2026 Nags Head Sailing Tours Guide

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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...

THE LAST RESORT

Granted, the panoramic ocean and sound views can't be beat, but what really sets this home apart is the beauty to be experienced inside the immaculately maintained house. The owners, two sisters who grew up vacationing on the OBX, have made The...

  • Duck
  • 4 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
8/30 - 9/6
$1,558  $1,833
$275 off
9/6 - 9/13
$1,469  $1,710
$241 off
9/27 - 10/4
$1,328  $1,496
$168 off
10/4 - 10/11
$1,334  $1,496
$162 off
10/11 - 10/18
$1,334  $1,496
$162 off
10/18 - 10/25
$1,322  $1,372
$50 off
10/25 - 11/1
$1,322  $1,372
$50 off
11/1 - 11/8
$1,171  $1,222
$51 off
11/8 - 11/15
$1,172  $1,222
$50 off
11/15 - 11/22
$1,195  $1,222
$27 off
Flip Flop Shops

Free Your Toes!®Live, work and play with your toes exposed® and the freedom of flip flops on your feet. 



5232 - Peaceful Easy Feeling

Always Included, complimentary linens and made beds! NEW FOR 2026: LVP flooring in living area and kitchen. You’ll be sure to get that Peaceful Easy Feeling at this Outer Banks vacation home...

  • Kill Devil Hills
  • 4 Bedrooms
  • 4 Bathrooms
OBX Ghost Tours

OBX Ghost tours is something your family will be talking about the rest of the summer! You'll be entertained as a guide leads you through down town Manteo by lantern telling the spooky stories that makes The Outer Banks one of the most haunted...

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
9/27 - 10/4
$2,626  $2,871
$245 off
Mike Dianna's Grill Room

Welcome to Mike Dianna's Grill Room, home to the finest seafood, USDA prime beef, amazing live entertainment and more! Come have brunch or dinner with us in Corolla on the beautiful Outer Banks. Celebrating over 20 years in the Timbuck II Shopping...

SURF AND SOUND

Discover Surf and Sound in Corolla, a Carolina Designs OBX vacation rental set soundfront on a large lot at the end of a quiet cul-de-sac. This five bedroom Outer Banks retreat pairs a private dock and sunset views with a 30 x 14 private pool...

  • Corolla
  • 5 Bedrooms
  • 4.5 Bathrooms
Paradise Dolphin Cruises

With the best views around and the quickest access to dolphins, Paradise Dolphin Cruises is committed to offering you one of the most amazing experiences of your life! Climb aboard the Kokomo, our 34-passenger catarmaran and the area’s newest...

Sea Turtle OCS-61

Located in the charming setting of South Nags Head with easy beach access (approx. 600' away), Sea Turtle is a well-appointed home, perfect for entertaining the whole family while on vacation, featuring 4 bedrooms and 4.5 baths. The beautiful...

  • Nags Head
  • 4 Bedrooms
  • 4.5 Bathrooms
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...

Angels' Retreat

Gather your family and friends to getaway to the beach and soak up all there is to love about the Outer Banks right near the Corolla Lighthouse! If your vacation plans include a pet friendly home with a private heated 16x32  pool, cabana by the...

  • Corolla
  • 12 Bedrooms
  • 12 Bathrooms
9/8 - 9/15
$5,202  $5,797
$595 off
9/9 - 9/16
$5,255  $10,302
$5,047 off
9/20 - 9/27
$4,855  $5,177
$322 off
OBX Shipping Center

We are the only Authorized Shipping Center on the OBX for FedEx, UPS and DHL. Come to OBX Shipping Center for all your shipping and office needs. We offer Notary services, copies, faxing, laminating, among other office services. You do the...

Sea And Sand 245

Experience gorgeous ocean views from this lovely vacation home! Sea and Sand is equipped with everything you need for a great Outer Banks family vacation. Just 50 feet across Rt-12 you have an access shared by just a few homes perfect for your...

  • Kitty Hawk
  • 4 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.