2026 Nags Head Sailing 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...

Boxley House

CANALFRONT Frisco — Captains Ct. — Rustic appeal abounds in BOXLEY HOME, a three-bedroom/two-bathroom home that offers a relaxing setting in Brigands' Bay, a bicycle-friendly neighborhood known for its canal “streets.” Bring your...

  • Frisco
  • 3 Bedrooms
  • 2 Bathrooms
KEES Vacations

KEES Vacations offers the best Outer Banks rentals for family vacations, romantic weekend getaways and groups of all sizes looking for the perfect OBX rental for their stay. When booking with KEES Vacations, travelers can expect excellence in...

2910 - Dolphin's Den

Always Included, complimentary linens and made beds! An oceanfront condo perfect for a Duck escape! Dolphin's Den is a 2 bedroom, 2 bathroom Outer Banks condo rental ready for you and your family to...

  • Duck
  • 2 Bedrooms
  • 2 Bathrooms
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...

Sunset Dreams 283-B

Come to Kitty Hawk and live your Sunset Dreams!This delightful soundfront home has been recently renovated and is in immaculate condition. With a spacious layout, your family will have ample room so you are comfortable and able to relax while on...

  • Kitty Hawk
  • 4 Bedrooms
  • 4 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...

464 | Tuna Daze

This Outstanding Semi-Oceanfront Beach Home offers Beautiful Decor, Comfortable Furnishings, Ocean Views, & has Direct Beach Access (Across Beach Road). The perfect get-a-way for your family vacation or romantic escape, this home is ideally...

  • Kitty Hawk
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Ben Franklin

Stop by Nags Head's Ben Franklin at Mile Post 10 on the Bypass where you will find everything you need for the beach! From Clothing, T-shirts and Swimwear to Boards, Chairs, Umbrellas and Tackle. You'll find it all…and of course, we have the...

The Sleepy Dog

OCEANVIEW Salvo - Colony Drive - If you're looking for a home to accommodate your group with a nice selection of amenities in a great location and at a good value, try THE SLEEPY DOG. Just 3 tons from the beach, access is just a short walk away. The...

  • Salvo
  • 5 Bedrooms
  • 3 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...

817 | Hill Ocean 2

Hill Ocean II is a wonderful - Dog Friendly vacation home that is perfect for your next family vacation on the OBX. Located on a beautiful stretch of beach in Nags Head right on the Oceanfront, this 4 bedroom unit is a Private enough to be rented...

  • Nags Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Firehouse Boil Delivery

DIY Seafood Boil Don’t Just Make Dinner, Make An Experience! We Deliver on the Outer Banks! Same Day Delivery! Make lasting memories by doing something new with friends and family. Why wait in line at a grocery store or restaurant? Our Low...

Barefootn'

SEMI-OCEANFRONT Avon - Oceanview Drive - Ready to go BAREFOOTN'? Then it's time for some fun at this beach home just across the street from the beach. Ground level amenities include carport, dry entry, outdoor shower, fish cleaning table, charcoal...

  • Avon
  • 4 Bedrooms
  • 3.5 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.