2026 Nags Head Sailing Guide

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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...

Anna

ANNA is a wonderful place to relax and enjoy your vacation. If you don’t want or need a McMansion for your group, ANNA could be just what you are looking for. She is the perfect size for couples and family gatherings up to 10 people. The property...

  • Corolla
  • 4 Bedrooms
  • 2 Bathrooms
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...

5215 - Dolphin Dreaming

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Ultimate relaxation will be yours at this Oceanfront condo located in The Golden Strand complex in Kill Devil Hills...

  • Kill Devil Hills
  • 3 Bedrooms
  • 3 Bathrooms
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...

247 | Ahhh...Notta Worry

"Ahhh…Notta Worry" is a terrific family vacation destination that is nicely decorated & very comfortable, this home is situated directly across the beach road from the ocean & only 150 Ft. from Second Street Beach Access. Very close to...

  • Kill Devil Hills
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
The Mystic Jewel

Walk into this shop and you’ll be delighted by all the glittering and sparkling from the way the mirrors and lighting show off jewelry from over 100 different designers and local artisans. Artfully-designed cases line the walls, filled with...

STAIRWAY TO HEAVEN

Overview If your idea of heaven is vacationing in a harmonious beach retreat with tasteful upgrades, stylish cottage decor and show stopper ocean views, elevate your next Outer Banks getaway by reserving Stairway To Heaven. Spend your...

  • Duck
  • 5 Bedrooms
  • 6.5 Bathrooms
Sun Realty

Sun Realty offers the Best Selection of Vacation Rentals on the Outer Banks. Our large selection of Outer Banks rentals means you can choose from a wide range of amenities, including private swimming pools, hot tubs, theater rooms, game rooms, pet...

7227 - Point Break 919

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! A semi-oceanfront Hatteras Island retreat is found right here; welcome to Point Break 919! Located in Salvo on...

  • Salvo
  • 4 Bedrooms
  • 4 Bathrooms
OBX Laser Tag and Arcade

Here’s some high energy entertainment for the kids, and for young adults (or young at heart) who love laser tag. On one side of this large facility is the “moon bounce inflatable room,” where the young ‘uns can go and bounce...

GRAND VIEW

Spectacular location on a high dune with panoramic views of ocean and sound - just three lots from oceanfront and beach access. Relax in the 14 x 28 pool and hot tub for 6. Every room has view of ocean or sound. Enjoy beautiful sunrises and sunsets...

  • Duck
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
6/27 - 7/4
$4,042  $5,220
$1,178 off
7/4 - 7/11
$4,110  $5,220
$1,110 off
7/11 - 7/18
$4,278  $5,220
$942 off
8/22 - 8/29
$3,392  $3,590
$198 off
8/29 - 9/5
$2,793  $3,046
$253 off
9/5 - 9/12
$2,436  $2,684
$248 off
9/12 - 9/19
$2,050  $2,231
$181 off
9/19 - 9/26
$2,039  $2,231
$192 off
9/26 - 10/3
$1,887  $2,050
$163 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...

833 | Entropy

Lovely décor, comfortable furnishings and a great location that is within easy walking distance of the Beach make Entropy an excellent choice for your family retreat to the Outer Banks. Only three lots back from the beach w/direct access and...

  • Nags Head
  • 6 Bedrooms
  • 4.5 Bathrooms
  • Sleeps 15
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.