2026 Nags Head Sailing Tours Guide

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Resort Realty Property Management

Celebrating 39 years of service in Outer Banks vacation rental property management, Resort Realty is a company that operates locally with in-house feet on the ground; meaning impeccable care for your home with constant communication from our staff...

Ricky's Retreat 194

Every member of your family will enjoy the original Ricky's Retreat! This fabulous, beautifully decorated home was designed to meet your entire family's every need. Ricky's Retreat services the needs of families of all ages looking for that perfect...

  • Duck
  • 6 Bedrooms
  • 7 Bathrooms
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...

K6513 Four Seasons 11 Bedroom Oceanfront...

Welcome to Four Seasons on Hatteras Island! You will love this brand-new, pet-friendly construction in a unique location in Hatteras Village which gives you both an oceanfront and a soundfront vacation rental. Every room of this home has a...

  • Hatteras
  • 11 Bedrooms
  • 13 Bathrooms
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...

AMIE AND GRAND DUDES

The entire family will enjoy this well-appointed, comfortable oceanside home that is close to the beach and all of the Schooner Ridge amenities. The generous decking will provide a great opportunity to dine while enjoying the gentle ocean...

  • Duck
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 8
6/6 - 6/13
$3,343  $3,704
$361 off
6/27 - 7/4
$3,697  $4,349
$652 off
9/5 - 9/12
$2,192  $2,451
$259 off
9/19 - 9/26
$2,000  $2,172
$172 off
9/26 - 10/3
$2,000  $2,172
$172 off
10/3 - 10/10
$2,000  $2,172
$172 off
10/17 - 10/24
$1,654  $1,788
$134 off
10/24 - 10/31
$1,654  $1,788
$134 off
11/7 - 11/14
$1,599  $1,637
$38 off
Firehouse Boil Delivery

DIY Seafood Boil Don’t Just Make Dinner, Make An Experience! We Deliver on the Outer Banks! Same Day Delivery! Make lasting memories by doing something new with friends and family. Why wait in line at a grocery store or restaurant? Our Low...

SH-4 | Sea Oats

Located One (1) House Back from Ocean. The Summer House Cottages are a group of four identical homes situated on the shores of the Atlantic and are the perfect destination for your family, both immediate and extended. Located in serene South Nags...

  • Nags Head
  • 4 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
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...

Bennett's Bungalow

When all you need is a seaside bungalow close to the beach, then Bennett's Bungalow nicely fits the bill.    Perfect for beach-loving families or couples that want an affordable way to enjoy the beach. And you can do just that via the boarded...

  • Nags Head
  • 2 Bedrooms
  • 1 Bathrooms
Just for the Beach Rentals

Just for the Beach Rentals (not to be confused with the similarly-named "Just for the Beach") offers rentals to accommodate your stay. Equipment includes linens, baby gates, cribs, monitors, seats, joggers, bikes, kayaks, skim boards, surf boards...

Castle on a Cloud

High on the rooftop deck enjoying panoramic ocean views, you will find yourself in “Castle on a Cloud”. Imagine your family in a beautifully decorated beach house with comfortably appointed pool area and shaded picnic and play area for you and...

  • Southern Shores
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
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...

Four-Sea-Sons 590

Four-Sea-Sons is a lovely home with classic Outer Banks style, just 40 yards to the nice, re-nourished beach, and 4th house back from oceanfront! Ideal location for families with small children, this home is located on a quiet cul-de-sac at milepost...

  • Nags Head
  • 4 Bedrooms
  • 2 Bathrooms
5/23 - 5/30
$1,888  $2,088
$200 off
5/30 - 6/6
$2,124  $2,324
$200 off
6/6 - 6/13
$2,421  $2,621
$200 off
6/13 - 6/20
$3,046  $3,246
$200 off
6/20 - 6/27
$3,474  $3,674
$200 off
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.