 5 Full Bathrooms / 2 Half BathroomsWhether you prefer to take a walk on the beach, swim in the private pool, stargaze from the hot tub or just relax on the deck, the amenities extended by this beach vacation home is...

  • Corolla
  • 6 Bedrooms
  • 5 Bathrooms
9/28 - 10/5
$3,876  $4,237
$361 off
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...

Coastin' KIN-58

This is your personal paradise on gorgeous Hatteras Island! Stunning sound views are yours from the large decks of Coastin', formerly known as Fish Tales. After a long day at the beach, relax with family and friends as you experience a breathtaking...

  • Avon
  • 6 Bedrooms
  • 7.5 Bathrooms
8/22 - 8/29
$4,772  $5,304
$532 off
Jolly Roger

When you first catch sight of The Jolly Roger, you might be unsure exactly what to think of it. Since its conversion from a gas station/grocery store to a restaurant in 1972, The Jolly Roger has been anything but your ordinary Outer Banks...

PERIWINKLE BEACH

Periwinkle Beach is the perfect location for rest and relaxation. This 4-bedroom, 2.5 bath home is located on the oceanside of Southern Shores. Periwinkle Beach is nestled within the sanctuary of mature live oaks, on a quiet street, with no need to...

  • Southern Shores
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 8
8/23 - 8/30
$2,477  $3,125
$648 off
8/30 - 9/6
$2,174  $2,604
$430 off
9/6 - 9/13
$1,899  $2,241
$342 off
9/20 - 9/27
$1,594  $1,882
$288 off
9/27 - 10/4
$1,503  $1,723
$220 off
10/4 - 10/11
$1,531  $1,723
$192 off
10/11 - 10/18
$1,547  $1,723
$176 off
10/18 - 10/25
$1,352  $1,477
$125 off
10/25 - 11/1
$1,352  $1,477
$125 off
11/1 - 11/8
$1,202  $1,326
$124 off
11/8 - 11/15
$1,212  $1,326
$114 off
11/15 - 11/22
$1,274  $1,326
$52 off
11/22 - 11/29
$1,274  $1,326
$52 off
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...

5243 - Going to Carolina

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Experience the ultimate beach getaway at Going to Carolina. This oceanfront Kill Devil Hills vacation rental is...

  • Kill Devil Hills
  • 10 Bedrooms
  • 11.5 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.

Nor'Banks Sailing & Watersports

Nor'Banks Sailing & Watersports beautiful location and top-of-the-line equipment, together with a friendly and professional staff make it one of the premier water sports centers on the Outer Banks. Nor'Banks' sound front location has a huge grassy lawn, restrooms, showers, a 200 foot pier and plenty of room for you to spend the day. Since 1979 Nor'Banks has been one of the finest sailing operations on the East Coast offering Flying Scots, Hobie Cats and quality private sailing instruction...