2026 Nags Head Sailing Guide

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Pigman's Bar-B-Que

You haven’t experienced North Carolina until you’ve experienced North Carolina BBQ, and Pigman’s Bar-B-Que offers excellent North Carolina BBQ meals served with southern hospitality. Pigman’s offers traditional eastern...

3942 - My Tern

Always Included, complimentary linens and made beds! Welcome home to My Tern the perfect Duck vacation rental! Located in the Schooner Ridge community in Duck, you'll be close to everything this...

  • Duck
  • 4 Bedrooms
  • 4.5 Bathrooms
Flip Flop Shops

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



5727 - Whalebone Station

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Whalebone Station is centrally located on the beautiful Outer Banks of North Carolina. Located at the very beginning...

  • Nags Head
  • 9 Bedrooms
  • 10 Bathrooms
Paradise Dolphin Cruises

With the best views around and the quickest access to dolphins, Paradise Dolphin Cruises is committed to offering you one of the most amazing experiences of your life! Climb aboard the Kokomo, our 34-passenger catarmaran and the area’s newest...

Captain's Belle

SOUNDSIDE Avon - Kinnakeet Shores - Don't wait to book your date with CAPTAIN'S BELLE. Located in family friendly Kinnakeet Shores, start your vacation off right with a walk to the beach via the convenient boardwalk across the lake, just one lot...

  • Avon
  • 5 Bedrooms
  • 4.5 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 PENNY SWAN

“The Penny Swan” will be your picture perfect Outer Banks beach vacation home! You will be so close to the beach you will experience the warm and breezy ocean air from this property's spacious sun and covered decks, 14 x 28 private saltwater...

  • Southern Shores
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 18
Fish Heads Bar and Grill

Rustic waterfront pub at a fishing pier with a large deck for seafood eats, draft beer & live music. Fish Heads Bar and Grill is THE tiki bar of the Outer Banks. Located at Mile Post 18.5 in Nags Head, we offer a view that is second to none...

SEAHAWK

Overview Yankee practicality and southern charm infuse to bring you Seahawk, a cheerful Duck home designed to be an ideal beach retreat for any time of the year. Inviting and comfortable, this soundside escape offers refuge in one of...

  • Duck
  • 5 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...

023 | Serenity Now

This Beachfront Estate provides outstanding Ocean Views and promises a truly memorable family vacation. Designed in the traditional Nags Head cedar shake style, this modern home is beautifully decorated and furnished w/every Amenity to ensure your...

  • Nags Head
  • 8 Bedrooms
  • 6.5 Bathrooms
  • Sleeps 18
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...

ENDLESS SUMMER II

Fully Renovated including all new bathrooms, kitchen, furniture, flooring, decor, all new mattresses & bedding! ENDLESS SUMMER 2 is the ideal location with panoramic sunrise & sunset views, With only 1 house between you and the ocean, you're...

  • Southern Shores
  • 6 Bedrooms
  • 6.5 Bathrooms
  • Sleeps 14
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.