2026 Sailing Tours Guide

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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...

A SOUND ESCAPE

This custom home is beautiful, unique and well-planned. Offering wonderful views of the sound, a private pool, and top-of-the-line furnishings and appointments. Witness one of those world-famous Outer Banks sunsets from the spacious sundecks. This...

  • Duck
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
8/30 - 9/6
$2,415  $2,890
$475 off
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...

Maughlin 532-A

If you are looking for a truly laid-back beach experience, Maughlin is the place! With the living area and porch overlooking the ocean, you almost forget you’re above dry land and able to walk the wide beach before getting your toes wet. This...

  • Nags Head
  • 3 Bedrooms
  • 1.5 Bathrooms
Black Pelican

Black Pelican oceanfront restaurant is one of the Outer Banks’ premier restaurants serving lunch and dinner daily. Black Pelican is where you can enjoy fresh seafood, steaks, vegetarian dishes, sandwiches and some of the barrier island’s...

5186 - Casa del Sol 3

Always Included, complimentary linens and made beds! New for 2025: New Decks East and West Side of Property. Casa Del Sol 3 features everything you need for an unforgettable OBX vacation. Located on...

  • Kill Devil Hills
  • 2 Bedrooms
  • 2.5 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...

5412 - Seaside Fun

Always Included, complimentary linens and made beds! This Signature Series home located on the cean side of the Virginia Dare Trail, Seaside Fun is nestled at the end of a quiet, secluded road and is...

  • Nags Head
  • 5 Bedrooms
  • 6 Bathrooms
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...

382 | Journey's End

6/21/26: Beach Nourishment has been completed in this area. Come and enjoy the refreshed beach! Journey's End is a modern Oceanfront home constructed in the traditional Old Nags Head architectural style. Boasting lovely décor, hardwood floors...

  • Nags Head
  • 7 Bedrooms
  • 5.5 Bathrooms
  • Sleeps 14
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...

What A View in Corolla

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.What A View in Corolla!  Climb up to the Crows Nest on the circular stairs to one of the highest points on the Outer Banks and you will understand the...

  • Corolla
  • 9 Bedrooms
  • 7 Bathrooms
  • Sleeps 19
KEES Vacations

KEES Vacations offers the best Outer Banks rentals for family vacations, romantic weekend getaways and groups of all sizes looking for the perfect OBX rental for their stay. When booking with KEES Vacations, travelers can expect excellence in...

CHASING THE DREAM

Overview You've arrived, and now it's time to relax and rejuvenate at Chasing The Dream, a charming seaside retreat designed and furnished with comfort and enjoyment in mind. Ease into peaceful vacation days as you enjoy morning coffee...

  • Corolla
  • 7 Bedrooms
  • 5.5 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...