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...

7564 - Stargazer

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Nestled just steps from the beach, Stargazer is a nearly ocean-front haven perfect for your next Hatteras Island...

  • Avon
  • 4 Bedrooms
  • 4 Bathrooms
Wild Horse Adventure Tours

Wild Horse Adventure Tours has been voted the #1 tour company in the USA by TripAdvisor. Feel the ocean breeze and taste the salty beach air as you cruise the Outer Banks beaches in our exclusive OPEN AIR, 13-passenger Hummers with one of...

DOLPHIN WATCH

Ahoy me hearties, hoist the mainsail and set course for “Dolphin Watch” , a brand new haven where pirates and Commodores can parlay and parlee, over a glass of grog.Swashbuckling fun and naval history take us back to a time when The Black Pearl...

  • Southern Shores
  • 5 Bedrooms
  • 5.5 Bathrooms
  • Sleeps 14
6/5 - 6/12
$9,001  $9,961
$960 off
6/12 - 6/19
$9,771  $10,504
$733 off
6/26 - 7/3
$10,790  $11,606
$816 off
7/3 - 7/10
$11,449  $11,606
$157 off
Just for the Beach Rentals

Just for the Beach Rentals (not to be confused with the similarly-named "Just for the Beach") offers rentals to accommodate your stay. Equipment includes linens, baby gates, cribs, monitors, seats, joggers, bikes, kayaks, skim boards, surf boards...

Woodhaven

Located in Corolla/ 4 Bedrooms/ 4 Full BathroomsA coastal bungalow at its best! Great ocean vistas from the bright and open great room, sun room or decks. Fantastic home office space.  Only 6 tons from the wide and private beaches of Ocean Sands...

  • Corolla
  • 4 Bedrooms
  • 4 Bathrooms
Coastal Smoothie Cafe

At Coastal Smoothie Cafe, we have created a menu and atmosphere that is designed to be as unique as the northern shores of the Outer Banks. Our creations utilize fresh local produce when possible. There is nothing better than local NC strawberries...

OC1 The Docker's Cottage at Oceanside Co...

Welcome to The Docker's Cottage at Oceanside Court by KEES Vacations! These quaint oceanfront cottages are the perfect place for you and your family to have a unique and unforgettable vacation offering the perfect balance between amenities and...

  • Nags Head
  • 1 Bedrooms
  • 1 Bathrooms
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...

Two Cay Seas

OCEANFRONT Avon- Gull's Cry Rd. Located on a peaceful cul-de-sac in Avon, this home with direct beach access offers some of the best ocean vistas to be found. The first level has four bedrooms with oceanfront deck off two bedrooms, two baths, and...

  • Avon
  • 4 Bedrooms
  • 2.5 Bathrooms
Miller's Seafood and Steakhouse

Miller's Seafood & Steakhouse has been a favorite among locals and visitors for more forty years. Offering delicious southern cuisine for both breakfast and dinner in a casual family atmosphere infused with coastal flair, it's no wonder this...

Livin The Dream

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.Fabulous ocean views set the pace for Livin the Dream, this gorgeous semi-oceanfront property in South Nags Head. Just across the street from the beach...

  • Nags Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 9
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...

THREE LITTLE BIRDS

You won't have to worry about a thing, when you stay at the "Three Little Birds" cottage. This 4 bedroom, 3 bath oceanside home is a short walk to your own public beach access which is only 275 yards away on a very private street. When you are ready...

  • Southern Shores
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
5/1 - 5/8
$2,155  $2,360
$205 off
5/8 - 5/15
$2,073  $2,360
$287 off
6/5 - 6/12
$3,838  $4,103
$265 off
8/21 - 8/28
$3,200  $3,400
$200 off
9/11 - 9/18
$2,286  $2,491
$205 off
9/25 - 10/2
$2,169  $2,360
$191 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...