2026 Nags Head Sailing Tours Guide

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Fish Heads Bar and Grill

Rustic waterfront pub at a fishing pier with a large deck for seafood eats, draft beer & live music. Fish Heads Bar and Grill is THE tiki bar of the Outer Banks. Located at Mile Post 18.5 in Nags Head, we offer a view that is second to none...

Suit's Us 61-E

Located in the Ocean Sands community, Suit's Us is a beautiful home loaded with amenities and less than 2 minute walk to the ocean, 2 minute drive to Currituck Club Premier Golf, and Harris Teeter grocery store. Enjoy beautiful views of sunsets from...

  • Corolla
  • 5 Bedrooms
  • 3 Bathrooms
Surf or Sound Realty

Surf or Sound Realty invites you to explore our collection of over 600 premier vacation rental homes on Hatteras Island, featuring the largest selection of oceanfront accommodations. Nestled within the breathtaking Cape Hatteras National Seashore...

1366 - Whale Spray

Always Included, complimentary linens and made beds! THIS IS A PET FREE HOME. Whale Spray is a uniquely designed oceanfront rental home ready for your Outer Banks vacation! Located in Corolla, Whale...

  • Corolla
  • 5 Bedrooms
  • 5 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...

Sun Byrne

This charming classic Nags Head beach cottage captures the essence of a true Outer Banks getaway. Ideally situated just three houses from the shore, you’ll enjoy effortless access to the wide, sandy beaches of South Nags Head—no streets to...

  • Nags Head
  • 3 Bedrooms
  • 1 Bathrooms
Duck Corolla Parasail

Discover the beauty of the Outer Banks with Duck Parasail. Duck Parasail is proud to partner with Corolla Parasail and together, they take pride in being the longest running, family owned and operated parasail company on the Outer Banks. Duck...

Starfish Cottage 122-D

Just steps away from the beach access, enjoy the sound of the ocean and salt-kissed breezes at Starfish Cottage!. Relax in the hammock with a book and your daydreams, or on the wraparound deck at this classic Carolina beach cottage in Duck.Feel...

  • Duck
  • 4 Bedrooms
  • 2 Bathrooms
TRiO Restaurant & Market

Wine, beer and cheese lovers will love TRiO, an exciting retail and tasting destination in Kitty Hawk. Both a gourmet retail wine, beer and cheese shop as well as a bistro with a wine bar and tap house, TRiO offers the best of the worlds of...

859 | Mt. Hope South

Updates completed for the 2026 season include New Living Room Furnishings, New Flooring in Living Areas, and Freshly Painted Interior and Exterior! This cozy Outer Banks cottage offers an ideal location that affords easy access the Beach...

  • Nags Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
8/8 - 8/14
$1,995  $2,195
$200 off
8/15 - 8/21
$1,795  $1,995
$200 off
8/22 - 8/28
$1,595  $1,795
$200 off
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...

Pier House

Located in Rodanthe | 3 Bedrooms | 2 Full BathroomsWelcome to Pier House!  Ideal for modest groups, this cute oceanfront bungalow provides striking ocean vistas from inside and outside, with nothing between you and the beach but a sand dune. You...

  • Rodanthe
  • 3 Bedrooms
  • 2 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...

Koo Koo's Nest

Just a few steps from the ocean, this well equipped and comfortably appointed house, has the makings for a perfect vacation. Enjoy the wonderful ocean view from the front and back decks, as well as the screened in porch. Relax by the 12’ X 26’...

  • Corolla
  • 4 Bedrooms
  • 2 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.