2026 Nags Head Sailing Tours Guide

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Carolina Designs Realty

Plan your Outer Banks vacation with Carolina Designs! Browse our inventory of 350+ select Outer Banks vacation rentals located in the towns of Corolla, Duck, Southern Shores, Kitty Hawk, Kill Devil Hills, and Nags Head. Book online anytime, or reach...

TWO BUOYS

Overview A vacation at Two Buoys is sure to be the talk of your group for years to come, and maybe even a new tradition. This seven-bedroom beach retreat, less than a half-mile from the beach, and only a few minute walk into town, is...

  • Duck
  • 7 Bedrooms
  • 7.5 Bathrooms
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...

Sunset Pleasure

SOUNDSIDE Avon – Kinnakeet Shores Resort – The enjoyment is all ours to introduce SUNSET PLEASURE, a majestic seven-bedroom/seven full- and one-half-bath home that promises to enthrall from sunrise to sunset with elegantly designed spaces...

  • Avon
  • 7 Bedrooms
  • 7.5 Bathrooms
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...

VH208 Sea Edge at Villas of Hatteras Lan...

Welcome to the Sea Edge at the Villas of Hatteras Landing by KEES Vacations! Rarely do getaways have a smaller getaway built into them, but that's exactly what you will find at Hatteras. While the Outer Banks is a place overflowing with culture and...

  • Hatteras
  • 1 Bedrooms
  • 1 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...

Fun Factory

OCEANSIDE Waves – Island Pines Dr. — FUN FACTORY is not just a beach home; it's a sanctuary for those who crave relaxation and memorable memories where every moment is an opportunity to embrace life to the fullest. Freshly constructed in a...

  • Waves
  • 4 Bedrooms
  • 3 Bathrooms
Salt Coast Outfitters

We offer one of a kind SALT COAST OUTFITTERS brand name tees, long sleeves, performance gear, Yeti tumblers, caps, eyeglasses, and more! Browse the fullest collection of coastal lifestyle clothing on the beach. Featuring a sizable selection of brand...

Montana Mermaid 504

With amenities abound including a private pool, an elevator, and ocean views, everyone in the family will enjoy their Outer Banks beach vacation at Montana Mermaid! Guests will also enjoy a spacious floor plan, large game room, and large living...

  • Nags Head
  • 8 Bedrooms
  • 8.5 Bathrooms
Kitty Hawk Surf Co.

Experience more adventure, fun, and style with Kitty Hawk Surf Company. As the trusted Outer Banks retailer for all top surf and lifestyle brands, including, Hurley, Billabong, RVCA, The North Face, Patagonia, Salt Life, Salty Crew, Volcom...

Sea-Fantasy

OCEANFRONT Hatteras — Durant Station Condo, Unit 210 — SEA-FANTASY is everything its name implies. With spectacular ocean and sound vistas from private decks on both sides, you can watch the sun both rise and set as your imagination plays with...

  • Hatteras
  • 1 Bedrooms
  • 1 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...

FIVE O CLOCK SOMEWHERE

Relax and enjoy every special moment that you and your family spend in this 3,600 square foot, five bedroom, upscale home. A beautifully appointed home with wonderful views, Five O’Clock Somewhere sits on a spacious lot (2/3 acre) in one of the...

  • Southern Shores
  • 5 Bedrooms
  • 5.5 Bathrooms
  • Sleeps 12
9/6 - 9/13
$2,836  $3,048
$212 off
9/13 - 9/20
$2,527  $2,754
$227 off
9/20 - 9/27
$2,527  $2,754
$227 off

Kitty Hawk Kites’ Whalebone Watersports Center is your one-stop shop for Outer Banks water adventures. Located on the Nags Head-Manteo Causeway right on Roanoke Sound, this location offers it all – dolphin watching cruises with a marine...