2026 Nags Head Sailing Tours Guide

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Outer Banks Blue

Since 2005, Outer Banks Blue has delivered exceptional vacations for OBX visitors. Our family-owned and locally managed rental company focuses on service and promises “a relaxing experience with a local touch.” Turn your dream vacation...

Dream Catcher

With 8 Bedrooms, a Private Pool and Direct Access to the Beach, this beautiful oceanfront home is the perfect escape for you and your family group to enjoy an idyllic Outer Banks vacation in Nags Head. Enjoy spectacular ocean views from the...

  • Nags Head
  • 8 Bedrooms
  • 6 Bathrooms
Big Buck's Homemade Ice Cream

Serving our customers on the Outer Banks since 1994, Big Buck's ice Cream is dedicated serving you “The Best.” We offer a full line of super-premium ice cream products, smoothies, chocolates, and custom-made ice cream cakes! 2 locations...

Forty Steps Closer 56-D

Forty Steps Closer is a stunning semi-oceanfront home in Corolla, offering countless amenities sure to please the whole family. Located just steps from the beach in the Ocean Sands neighborhood, Forty Steps Closer was thoughtfully designed...

  • Corolla
  • 8 Bedrooms
  • 9 Bathrooms
5/31 - 6/7
$8,389  $10,094
$1,705 off
6/7 - 6/14
$10,669  $12,374
$1,705 off
7/5 - 7/12
$15,737  $16,737
$1,000 off
7/12 - 7/19
$15,737  $16,737
$1,000 off
Back Country Safari Tours

Discover wild Spanish Mustangs and our unique Barrier Island ecology on the Wild Horse Safari. Explore over 30 miles of "off road" beach, dune and sand trail and ride with a professional naturalist guide in a custom 4x4 open-air Safari Cruiser, or...

Port O'Call III 537-B

This classic, 4-bedroom vacation home at milepost 17.5 in South Nags Head is just waiting for you and your family. With a shared walkway, the beaches of South Nags Head are only 200 feet away! Just a short car ride to shopping, water sports...

  • Nags Head
  • 4 Bedrooms
  • 2.5 Bathrooms
Cosmo's Pizzeria Southern Shores

If you're searching for great pizza on the Outer Banks, look no further than Cosmo's Pizzeria at The Marketplace in Southern Shores! We offer authentic New York-style pizza made fresh and just the way you like, using only the highest quality...

5420 - The Galleon
  • Nags Head
  • 4 Bedrooms
  • 3 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...

Lucky Paws Escape

Welcome to Lucky Paws Escape, a bright and adorable semi-oceanfront retreat located in the heart of Nags Head at Milepost 16.0. This charming 4-bedroom, 3.5-bathroom dog-friendly home is perfect for families and pet lovers alike, offering a long...

  • Nags Head
  • 4 Bedrooms
  • 3 Bathrooms
Brindley Beach Vacations

Brindley Beach Vacations offers premier Real Estate and Property Management services across the entire Outer Banks. Representing more than 450 vacation rental homes, we proudly serve every region—from the southern beaches of Hatteras Island...

4601 - Sandy Bluff

Always Included, complimentary linens and made beds! The "Sandy Bluff" cottage offers the perfect opportunity for a beach vacation from a home nestled in a tranquil Southern Shores neighborhood...

  • Southern Shores
  • 4 Bedrooms
  • 4 Bathrooms
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...

CAROLINA CABANA

Overview If you're in search of equal parts of fun and relaxation, let Carolina Cabana be your next vacation destination! This bright and cheerful home is designed with family gatherings in mind and is located in Four Seasons, an...

  • Duck
  • 6 Bedrooms
  • 5.5 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.