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...

Sunny Daze 356-B

Enjoy the sounds of the sea and incredible ocean views just steps from the sand at Sunny Daze! With private beach access just outside your back door, you'll never want to stray far from this convenient vacation rental. A private oceanfront deck is...

  • Kill Devil Hills
  • 3 Bedrooms
  • 2.5 Bathrooms
Captain Johnny's Dolphin Tours

Join Captain Stuart Wescott aboard The Captain Johnny boat for a Guaranteed Dolphin Watch cruise in protected waters off the Outer Banks, NC. This two hour cruise is ideal for all ages. Enjoy breathtaking views as you listen to a...

PiraSea

Located in Corolla / 6 Bedrooms / 4 Full BathroomsThis handsome Oceanfront home features STRIKING OCEAN VIEWS from every room, decks galore, a private pool, hot tub, and direct beach access. With six well-appointed bedrooms and lighthouse vistas...

  • Corolla
  • 6 Bedrooms
  • 4 Bathrooms
Resort Realty Property Management

Celebrating 39 years of service in Outer Banks vacation rental property management, Resort Realty is a company that operates locally with in-house feet on the ground; meaning impeccable care for your home with constant communication from our staff...

ATOP IT ALL

RELAX...Head to ATOP IT ALL...Family-friendly home nestled high on a private, secluded lot, convenient access to ocean, sound and community playground. Enjoy the comforts of home in this 2,500 square foot cottage, private pool, and hot tub all to...

  • Southern Shores
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Risky Business Shrimping and Crabbing

If you’re looking for a fun, hands-on activity that the whole family can enjoy together, hop aboard Risky Business for an Outer Banks shrimping and crabbing charter. Our experienced captain and mate will show your group how to pull crab pots...

Tipsy Turtle

SEMI-OCEANFRONT Rodanthe - Hatteras Island Estates - At 6450 sq. ft. this striking 8 bedrooms and 7½ baths home has an elevator, exercise room, game room, a gourmet kitchen and handsome furnishing. TIPSY TURTLE will give you a grandiose Hatteras...

  • Rodanthe
  • 8 Bedrooms
  • 7.5 Bathrooms
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...

Dare Dreamer

OCEANFRONT Hatteras - Summerplace Dr. - Take a dip on the wild side in DARE DREAMER. Splash around in the pool while your family grilles up lunch under the pergola. Sit at the tiki bar in the pool area and make a fast drink to sip on as you watch...

  • Hatteras
  • 6 Bedrooms
  • 5.5 Bathrooms
Big Buck's Homemade Ice Cream

Serving our customers on the Outer Banks since 1994, Big Buck's ice Cream is dedicated serving you “The Best.” We offer a full line of super-premium ice cream products, smoothies, chocolates, and custom-made ice cream cakes! 2 locations...

1756 - Heavenly Shore

Always Included, complimentary linens and made beds! Enjoy a glorious beach getaway with your loved ones at this 5 bedroom, 3 bath vacation home that offers peaceful views of maritime woods and is...

  • Corolla
  • 5 Bedrooms
  • 5 Bathrooms
Old Man Charters

  Experience the Outer Banks from the water with Old Man Charters, a personalized boat tour company based in the historic fishing village of Wanchese. Departing from a private dock on the southern end of Roanoke Island, Old Man Charters...

5310 - Wright by the Beach

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! A pet-friendly OBX rental just 4 minutes from the beach? Yes, please! Wright by the Beach is a 5-bedroom, 3.5-bathroom...

  • Kill Devil Hills
  • 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.