2026 Nags Head Sailing Tours Guide

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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...

Sail On

SOUNDFRONT Hatteras - Ellwood Ct. - SAIL ON is a huge, bespoke-designed home constructed on a bulkheaded peninsula in Hatteras Village. With its broad vistas of the sound, it simply can't be beat. Savor the private pier with 2 boat slips (approx...

  • Hatteras
  • 4 Bedrooms
  • 3.5 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...

MACWATER BEACH HOUSE

“MacWater Beach House” is a timeless, 5-bedroom oceanfront home in Southern Shores offering the perfect blend of classic charm and comfort. Enjoy breathtaking ocean views and breezes from the top floor sun deck, perfect for sunbathing and simply...

  • Southern Shores
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
10/10 - 10/17
$2,973  $3,602
$629 off
10/17 - 10/24
$2,411  $2,856
$445 off
10/24 - 10/31
$2,496  $2,856
$360 off
10/31 - 11/7
$2,496  $2,706
$210 off
11/7 - 11/14
$2,346  $2,706
$360 off
11/14 - 11/21
$2,483  $2,706
$223 off
11/28 - 12/5
$2,483  $2,706
$223 off
12/5 - 12/12
$2,551  $2,706
$155 off
12/12 - 12/19
$2,620  $2,706
$86 off
Lost Treasure Golf

The noted explorer, archaeologist, anthropologist, paleontologist, and part-time plumbing contractor from the University of Chicago, Professor Duffer A. Hacker, led two expeditions to the outer banks in the late 1920’s. The purpose of these...

190 | Indigo Run

Our Indigo Run is an outstanding, beautifully decorated vacation retreat that provides Ocean to Sound Views & easy access to the Beach. All the extras are here to make your stay complete & your family will love the luxury of having your own...

  • Nags Head
  • 6 Bedrooms
  • 6.5 Bathrooms
  • Sleeps 14
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...

Hatteras Memories

SEMI-OCEANFRONT Hatteras — Slash Creek Rd — New for 2027! — A short walk from the sand leads you to HATTERAS MEMORIES, a five-bedroom/four-full and one-half-bath home that invites you to spend your days soaking up the sun and spectacular...

  • Hatteras
  • 5 Bedrooms
  • 4.5 Bathrooms
Poke Box

PokeBox offers fresh, quick, simple, healthy poke bowls in Nags Head. Choose your items and build your bowl. Tuna, salmon, chicken, steak, shrimp and tofu options available. Mix in your favorite veggies, sauces and toppings for the perfect poke...

Aqua Holic

Located in Corolla / 5 Bedrooms / 4 Full Bathrooms / 1 Half BathroomArrive early and appreciate a Currituck Club pre-arrival experience at the main pool between 10 am and 4 pm! Games, trolley service to and from the beach, music, wine, food &...

  • Corolla
  • 5 Bedrooms
  • 4 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...

Cabana Beach

Located in Corolla / 7 Bedrooms / 7 Full BathroomsThis oceanfront home offers spectacular unobstructed ocean and sound vistas. Cooking is a delight with gourmet appliances and breath taking vistas. Savor the comfort and ease of life at the beach...

  • Corolla
  • 7 Bedrooms
  • 7 Bathrooms
Miller's Waterfront Restaurant

MILLER’S OFFERS ONE OF THE FEW TRULY WATERFRONT DINING EXPERIENCES ON THE OUTER BANKS. Enjoy casual dining in our downstairs family-friendly seafood restaurant, or our signature drinks and grill menu in our upstairs deck bar while watching...

Baby's Dream 315

Baby’s Dream is a place to vacation with all the comforts of home. This intimate beach home has 4 bedrooms, 3 of which are en suites, and is perfect for a family vacation or a couples’ getaway. Views of the Atlantic are sure to help you unwind...

  • Kill Devil Hills
  • 4 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.