2026 Sailing Tours Guide

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Jumpmasters OBX

Now with Axe Throwing! Jumpmasters OBX is the ultimate trampoline park on the Outer Banks with attractions the entire family will enjoy. From open jump trampolines to the dodgeball court, 3-D climbing wall, a foam pit, an epic ninja obstacle course...

5784 - Emerald

Always Included, complimentary linens and made beds! Emerald is oceanfront in South Nags Head nestled between Jennette’s Pier and Outer Banks Pier in a quiet area. Close to great local OBX...

  • Nags Head
  • 5 Bedrooms
  • 5 Bathrooms
American Pie

Discover the best homemade ice cream and authentic made-from-scratch New York Style pizza the Outer Banks has to offer at American Pie in Kill Devil Hills. An Outer Banks favorite for lunch, dinner or a delicious scoop of scrumptious ice cream after...

Into the Mystic

OCEANSIDE Avon – Sailfish Lane – Smell the sea and feel the sky, indeed, when you settle INTO THE MYSTIC, a three-bedroom/three-bath home located just steps from the sandy Atlantic shore. Freshly refreshed and soothingly calm, this home is the...

  • Avon
  • 3 Bedrooms
  • 3 Bathrooms
Gray's

Gray’s Outer Banks Lifestyle Clothing Company offers the absolute best in Outer Banks T-shirts and Sweatshirts including Champion, Under Armour with "Outer Banks” and Gear! We carry quality fashions and accessories for the whole family...

5701 - Coral Castle

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Coral Castle is the Nags Head vacation rental you've been searching for! This 5 bedroom, 5.5 bathroom Outer Banks...

  • Nags Head
  • 5 Bedrooms
  • 5.5 Bathrooms
Paradise Fun Park

Off the beach, one of the best activities for groups to enjoy in the Outer Banks is mini golf, bumper cars or Go-Karts. Thankfully, Paradise Fun Park offers all three activities! Paradise Fun Park offers exciting outdoor activities that kids and...

6334 - Hope and Dreams

Always Included, complimentary linens and made beds! An ideal getaway for your family to enjoy fantastic ocean views and the tranquility found in South Nags Head. Hope and Dreams is nicely located...

  • Nags Head
  • 4 Bedrooms
  • 4 Bathrooms
Awful Arthur's Oyster Bar

Welcome to the home of the happy oyster where for over 40 years the oyster has been our world. The Outer Banks only authentic oyster bar is the place to enjoy sensational fare from the sea washed down with your favorite brew or cocktail. We serve by...

Gray Man's Dune 123-A

Ready for a classic Outer Banks vacation? Gray Man’s Dune is a spacious oceanfront home positioned in the perfect spot for your family to relax, unwind, and play! Enjoy the oceanfront bubbling hot tub, WiFi, and close proximity to shopping...

  • Duck
  • 4 Bedrooms
  • 3 Bathrooms
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...

Summerwind

Located in Corolla / 7 Bedrooms / 6 Full Bathrooms / 2 Half BathroomsThis opulent oceanfront home sits on a high elevation offering gorgeous ocean vistas. Of particular note, the design of Summerwind provides wide-span Ocean and beach vistas from...

  • Corolla
  • 7 Bedrooms
  • 6 Bathrooms
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...

Arcadia

Located at the end of a cul-de-sac, this semi-oceanfront home boasts peaceful ocean views from the oceanside deck and is a short car/bike ride run/walk to the Town of Duck and local attractions like North Duck Water Sports, and Sanderling resort...

  • Duck
  • 4 Bedrooms
  • 2 Bathrooms

Corolla Water Sports is the original, most comprehensive, and best water sports location on the Northern Outer Banks. We have been providing a first class facility for many years, and have had thousands of happy customers over this time. We are...

Sail local waters in a handsome schooner with plenty of elbow room.

You can truly choose your own Outer Banks adventure with this company that has a mission to promote conservation and respect for the natural resources of the OBX while creating fun and family-friendly experiences that highlight the beauty of this...

A beautiful and recreational stop for watersport fun. 

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...

Looking for a private sail charter? Call the folks at Sail Outer Banks. They offer a variety of year-round trips with low minimum fees to make it within reach of many folk. Dan and Katherine are your crew. Dan is a licensed U.S. Coast Guard captain...

Sail the Outer Banks (formerly Outer Banks Sailing Academy) offers professional sailing instruction operating under the standards of the American Sailing Association. They offer lessons in Kill Devil Hills. The Academy presents an array of classes...