2026 Nags Head Sailing Guide

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Mike Dianna's Grill Room

Welcome to Mike Dianna's Grill Room, home to the finest seafood, USDA prime beef, amazing live entertainment and more! Come have brunch or dinner with us in Corolla on the beautiful Outer Banks. Celebrating over 20 years in the Timbuck II Shopping...

Sea Song

Located in Corolla / 4 Bedrooms / 3 Full BathroomsYour family will surely be "singing" the praises of this well-maintained home with it's bright, beachy colors and coastal decor. Located near the ocean and within painless reach of Corolla favorites...

  • Corolla
  • 4 Bedrooms
  • 3 Bathrooms
Flip Flop Shops

Free Your Toes!®Live, work and play with your toes exposed® and the freedom of flip flops on your feet. 



Ultra Classic

Monterey Shores' Classic RetreatRelax at the beautiful Corolla vacation rental, Ultra Classic! A 4-bedroom, 2-bathroom property in the Monterey Shores community, you'll love the Tuscan-inspired architecture and secluded, forested lot with plenty...

  • Corolla
  • 4 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
OBX Ghost Tours

OBX Ghost tours is something your family will be talking about the rest of the summer! You'll be entertained as a guide leads you through down town Manteo by lantern telling the spooky stories that makes The Outer Banks one of the most haunted...

308 | Family Tides

Spend your dream vacation on the Nags Head Oceanfront in this beautiful home. After working hard all year, you deserve rest & relaxation. This elegant getaway is just what the doctor ordered. Enjoy sweeping views of the Atlantic, relax by the...

  • Nags Head
  • 6 Bedrooms
  • 5.5 Bathrooms
  • Sleeps 14
Henry's Restaurant

Henry's Restaurant offers down home, simple food done Outer Banks style. Henry's Restaurant has been serving the Outer Banks of North Carolina since the summer of 1989. They are pleased to be considered one of the most popular restaurants in Dare...

5726 - Ellington Cottage By The Sea

Always Included, complimentary linens and made beds! Perched along the scenic shoreline of South Nags Head, Ellington Cottage by the Sea offers an authentic oceanfront Outer Banks escape. This...

  • Nags Head
  • 6 Bedrooms
  • 6 Bathrooms
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...

The Sand Jewel

OCEANFRONT Avon — Not a morning person? That may change when you catch the sunrise from THE SAND JEWEL’s wide deck overlooking the dunes and the Atlantic coastline. The glorious site has been known to color your imagination on how great a day...

  • Avon
  • 4 Bedrooms
  • 3 Bathrooms
Brew Thru

No trip to the Outer Banks is complete without cruising through Brew Thru, the Outer Banks’ original drive thru convenience store. Whether you’re looking for a refreshing cold beverage of Coke, Pepsi and other soft drinks on the go...

5548 - Toes In The Sand

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! NEW FOR 2026: New carpeting throughout the property, new hot tub, and new gravel parking spot at the front of the...

  • Nags Head
  • 6 Bedrooms
  • 6.5 Bathrooms
Gray's

Gray’s Outer Banks Lifestyle Clothing Company offers the absolute best in Outer Banks T-shirts and Sweatshirts including Champion, Under Armour with "Outer Banks” and Gear! We carry quality fashions and accessories for the whole family...

612 | Needlepoint Dunes

Experience sweeping Atlantic and Jockey's Ridge largest sand dune) views from Needlepoint Dunes, a beautifully appointed oceanfront retreat in the Nags Head Historic District. Carefully maintained as the owners second home and available only a few...

  • Nags Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
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.