2026 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...

367-B | Double Dog Dare

OCEANFRONT - NAGS HEAD. Rent #367-A and #367-B together for a Total of 8 Bedrooms.Enjoy sweeping ocean views and relaxed coastal decor at this classic oceanfront duplex in Nags Head. The north-side unit is warm, family-friendly, and dog-friendly so...

  • Nags Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
6/20 - 6/26
$4,395  $4,995
$600 off
6/27 - 7/3
$4,895  $5,495
$600 off
7/4 - 7/10
$4,795  $5,495
$700 off
8/15 - 8/21
$3,495  $3,895
$400 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...

SUNRISE

Overview Book your next OBX stay at Sunrise, a four bedroom, semi-oceanfront vacation home at milepost 5 with views of the ocean, a private pool and hot tub, and a convenient beach access less than 100 yards to the south. Designed to...

  • Kill Devil Hills
  • 4 Bedrooms
  • 5.5 Bathrooms
Awful Arthur's Oyster Bar

Welcome to the home of the happy oyster where for over 40 years the oyster has been our world. The Outer Banks only authentic oyster bar is the place to enjoy sensational fare from the sea washed down with your favorite brew or cocktail. We serve by...

Knot for Sail

Step into Knot for Sail, a soundfront home that perfectly blends coastal elegance with unparalleled comfort. The spacious living room is bathed in natural light from expansive windows and offers sweeping views and plush seating around a modern...

  • Duck
  • 5 Bedrooms
  • 4.5 Bathrooms
Ben Franklin

Stop by Nags Head's Ben Franklin at Mile Post 10 on the Bypass where you will find everything you need for the beach! From Clothing, T-shirts and Swimwear to Boards, Chairs, Umbrellas and Tackle. You'll find it all…and of course, we have the...

THE HIGH TIDER

Overview New to the Carolina Designs program for the 2027 season!Located on the oceanfront in Nags Head just south of Jennette's Pier, The High Tider offers vacation comforts, coastal style, and unforgettable views to all who stay. A private...

  • Nags Head
  • 8 Bedrooms
  • 9.5 Bathrooms
Twiddy Wedding Homes

Celebrate your love in a place you love! Twiddy & Company has a wide variety of wedding homes located throughout the Outer Banks. Find the perfect special event home for your Outer Banks wedding, whether you're planning an intimate elopement or...

Life is Good

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.“Life is Good” at this lovely beach cottage. Homeowners have lovingly updated over the years, careful to keep the charm and character of the...

  • Corolla
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
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...

Afishynado CP-74

Afishynado is your dream Corolla Outer Banks vacation rentals, offering a perfect getaway for your family or group. This luxurious and vibrant vacation rental is designed to exceed all your expectations! Nestled in the heart of Corolla, NC, this...

  • Corolla
  • 7 Bedrooms
  • 4.5 Bathrooms
Surf Side Hotel

Our oceanfront hotel rooms in Nags Head, North Carolina provide the absolute best views of the Atlantic Ocean! In addition to the gorgeous view, we also offer a great selection of amenities to our guests, including hot tubs, indoor and outdoor...

Beach Please QUAY-B3

Beach Please invites you to relax and recharge in style at this gorgeous oceanfront retreat! Located in the heart of Nags Head, this charming three-bedroom, three-bath, multi-level condo offers breathtaking ocean views, unbeatable beach access, and...

  • Nags Head
  • 3 Bedrooms
  • 3 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...