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...

Our Perfect View 203-A

Wake up to the sounds of the waves crashing at Our Perfect View, a quaint, 4 bedroom oceanfront cottage in the heart of Kitty Hawk at milepost 3.5. The winding dunes and blue waters just outside create a picturesque scene you won’t soon forget...

  • Kitty Hawk
  • 4 Bedrooms
  • 1 Bathrooms
6/27 - 7/4
$4,091  $5,091
$1,000 off
Cosmo's Pizzeria Southern Shores

If you're searching for great pizza on the Outer Banks, look no further than Cosmo's Pizzeria at The Marketplace in Southern Shores! We offer authentic New York-style pizza made fresh and just the way you like, using only the highest quality...

Lighthouse 494-A

Aptly named Lighthouse, this 7 bedroom, 6 1/2 bath semi-oceanfront home at milepost 15 in the heart of Nags Head is signaling to your family that you have found the perfect spot for your next Outer Banks vacation. Lounge beside the private pool...

  • Nags Head
  • 7 Bedrooms
  • 6.5 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...

5379 - Big Eyed Fish

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! A whimsical, tropical getaway awaits you at Big Eyed Fish, located on the beautiful Oceanfront of Kill Devil Hills...

  • Kill Devil Hills
  • 2 Bedrooms
  • 2 Bathrooms
Nags Head Dolphin Watch

Scientists run these dolphin tours as part of their research on these beloved aquatic animals, so you know this will be an interesting trip. Passengers will be able to see how researchers with the Outer Banks Center for Dolphin Research, a nonprofit...

BLUE MARLIN I

Relax and enjoy the beautiful, panoramic ocean views from this oceanfront home located in Southern Shores, approximately a half of a mile from Croatan Highway (bypass road) with easy in-and-out access. This wonderful home offers everything you and...

  • Southern Shores
  • 6 Bedrooms
  • 6.5 Bathrooms
  • Sleeps 14
6/27 - 7/4
$8,506  $13,632
$5,126 off
8/15 - 8/22
$8,774  $11,096
$2,322 off
8/29 - 9/5
$7,026  $8,561
$1,535 off
9/5 - 9/12
$6,441  $7,836
$1,395 off
9/19 - 9/26
$6,182  $7,021
$839 off
9/26 - 10/3
$6,042  $7,021
$979 off
10/3 - 10/10
$6,042  $7,021
$979 off
10/10 - 10/17
$6,042  $7,021
$979 off
10/24 - 10/31
$5,064  $5,572
$508 off
10/31 - 11/7
$5,064  $5,421
$357 off
11/7 - 11/14
$4,914  $5,421
$507 off
11/14 - 11/21
$4,914  $5,421
$507 off
11/21 - 11/28
$4,914  $5,421
$507 off
11/28 - 12/5
$4,914  $5,421
$507 off
12/5 - 12/12
$4,914  $5,421
$507 off
12/12 - 12/19
$4,914  $5,421
$507 off
12/19 - 12/26
$5,349  $5,421
$72 off
12/26 - 1/2
$5,234  $5,421
$187 off
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...

Lemonade

SEMI-OCEANFRONT Salvo — Ocean St. — Fun fact: just a whiff of lemon can boost your mood and reduce anxiety. Maybe that’s why sipping a thirst-quenching, cool glass of lemonade evokes all those laid-back feels of a carefree hideaway. Loaded...

  • Salvo
  • 8 Bedrooms
  • 8.5 Bathrooms
Southern Shores Realty

Southern Shores Realty offers over 350 Outer Banks rentals from Corolla to S. Nags Head.  We've been an Outer Banks tradition since 1947, providing families just like yours with memories that last a lifetime.  Take a moment to search...

244 | The Teal Turtle

6/16/26: Beach Nourishment has been completed in this area. Come and enjoy the refreshed beach! Oceanside-South Nags Head. A Terrific Location, Ocean views, spacious interior are just part of what makes "The Teal Turtle" a great choice for your...

  • Nags Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
7/5 - 7/11
$3,295  $3,895
$600 off
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...

Southern Paws

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.Take a break at “Southern Paws” with your family! Outstanding lakeside property and only a short walk to the beach! Enjoy the beautiful kitchen...

  • Corolla
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 14

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...