2026 Nags Head Sailing Tours Guide

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Jolly Roger

When you first catch sight of The Jolly Roger, you might be unsure exactly what to think of it. Since its conversion from a gas station/grocery store to a restaurant in 1972, The Jolly Roger has been anything but your ordinary Outer Banks...

COASTAL LEGASEA

Overview Oceanfront in Nags Head, Coastal LegaSea is sure to be the backdrop of the vacation stories you'll tell for years to come. Loaded down with amenities to enjoy while spending your days on the Outer Banks, this home has a...

  • Nags Head
  • 8 Bedrooms
  • 10 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...

CB31 - Shore Slackers Whelkome

Always Included, complimentary linens and made beds! NEW FOR 2026: Dishwasher, ice maker, and exterior house paint. Pet friendly, luxe, and in the middle of it all lies Shore Slackers Whelkome! This...

  • Corolla
  • 4 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...

665 | Explorers Oasis

This Gorgeous Beach Home is the perfect vacation destination for your family, offering many lovely touches along with amenities that are sure to please. Plus, Beach access is an easy 150 foot walk away at E. Lake Drive. Well-equipped to ensure a...

  • Kill Devil Hills
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
8/22 - 8/28
$3,295  $3,495
$200 off
Black Pelican

Black Pelican oceanfront restaurant is one of the Outer Banks’ premier restaurants serving lunch and dinner daily. Black Pelican is where you can enjoy fresh seafood, steaks, vegetarian dishes, sandwiches and some of the barrier island’s...

452 | Beach Runner

Nicely decorated, comfortable, and well-maintained, Beach Runner cottage is a short walk to the Beach Access (direct access to Admiral Street Beach Access) and a short walk to the local grocery store. The home is well equipped w/TV's in each...

  • Nags Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
7/5 - 7/11
$2,195  $2,395
$200 off
7/12 - 7/18
$2,195  $2,395
$200 off
Paradise Fun Park

Off the beach, one of the best activities for groups to enjoy in the Outer Banks is mini golf, bumper cars or Go-Karts. Thankfully, Paradise Fun Park offers all three activities! Paradise Fun Park offers exciting outdoor activities that kids and...

OC6 The Purser's Cottage at Oceanside Co...

Welcome to The Purser's Cottage at Oceanside Court by KEES Vacations! These quaint oceanfront cottages are the perfect place for you and your family to have a unique and unforgettable vacation offering the perfect balance between amenities and...

  • Nags Head
  • 2 Bedrooms
  • 1 Bathrooms
Miss Oregon Inlet

Oregon Inlet Fishing Center is the home of the largest and most modern charter boat fishing fleet on the eastern seaboard. A full service marina in Nags Head NC, Oregon Inlet offers a comprehensive charter boat fishing experience for the "old salt...

Farrview

Now Offering Flex Stay All Year Long (3-nighttime Minimum)Located in Duck / 4 Bedrooms / 3 Full Bathrooms / 1 Half BathroomTake in the spectacular vistas of the Currituck Sound and Atlantic Ocean from the decks at this well-maintained home located...

  • Duck
  • 4 Bedrooms
  • 3 Bathrooms
Bodie Island Lighthouse

The Bodie Island Lighthouse, (pronounced "Body") is located just south of the town of Nags Head and Whalebone Junction, where Highway 158, Highway 64, and NC Highway 12 intersect. Visitors travelling towards Hatteras Island can't help but notice the...

K6401 Hatteras Retreat Oceanfront 7 Bedr...

Welcome to Hatteras Retreat by KEES Vacations! This home will re-open beginning June 15th, 2026 with a new pool, hot tub, and oceanfront location! Buxton experienced erosion in late 2025, subsequently, this home has been moved from its original...

  • Buxton
  • 7 Bedrooms
  • 7 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.