2026 Nags Head Sailing Tours Guide

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KEES Vacations

KEES Vacations offers the best Outer Banks rentals for family vacations, romantic weekend getaways and groups of all sizes looking for the perfect OBX rental for their stay. When booking with KEES Vacations, travelers can expect excellence in...

THE CIRCLE R

Relax at this cozy beach cottage, “The Circle R” in Southern Shores, located Oceanside off of Route 12 (Duck Road) Between Kitty Hawk and Duck. You will immediately feel at home when you walk in, finding a very comfortable environment with...

  • Southern Shores
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
8/21 - 8/28
$2,358  $2,456
$98 off
8/28 - 9/4
$2,005  $2,159
$154 off
9/18 - 9/25
$1,648  $1,764
$116 off
Bob's Wild Horse Adventure Tours

Welcome to Bob’s Wild Horse Adventure Tours, Corolla’s #1 source for family fun since 1996 and voted Best Wild Horse Tour in the Reader's Choice BEST of OBX contest! We offer guided tours to see the Corolla Wild Horses in several ways...

SEA ESCAPE

Delightful home in Duck Landing with private beach access and a short walk to Duck Village shops and restaurants. 345 yards to beach access.Level 1:Bedroom (with Queen). Recreation room TV, DVD player, Foosball, full refrigerator with ice maker...

  • Duck
  • 6 Bedrooms
  • 6.5 Bathrooms
  • Sleeps 16
7/11 - 7/18
$7,171  $8,328
$1,157 off
7/25 - 8/1
$7,171  $8,328
$1,157 off
8/22 - 8/29
$4,880  $5,633
$753 off
American Pie

Discover the best homemade ice cream and authentic made-from-scratch New York Style pizza the Outer Banks has to offer at American Pie in Kill Devil Hills. An Outer Banks favorite for lunch, dinner or a delicious scoop of scrumptious ice cream after...

K5308 Soundside Breeze at Pirate's Cove

Welcome to Soundside Breeze by KEES Vacations! If you are looking for comfortable and charming, look no further than Soundside Breeze! This bright and cheerful first-level end unit can accommodate up to 6 guests and offers a King bedroom, private...

  • Manteo
  • 1 Bedrooms
  • 1 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...

K7200 Saltaire 8 Bedroom Home at Water O...

Welcome to Saltaire by KEES Vacations! NEW FOR 2026: Be among the first to stay in this brand-new rental, never before rented. Your stay also includes exclusive access to the Village Beach Club! Saltaire, where timeless elegance meets modern coastal...

  • Kill Devil Hills
  • 8 Bedrooms
  • 8 Bathrooms
Resort Realty

For more than 39 years, Resort Realty has been providing unforgettable Outer Banks vacations. From Corolla to Hatteras Island, Resort Realty offers nearly 600 Outer Banks vacation homes that range from cozy 1-bedroom condos to exquisite 20-bedroom...

CAROLINA SUNRISE

Bright and airy home on beautiful and conveniently located Circle Drive. Spacious pool deck in private treed area. Three levels of sun and shaded decks. Lighted rooftop deck with 360 degree views.Level 1:3 bedrooms (1 with Queen, CATV, and private...

  • Southern Shores
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
6/26 - 7/3
$3,598  $4,621
$1,023 off
7/10 - 7/17
$3,803  $4,621
$818 off
7/31 - 8/7
$4,124  $4,621
$497 off
8/14 - 8/21
$3,178  $3,477
$299 off
8/21 - 8/28
$3,008  $3,194
$186 off
8/28 - 9/4
$2,527  $2,781
$254 off
9/4 - 9/11
$2,288  $2,578
$290 off
9/11 - 9/18
$2,073  $2,284
$211 off
9/18 - 9/25
$2,126  $2,284
$158 off
9/25 - 10/2
$1,989  $2,161
$172 off
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...

The Purple Whale 493

The Purple Whale is a semi-oceanfront coastal retreat offering a charming interior, inviting outdoor deck space, and a prime location near the beach, shopping, and some of the best dining Nags Head has to offer! Also, don't forget your furry family...

  • Nags Head
  • 3 Bedrooms
  • 2 Bathrooms
6/27 - 7/4
$3,952  $4,352
$400 off
Fish Heads Bar and Grill

Rustic waterfront pub at a fishing pier with a large deck for seafood eats, draft beer & live music. Fish Heads Bar and Grill is THE tiki bar of the Outer Banks. Located at Mile Post 18.5 in Nags Head, we offer a view that is second to none...

Relax Mom

New for 2026: Replaced mid-level to bottom level deck stairs, new bottom level refrigerator with water dispenser, beach storage shed through Corolla Beach Units and a new ground level King bed frame. Located in Corolla / 5 Bedrooms / 4 Full...

  • Corolla
  • 5 Bedrooms
  • 4 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.