2026 Nags Head 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...

PITTSPORT

4 bedrooms and large open living area with vaulted ceiling (all with ceiling fans and sliding glass doors opening to decks). 2200 plus square foot living area, plus over 1,300 square feet of sun and covered decks. 270 yards to beach access.Level...

  • Southern Shores
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Sleeps 9
The Christmas Shop

Discover gifts, garlands and glittering lights galore. Looking for a trinket for someone who has everything? Choose ornaments for every hobby, occupation, occasion or enthusiast; from the fisherman or Disney lover; dancer or photographer. Throughout...

Slam Dunk

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.Sound views are waiting for you and your family at this beautiful property in Monterey Shores. The expansive decks offer room for everyone to relax and...

  • Corolla
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 13
Corolla Raceway

The Ultimate Go Kart Racetrack That Kids and Adults will Enjoy! Corolla Raceway is the premier Go-Kart experience. Our upscale facility is designed to provide a first class entertainment experience. Corolla Raceway provides the newest Single...

028 | Fun Times

Outstanding location, Ocean Views, Private Swimming Pool, and Only 160 Ft. to Beach Access at Bittern St. are just part of what makes this terrific vacation home a wonderful choice for your stay on the Outer Banks. Fun Times is beautifully...

  • Nags Head
  • 4 Bedrooms
  • 4.5 Bathrooms
  • Sleeps 8
Outer Banks Blue

Since 2005, Outer Banks Blue has delivered exceptional vacations for OBX visitors. Our family-owned and locally managed rental company focuses on service and promises “a relaxing experience with a local touch.” Turn your dream vacation...

GREAT EXPECTATIONS

Overview Situated in a gated ocean-to-sound community, elevate your Outer Banks vacation to the next level by reserving Great Expectations. This sensational oceanfront estate features iconic ocean views, eight beautifully appointed...

  • Duck
  • 8 Bedrooms
  • 10 Bathrooms
Lost Treasure Golf

The noted explorer, archaeologist, anthropologist, paleontologist, and part-time plumbing contractor from the University of Chicago, Professor Duffer A. Hacker, led two expeditions to the outer banks in the late 1920’s. The purpose of these...

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
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...

817 | Hill Ocean 2

Hill Ocean II is a wonderful - Dog Friendly vacation home that is perfect for your next family vacation on the OBX. Located on a beautiful stretch of beach in Nags Head right on the Oceanfront, this 4 bedroom unit is a Private enough to be rented...

  • Nags Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
The Mystic Jewel

Walk into this shop and you’ll be delighted by all the glittering and sparkling from the way the mirrors and lighting show off jewelry from over 100 different designers and local artisans. Artfully-designed cases line the walls, filled with...

SUNSET

Enjoy spectacular views in an intimate community of Nags Head style townhomes. Each home features 2,000 square feet of living area.Level 1:Great room with sectional sofa, CATV and DVD player; partially covered deck with ocean view; kitchen; dining...

  • Southern Shores
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 7
5/2 - 5/9
$2,494  $2,861
$367 off
5/9 - 5/16
$2,494  $2,861
$367 off
5/23 - 5/30
$2,905  $3,329
$424 off
6/6 - 6/13
$4,323  $4,959
$636 off

Kitty Hawk Kites’ Whalebone Watersports Center is your one-stop shop for Outer Banks water adventures. Located on the Nags Head-Manteo Causeway right on Roanoke Sound, this location offers it all – dolphin watching cruises with a marine...