2026 Nags Head Sailing Tours Guide

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KEES Vacations

KEES Vacations offers the best Outer Banks rentals for family vacations, romantic weekend getaways and groups of all sizes looking for the perfect OBX rental for their stay. When booking with KEES Vacations, travelers can expect excellence in...

Siren Song

Located in Duck / 5 Bedrooms / 5 Full BathroomsAppreciate calming sunny days near the ocean in this roomy Sanderling home. Or appreciate the magnificent amenities this home has to offer! Including an exercise room with TV/DVD, treadmill and...

  • Duck
  • 5 Bedrooms
  • 5 Bathrooms
Paradise Dolphin Cruises

With the best views around and the quickest access to dolphins, Paradise Dolphin Cruises is committed to offering you one of the most amazing experiences of your life! Climb aboard the Kokomo, our 34-passenger catarmaran and the area’s newest...

ONE PARTICULAR HARBOUR

Relaxation is the sole purpose of “One Particular Harbour.” This beautiful, canalfront, one level ranch style rental cottage, located in the tree-lined Chicahauk area in the Town of Southern Shores, is perfect for peace and solitude. Enjoy...

  • Southern Shores
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
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...

1428 - Ocean Raves

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! NEW SUNDAY CHECK-IN FOR 2027! Ocean Raves is home to your next pet-friendly getaway on the picturesque shores of...

  • Corolla
  • 6 Bedrooms
  • 6.5 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...

1767 - Fox Snooze

Always Included, complimentary linens and made beds! New in 2024: Sunday Check-In.  If you're looking for an Outer Banks getaway, look no further than this 4 bedroom, 4.5 bathroom Corolla vacation...

  • Corolla
  • 4 Bedrooms
  • 4.5 Bathrooms
Super Wings

Best store on the beach! Everything you need for your vacation. Largest selection of beach supplies and the best deals on T-shirts, sweatshirts and mens, ladies, and kids, apparel, swimwear and resort wear. Get all your souvenirs, suntan lotions...

AV2-2B | Admirals View II Condo Unit 2B

This Exceptional Oceanfront Condo offers amazing views of the Atlantic. Step out onto the balcony & enjoy a cup of coffee while watching the dolphins play! With its modern décor & spacious floor plan this unit is the perfect fit. Centrally...

  • Kill Devil Hills
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
The Farmer's Daughter

Founded in 1984 on the coast of the Outer Banks, NC, Farmer’s Daughter still remains a destination for people wanting great quality, outstanding selection of unique clothing, accessories, and gifts at affordable prices. Committed to offering...

261 | The Beach House

This Nags Head Oceanfront home boasts outstanding Ocean Views & a spacious floor plan that includes 2 Oceanfront Private Suites, Hardwood Floors, Rec. Room w/Pool Table, Private 12x26 Swimming Pool, custom décor, & special touches...

  • Nags Head
  • 7 Bedrooms
  • 5.5 Bathrooms
  • Sleeps 16
Black Pelican

Black Pelican oceanfront restaurant is one of the Outer Banks’ premier restaurants serving lunch and dinner daily. Black Pelican is where you can enjoy fresh seafood, steaks, vegetarian dishes, sandwiches and some of the barrier island’s...

5435 - Carolina Gray

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Relax and unwind at Carolina Gray in Nags Head! This stunning Oceanside Outer Banks vacation home will impress from...

  • Nags Head
  • 5 Bedrooms
  • 5.5 Bathrooms
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.