2026 Nags Head Sailing Tours Guide

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Miss Oregon Inlet

Oregon Inlet Fishing Center is the home of the largest and most modern charter boat fishing fleet on the eastern seaboard. A full service marina in Nags Head NC, Oregon Inlet offers a comprehensive charter boat fishing experience for the "old salt...

Catchin Waves

Located in Corolla/ 4 Bedrooms/ 3 Full Bathrooms/ 1 Half BathCatchin Waves is centrally located in the heart of Corolla! This Friday to Friday rental is a bright and comfortable home with 4 bedrooms 3.5 baths and 2 living spaces with plenty of...

  • Corolla
  • 4 Bedrooms
  • 3 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...

The Tui 459-D

This beach home has everything your family needs for a wonderful Outer Banks vacation. The top level features a huge great room with flat screen TV and ocean views, a well-stocked kitchen with bar seating and a dining table. Relax in the private...

  • Nags Head
  • 6 Bedrooms
  • 5.5 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...

PIRATES ESCAPE

Eight bedroom suites, each with its own private bath, set Pirates Escape apart among oceanfront Nags Head homes from Carolina Designs. A media lounge with custom tiered seating, a rec room, and an elevator make this Milepost 16 oceanfront...

  • Nags Head
  • 8 Bedrooms
  • 10 Bathrooms
Cosmo's Pizzeria Southern Shores

If you're searching for great pizza on the Outer Banks, look no further than Cosmo's Pizzeria at The Marketplace in Southern Shores! We offer authentic New York-style pizza made fresh and just the way you like, using only the highest quality...

074 | Keefe's Castle

Oceanfront-South Nags Head-Dog FreindlyA wide, spacious Beach & terrific Ocean Views await when you choose Keefe's Castle for your Outer Banks vacation. Nothing can be finer than watching the sunrise over the beautiful, blue Atlantic Ocean...

  • Nags Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Corolla Wild Horse Tours

Corolla Wild Horse Tours knowledgeable guides will ensure you and your family have a great wild horse tour! Along the way the guides will stop and point out interesting sites and local history and details of the Corolla Wild Horses history. Be sure...

875 | Yellow Bird

Enjoy beautiful Ocean and Beach Views right from your deck! Yellow Bird is a terrific Kill Devil Hills beach cottage that features bright décor, comfortable furnishings, and steps that lead right down to the Beach. This very nice home that is...

  • Kill Devil Hills
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 8
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...

Carolina Breeze 235-A

Just a short walk to the beach, Carolina Breeze is a lovely 4 bedroom 2 bath oceanside beach cottage in Kitty Hawk. Located on a small side street, Carolina Breeze is in a great location with access to the beach within a few hundred feet. You will...

  • Kitty Hawk
  • 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...

Surf's Up

OCEANFRONT Frisco - Sandpiper Dr. - SURF'S UP at this statuesque oceanfront beach escape with unique floorplan. A line-up of oceanfront bedrooms await most members of your event along with multiple gathering and entertainment options. Begin on the...

  • Frisco
  • 7 Bedrooms
  • 7.5 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.