2026 Nags Head Sailing Tours Guide

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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...

Sandy Beach 356

You and your family will enjoy vacationing in this traditional Kill Devil Hills cottage. Relax and take in the incredible views of the Atlantic from the oceanfront deck. Start your days off right with a cup of coffee and a beautiful sunrise. Spend...

  • Kill Devil Hills
  • 2 Bedrooms
  • 1.5 Bathrooms
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...

FOUR LEAF PLOVER

Overview Top of the morning and the rest of the day as well. May the wind be at your back and the sun upon your face. May your day be filled with Irish blessings, good friends, and great memories! At Four Leaf Plover that is what we...

  • Duck
  • 6 Bedrooms
  • 8 Bathrooms
Jimmy's Seafood Buffet

Home of the Crab Leg & Lobster Buffet for 26! years! Jimmy’s Seafood Buffet is a great stop for an all you can eat affordable dinner extravaganza. The buffet offers over 100 different items. It even serves Jumbo Alaskan crab legs and Jumbo...

Nana's Bananas 458-B

For the best of the Outer Banks visit Nana’s Bananas! This amazing beach house has everything your family could want for an OBX vacation. This home has added features such as a private pool, a tiki area, a hot tub, and a game room, sure to delight...

  • Nags Head
  • 6 Bedrooms
  • 5.5 Bathrooms
6/27 - 7/4
$5,885  $5,990
$105 off
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...

687 | Castle Dune

Enjoy the Royal Life, you'll be treated like royalty, while vacationing at "Castle Dune" located on the Oceanfront in peaceful South Nags Head. This expansive 10 Bedroom estate provides Panoramic Ocean Views and a long list of features that are...

  • Nags Head
  • 10 Bedrooms
  • 7 Bathrooms
  • Sleeps 20
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...

7197 - StillWaters

Always Included, complimentary linens and made beds! NEW FOR 2025: White Oak Hardwood Floors. Welcome to StillWaters, an oceanside retreat located in the charming town of Waves on Hatteras Island...

  • Waves
  • 5 Bedrooms
  • 5 Bathrooms
Sound Feet Shoes

Sound Feet Shoes is family owned and operated. Sound Feet has been in the retail shoe business for over 72 years, opening their first store in 1953. They provide the best customer service and are the only Outer Banks’ area full service shoe...

1915 - Reach the Beach

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! This amazing home will rival any vacation paradise. Located on a large cul-de-sac lot just steps from the beach...

  • Corolla
  • 8 Bedrooms
  • 8.5 Bathrooms
Flip Flop Shops

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



YELLOWTAIL

Carolina Designs presents YELLOWTAIL, a stunning 5-bedroom oceanfront vacation home in Southern Shores featuring an elevator, private pool, hot tub, and premium amenities. This beautifully designed OBX rental combines industrial touches with...

  • Southern Shores
  • 5 Bedrooms
  • 6.5 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.