2026 Nags Head Sailing Tours Guide

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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...

Blue Crush

Come and experience the beautiful Atlantic Ocean, only steps from your back door! If you want the best of everything, Blue Crush is it! Location, Amenities, Master Bedrooms, and Pet-Friendly - then this is your rental!  You will enjoy hours of...

  • Kill Devil Hills
  • 10 Bedrooms
  • 11 Bathrooms
Risky Business Shrimping and Crabbing

If you’re looking for a fun, hands-on activity that the whole family can enjoy together, hop aboard Risky Business for an Outer Banks shrimping and crabbing charter. Our experienced captain and mate will show your group how to pull crab pots...

Whisper of the Waves WHL-30

Just 340 feet from the sand and surf, Whisper of the Waves is the perfect semi-oceanfront escape for your next Outer Banks vacation. With 7 bedrooms, a private pool, hot tub, and plenty of space for the whole family - including your dog - this...

  • Corolla
  • 7 Bedrooms
  • 3.5 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...

Sunshine & Tan Lines

Located in Corolla / 3 Bedrooms / 3 Full Bathrooms / 1 Half BathroomYour family will adore this vacation home located in the award-winning resort community of Corolla Light. Located just across the street from the newly modernized indoor pool and...

  • Corolla
  • 3 Bedrooms
  • 3 Bathrooms
Nor'Banks Sailing & Watersports

Nor'Banks Sailing & Watersports beautiful location and top-of-the-line equipment, together with a friendly and professional staff make it one of the premier water sports centers on the Outer Banks. Nor'Banks' sound front location has a huge...

Brass Ring

NEW TO BRINDLEY BEACH FOR 2026!Located in Corolla / 5 Bedrooms / 2 Full BathroomsWelcome to Brass Ring located in Caffey's Inlet in the heart of Duck. This home, located on a private cul-de-sac, is the ideal getaway for family and...

  • Duck
  • 5 Bedrooms
  • 2 Bathrooms
7/11 - 7/18
$2,736  $3,290
$554 off
7/17 - 7/24
$2,803  $3,374
$571 off
7/23 - 7/30
$2,803  $3,374
$571 off
7/30 - 8/6
$2,803  $3,374
$571 off
9/2 - 9/9
$2,355  $2,814
$459 off
9/8 - 9/15
$2,405  $2,615
$210 off
9/13 - 9/20
$2,031  $2,199
$168 off
9/15 - 9/22
$2,031  $2,199
$168 off
9/16 - 9/23
$2,184  $2,369
$185 off
9/25 - 10/2
$1,779  $1,919
$140 off
10/2 - 10/9
$2,252  $2,445
$193 off
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...

Sea Dog Escape

New to Brindley Beach for 2026!Now offering flex stay (3-nighttime minimum) for the weeks of June 27, 2026 and July 4, 2026.Please Note: This home is located in the heart of Duck Village within walking distance to stores, eateries, and local...

  • Duck
  • 4 Bedrooms
  • 3 Bathrooms
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...

STORM WATCH

Take in the gorgeous ocean-to-sound views in “Storm Watch” in the ships watch; catch the breathtaking sunrise and sunsets. You’ll delight in the charm of this well-maintained oceanside home which features five bedrooms, all with their own...

  • Duck
  • 5 Bedrooms
  • 5.5 Bathrooms
  • Sleeps 10
7/4 - 7/11
$5,099  $5,646
$547 off
9/5 - 9/12
$2,859  $3,096
$237 off
9/12 - 9/19
$2,636  $2,751
$115 off
9/26 - 10/3
$2,521  $2,751
$230 off
10/3 - 10/10
$2,521  $2,751
$230 off
10/10 - 10/17
$2,719  $2,751
$32 off
Nags Head Dolphin Watch

Scientists run these dolphin tours as part of their research on these beloved aquatic animals, so you know this will be an interesting trip. Passengers will be able to see how researchers with the Outer Banks Center for Dolphin Research, a nonprofit...

Surfsong

Classic OBX CondoSurfsong is a coastal condo perfect for a family beach escape. Nestled in the Indian Summer Condominium complex, this upper-level retreat blends the nostalgic feel of classic hardwood walls with updated decor for a clean and modern...

  • Corolla
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
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.