2026 Nags Head Sailing Tours Guide

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Events
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Donutz on a Stick

Stay, Play and Eat- Donuts, Ice Cream & Coffee Treats! Located on the Duck Boardwalk, behind Dockside Seafood, this breakfast & Dessert-Shop features treats you've never tasted before! Try the hot, made to order, donutz...

Merlion Haven

SEMI-SOUNDFRONT Salvo — Wind Over Waves — With the grace of a mermaid and the heart of a lion, MERLION HAVEN pulls off the ideal balance as a sanctuary of calm and a base for energetic pursuits. Located in an fresh community of opulent homes...

  • Salvo
  • 6 Bedrooms
  • 7.5 Bathrooms
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...

K6101 Wright Play at Carolina Shores

Welcome to Wright Play at Carolina Shores by KEES Vacations! With its twist on classic modern style and amenities and amazing proximity to the ocean, Wright Play (Formerly The Bodie Island) has a style all its own. Reunite family and friends for...

  • Nags Head
  • 8 Bedrooms
  • 9 Bathrooms
The Cotton Gin

For those traveling to the Outer Banks, The Cotton Gin is a beloved landmark with its large windmill and picturesque gardens. The Cotton Gin has stood in the same location since 1929, starting as a working cotton gin and growing to a gift store with...

Miles of Treasure 434-A

Discover your family’s new favorite vacation destination at Miles of Treasure, a beautiful, semi-oceanfront home just steps from the beach. Enjoy stunning ocean views from this charming retreat, as well as the expanded living and dining areas...

  • Nags Head
  • 4 Bedrooms
  • 4 Bathrooms
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...

Dream Catcher CV-45

Offering all of the best amenities for the perfect Outer Banks vacation, Dream Catcher is a beautifully furnished rental home in the 4x4 beaches of Carova. Guests will love the private 14x32 pool and hot tub, as well as the views from the top level...

  • Carova
  • 5 Bedrooms
  • 4.5 Bathrooms
Carolina Designs

Plan your Outer Banks vacation with us! Browse our inventory of 350+ premier Outer Banks vacation rentals, including houses in Duck, Corolla, Southern Shores, Kill Devil Hills, Kitty Hawk, and Nags Head!

Turtle Watch

SOUNDSIDE Avon — Pony Pasture Dr. — New for 2026! — TURTLE WATCH is a relaxing haven as inviting and predictable as the ebb and flow of Avon’s tides. This three-bedroom/three- and one-half-bathroom home has the power to soothe the soul...

  • Avon
  • 3 Bedrooms
  • 3.5 Bathrooms
Corolla Wild Horse Tours

Corolla Wild Horse Tours knowledgeable guides will ensure you and your family have a great wild horse tour! Along the way the guides will stop and point out interesting sites and local history and details of the Corolla Wild Horses history. Be sure...

Lago Vista 77-K

Located in the popular beach community of Ocean Sands Section K, Lago Vista is the perfect backdrop for your Corolla beach vacation! A sparkling pool, relaxing hot tub and ample decking are just a few of the things that make the fabulous pool area...

  • Corolla
  • 5 Bedrooms
  • 4.5 Bathrooms
Miller's Waterfront Restaurant

MILLER’S OFFERS ONE OF THE FEW TRULY WATERFRONT DINING EXPERIENCES ON THE OUTER BANKS. Enjoy casual dining in our downstairs family-friendly seafood restaurant, or our signature drinks and grill menu in our upstairs deck bar while watching...

Stopp Inn & Relax CSC-3F

Stopp Inn and Relax is a beautifully furnished, 2 story, 3 bed/3 bath townhome with beautiful hardwood floors throughout the main living area, pristine carpet in the bedrooms, and partial ocean views. Stopp Inn and Relax is one of the units that...

  • Kill Devil Hills
  • 3 Bedrooms
  • 3 Bathrooms
5/31 - 6/7
$3,864  $4,364
$500 off
6/7 - 6/14
$4,326  $4,826
$500 off
6/14 - 6/21
$5,019  $5,519
$500 off
6/21 - 6/28
$5,404  $5,904
$500 off
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.