2026 Nags Head Sailing Guide

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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...

241 | Rise-n-shine

This lovely Nags Head Beach Cottage is located only 1 block from the Beach w/Direct Access at Barnes Street & is an excellent vacation choice! Recently updated and very nicely decorated, this well equipped home has a great location for you and...

  • Nags Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
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...

A Shore Thing VP-204

Welcome to A Shore Thing, a two-bedroom, two-bathroom pet-friendly condo featuring a spacious design with an open layout, high-end furnishings, and tasteful decor. Perfect for entertaining inside or out on your own oversized private deck and just...

  • Kill Devil Hills
  • 2 Bedrooms
  • 2 Bathrooms
The Cotton Gin

For those traveling to the Outer Banks, The Cotton Gin is a beloved landmark with its large windmill and picturesque gardens. The Cotton Gin has stood in the same location since 1929, starting as a working cotton gin and growing to a gift store with...

Sail Right Up

SOUNDFRONT Avon — Bluefish Ct — It’s nothing but smooth sailing when you settle into SAIL RIGHT UP, a four-bedroom/two-bath home with an enviable elevated perch to maximize the glorious vistas of Pamlico Sound. Let the water soothe your soul...

  • Avon
  • 4 Bedrooms
  • 2 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...

Sailor's Delight

OCEANVIEW Hatteras – Slash Creek Rd. – Vacation is always a enjoyment when you stay at SAILOR’S DELIGHT. With all level decks, spectacular vistas, and plenty of parking, this home is sure to delight everybody. Laze around in the fenced-in...

  • Hatteras
  • 6 Bedrooms
  • 5.5 Bathrooms
Kitty Hawk Kites

Looking to fly a kite on the beach or atop the spectacular dunes of Jockey’s Ridge State Park? Kitty Hawk Kites offers the largest selection of kites, wind art, flags, games, and toys on the Outer Banks, with experts on staff to get you flying...

THE DUCK HOUSE

“The Duck House” will be your idea of the ultimate beach vacation with beautiful views of the scenic North Carolina sunrises over the Atlantic from this spectacular oceanfront home. This home was designed with your group's comfort in mind, every...

  • Duck
  • 5 Bedrooms
  • 7.5 Bathrooms
  • Sleeps 10
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...

2865 - Heaven Sent

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! NEW FOR 2026: Hot Tub, Carpet, Level 1 Theatre Room Couch. From the moment you see "Heaven Sent" perched high atop...

  • Duck
  • 7 Bedrooms
  • 7.5 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...

Salty Dog

Salty Dog is a charming, oceanside vacation home perfect for relaxing on your Outer Banks getaway. This property features ocean views from the upper-floor deck and a sunroom that includes both a dining room and a reading area. The interior has a...

  • Corolla
  • 3 Bedrooms
  • 2 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.