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...

Outside-In

Indulge in an unparalleled vacation experience at Outside-In, a magnificent waterfront estate nestled in the picturesque setting of Nags Head. This exquisite retreat offers direct access to the pristine shores of the ocean, inviting you to immerse...

  • Nags Head
  • 8 Bedrooms
  • 8 Bathrooms
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...

Don't Worry Beach Happy 479

Unwind, relax and get in the island frame of mind at Don’t Worry Beach Happy, a spectacular 8 bedroom, 8 and 3 half bath semi-oceanfront stunner in the heart of Nags Head. Designed, decorated, and outfitted with the singular goal of providing...

  • Nags Head
  • 8 Bedrooms
  • 9.5 Bathrooms
Brew Thru

No trip to the Outer Banks is complete without cruising through Brew Thru, the Outer Banks’ original drive thru convenience store. Whether you’re looking for a refreshing cold beverage of Coke, Pepsi and other soft drinks on the go...

La Maison de la Mer

Located in Corolla in the private neighborhood of Ocean Sands section F/ Dog Friendly/ 6 Bedrooms / 4 Full Bathrooms / 2 Half BathroomsCavernous Outer Banks coastal getaway, well-appointed and thoughtfully designed, less than a 5-min. walk to the...

  • Corolla
  • 6 Bedrooms
  • 4 Bathrooms
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...

Mermaid's Lair

Mermaid’s Lair is a great value for families that love the beach! Private pool has lots of room for the kids to play around the pool while adults soak up the sun. Best features are the view, decks and that great dune top deck. . .it’s huge...

  • Nags Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
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...

7011 - Banzai Landing

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! New for 2026: New TVs in the Master Bedroom, Living Room, Bunk Room, and a Massive New 65 Inch in the Game room, All...

  • Rodanthe
  • 6 Bedrooms
  • 6.5 Bathrooms
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...

Stella Maris A-36

Welcome to Stella Maris! This gorgeous, bright and airy, newly-constructed home was designed and furnished to ensure you have the perfect Outer Banks vacation experience! Located just a short walk to the beach (approximately 0.2 miles), and close to...

  • Avon
  • 3 Bedrooms
  • 2 Bathrooms
Carolina Designs Realty

Plan your Outer Banks vacation with Carolina Designs! Browse our inventory of 350+ select Outer Banks vacation rentals located in the towns of Corolla, Duck, Southern Shores, Kitty Hawk, Kill Devil Hills, and Nags Head. Book online anytime, or reach...

Rum Runner

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.Almost Oceanfront (475 feet to the beach), this MAGNIFICENT 10 bedroom with 42” Smart TVs, 10 full baths, 2 half bath beach home is spectacular from...

  • Southern Shores
  • 10 Bedrooms
  • 10 Bathrooms
  • Sleeps 21
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.