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...

SEA WINDS

Six bedrooms, each with a private bathroom and five of them with king beds, set Sea Winds apart among Carolina Designs vacation rentals in Kill Devil Hills. This semi-oceanfront home at Milepost 6.5 pairs that rare bedroom lineup with a 32 x 16...

  • Kill Devil Hills
  • 6 Bedrooms
  • 7 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...

Island Fantasy

SOUNDSIDE Salvo - Sand Dollar Ct. - Start your ISLAND FANTASY soaking in the rays by your shining private swimming pool and enormous 8-person hot tub with convenient cabana bath. Step inside and appreciate the game room with pool table and wet bar...

  • Salvo
  • 7 Bedrooms
  • 8.5 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...

889 | Sandpiper's Run

Sandpiper's Run is a lovely Kitty Hawk vacation home that provides everything for your family to enjoy. Located only two lots back from the ocean with easy access to the beach (approximately 250 yards to Beach Access at E. Eckner Street) this is...

  • Kitty Hawk
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Sleeps 10
Brindley Beach Vacations

Brindley Beach Vacations offers premier Real Estate and Property Management services across the entire Outer Banks. Representing more than 450 vacation rental homes, we proudly serve every region—from the southern beaches of Hatteras Island...

SEAS THE DAY

“SEAS THE DAY” is centrally located in the heart of Duck with convenient access to the beach, sound, shops, restaurants, the Duck Town Park with open lawn space, and the sound front boardwalk to catch the breathtaking sunsets! You can park your...

  • Duck
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 8
11/7 - 11/14
$1,699  $1,750
$51 off
11/14 - 11/21
$1,717  $1,750
$33 off
11/28 - 12/5
$1,735  $1,750
$15 off
12/5 - 12/12
$1,699  $1,750
$51 off
12/12 - 12/19
$1,717  $1,750
$33 off
Kitty Hawk Kites

Looking to fly a kite on the beach or atop the spectacular dunes of Jockey’s Ridge State Park? Kitty Hawk Kites offers the largest selection of kites, wind art, flags, games, and toys on the Outer Banks, with experts on staff to get you flying...

Elysian Sands S-250

Elysian Sands is paradise found. Derived from Elysium in post-classical literature, meaning paradise, this beautiful vacation home holds true to its roots. The panoramic ocean views from the top level will take your breath away. Comfortable seating...

  • Salvo
  • 4 Bedrooms
  • 2.5 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...

True at First Light

Located in Duck / 9 Bedrooms / 9 Full Bathrooms / 1 Half BathroomPrepare to indulge in the ultimate Outer Banks hideaway at this pretty, oceanfront Brindley Beach Vacations home. With its thoughtful design and an astonishing array of opulent...

  • Duck
  • 9 Bedrooms
  • 9 Bathrooms
Corolla Wild Horse Fund

We are The Corolla Wild Horse Fund the non-profit 501 (c) (3) charity responsible for the care and protection of the wild Banker horses roaming the northernmost beaches of the Outer Banks. Join us in the summer season, every Wednesday morning from...

K8003 SOCO Oceanfront Luxury

Welcome to SOCO by KEES Vacations! SOCO in Nags Head is a stunningly beautiful and unique vacation property with dark wood floors, whitewashed walls and exposed beam ceilings. Built in 2015, SOCO has every modern amenity. In the backyard, there is...

  • Nags Head
  • 8 Bedrooms
  • 11 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.