2026 Nags Head Sailing Tours Guide

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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...

191 | White Marlin

Endless ocean views, comfortable furnishings & bright decor make White Marlin a terrific choice for your Outer Banks vacation. Situated on the oceanfront at milepost 16 in Nags Head, this home provides the luxury of having your own Private...

  • Nags Head
  • 8 Bedrooms
  • 7.5 Bathrooms
  • Sleeps 16
5/16 - 5/22
$4,595  $5,495
$900 off
5/23 - 5/29
$5,895  $6,795
$900 off
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...

1530 - Summer Moon

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Luxury amenities and the most perfect Outer Banks vacation await you at Summer Moon! Summer Moon is a 6 bedroom 5.5...

  • Corolla
  • 6 Bedrooms
  • 6 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...

K9031 Wicked Fun at Windswept Ridge

Welcome to Wicked Fun at Windswept Ridge Golf Villas! You will love this first-level, one-floor living space. It's a perfect Corolla beach vacation rental. There's a little something for everyone at Wicked Fun. This is a property nestled in the...

  • Corolla
  • 3 Bedrooms
  • 3 Bathrooms
Miller's Seafood and Steakhouse

Miller's Seafood & Steakhouse has been a favorite among locals and visitors for more forty years. Offering delicious southern cuisine for both breakfast and dinner in a casual family atmosphere infused with coastal flair, it's no wonder this...

5441 - Rascoe

Always Included, complimentary linens and made beds! This "Old Nags Head" style Cottage, built in 1931, should be on an Historic Register! This antique home has been preserved with the utmost care...

  • Nags Head
  • 5 Bedrooms
  • 5.5 Bathrooms
The Cotton Gin

For those traveling to the Outer Banks, The Cotton Gin is a beloved landmark with its large windmill and picturesque gardens. The Cotton Gin has stood in the same location since 1929, starting as a working cotton gin and growing to a gift store with...

Against All Odds

Welcome to your Outer Banks getaway! This 4-bedroom, 2-bath retreat in the Sea Hawk community offers the perfect blend of comfort and convenience plus, it's dog-friendly, so your four-legged family members can join in on the fun. From the home, hop...

  • Duck
  • 4 Bedrooms
  • 2 Bathrooms
Sound Feet Shoes

Sound Feet Shoes is family owned and operated. Sound Feet has been in the retail shoe business for over 72 years, opening their first store in 1953. They provide the best customer service and are the only Outer Banks’ area full service shoe...

TIDES THAT BIND

Overview Decks, decks, and more decks! If you enjoy spending time outside to bask in the sunshine, breathe in the fresh coastal air, enjoy an elevated view of the horizon, and let any worry on your mind float away, Tides That Bind is...

  • Corolla
  • 8 Bedrooms
  • 7 Bathrooms
ZoomAround Street Legal Golf Cart Rentals

ZoomAround Street Legal Golf Cart Rentals provides our communities and our visitors with fun, safe and convenient access to innovative transportation while providing an unparalleled customer experience. Don’t carry all of your beach gear...

7594 - The Hatch

Always Included, complimentary linens and made beds! New for 2026: New Flooring, Updated Kitchen, Updated Bathrooms, New Adirondack Deck Chairs. Welcome to The Hatch, a beautifully appointed...

  • Avon
  • 3 Bedrooms
  • 3 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.