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...

The Porch Life

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.Welcome to The Porch Life — a no-fuss, no-frills family beach house that’s all about comfort, connection, and location. Perched right on the...

  • Nags Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
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...

HAKUNA MATATA

Enjoy a "NO WORRY" vacation in a private, treed setting. Pleasant 455-yard walk to beach access.Level 1:Powder room.Level 2:North side - 2 bedrooms (1 with Queen, CATV: opening to deck with swing and overlooking pool, connecting bath (with tub and...

  • Southern Shores
  • 5 Bedrooms
  • 3.5 Bathrooms
  • Sleeps 10
5/22 - 5/29
$2,042  $2,122
$80 off
6/26 - 7/3
$3,697  $4,049
$352 off
7/17 - 7/24
$3,848  $4,049
$201 off
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...

Heezen HOB-5816

Looking for a spacious vacation home that’s pet friendly, offers a panoramic view of the ocean, and has private beach access? Then breeze into Heezen today! Located in South Nags Head, this oceanfront property offers peace and quiet from the noisy...

  • Nags Head
  • 5 Bedrooms
  • 3.5 Bathrooms
H2OBX Waterpark

YOUR BEST SUMMER DAY - Nothing satisfies your craving for fun like a day at the H2OBX Waterpark. Start with that perfect Carolina sun. Add a dose of adrenaline as you soar 6 stories up on The Rogue Wave or drop 90 screaming feet down The Plank...

Kings Landing

Located in Corolla / 10 Bedrooms / 9 Full Bathrooms / 2 Half BathroomsFeel unparalleled luxury at the palace on the sea…. King’s Landing! Oceanfront living is at its best at this freshly modernized Buck Island home. King’s Landing is the ideal...

  • Corolla
  • 10 Bedrooms
  • 9 Bathrooms
Henry's Restaurant

Henry's Restaurant offers down home, simple food done Outer Banks style. Henry's Restaurant has been serving the Outer Banks of North Carolina since the summer of 1989. They are pleased to be considered one of the most popular restaurants in Dare...

OCEAN SOL

Carolina Designs presents OCEAN SOL, an extraordinary 15-bedroom Corolla retreat that redefines luxury OBX vacationing. This one-of-a-kind Whalehead estate features 15 private baths, a wine room, home theater, sauna, and 32x16 private pool with hot...

  • Corolla
  • 15 Bedrooms
  • 16 Bathrooms
Wanchese Marina

Wanchese Marina offer one of the finest fleets of professional charter fishermen, charter booking service, dolphin tours, dive charters, shrimp charters and even crabbing charters. We have both diesel and non-ethanol fuel, a professional fish...

PELICANS NEST

Enjoy spectacular views in an intimate community of Nags Head style townhouses. Each home features 2,000 square feet of living area.10 yards to beach access. Pelican Watch complex has great beach access and is next door to the Kitty Hawk Pier and...

  • Southern Shores
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 7
5/30 - 6/6
$3,935  $4,342
$407 off
6/6 - 6/13
$4,210  $4,617
$407 off
6/20 - 6/27
$4,940  $5,429
$489 off
7/4 - 7/11
$5,429  $5,972
$543 off
Wild Horse Adventure Tours

Wild Horse Adventure Tours has been voted the #1 tour company in the USA by TripAdvisor. Feel the ocean breeze and taste the salty beach air as you cruise the Outer Banks beaches in our exclusive OPEN AIR, 13-passenger Hummers with one of...

5418 - Family Tides

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds!If you're looking for a spacious and accommodating Outer Banks rental home, look no further than Family Tides! This...

  • Nags Head
  • 10 Bedrooms
  • 10 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.