2026 Nags Head Sailing Tours Guide

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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...

SH-3 | Beach Comber

Located One (1) House Back from Ocean. The Summer House Cottages are a group of four identical homes situated on the shores of the Atlantic and are the perfect destination for your family, both immediate and extended. Located in serene South Nags...

  • Nags Head
  • 4 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
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 Britches

OCEANVIEW Rodanthe - Sea Oats Dr. - SANDY BRITCHES is full of surprises for your next vacation. Take a dip in the private pool or walk to the simple beach access only 4 tons away. When you are done at the beach, stow your gear in the sizable...

  • Rodanthe
  • 4 Bedrooms
  • 4 Bathrooms
Wild Horse Adventure Tours

Wild Horse Adventure Tours has been voted the #1 tour company in the USA by TripAdvisor. Feel the ocean breeze and taste the salty beach air as you cruise the Outer Banks beaches in our exclusive OPEN AIR, 13-passenger Hummers with one of...

EGRET'S LANDING

Egret's Landing is a seven bedroom oceanfront Carolina Designs home in Corolla's Whalehead community. Ocean vistas follow you from almost every angle of this bright, airy retreat. Spacious and thoughtfully decorated with modern beach house...

  • Corolla
  • 7 Bedrooms
  • 7 Bathrooms
Bob's Wild Horse Adventure Tours

Welcome to Bob’s Wild Horse Adventure Tours, Corolla’s #1 source for family fun since 1996 and voted Best Wild Horse Tour in the Reader's Choice BEST of OBX contest! We offer guided tours to see the Corolla Wild Horses in several ways...

Sunsets in Rodanthe

OCEANSIDE Rodanthe — S. Holiday Blvd. — What can possibly surpass catching the sun emerging from the ocean to signal the start of another impressive day? How about the way it descends into the sound in a blaze of deep hues as the evening...

  • Rodanthe
  • 4 Bedrooms
  • 3.5 Bathrooms
Big Buck's Homemade Ice Cream

Serving our customers on the Outer Banks since 1994, Big Buck's ice Cream is dedicated serving you “The Best.” We offer a full line of super-premium ice cream products, smoothies, chocolates, and custom-made ice cream cakes! 2 locations...

095 | Sweet Virginia Breeze

Outstanding design & beautiful decor combine to make this vacation home a wonderful choice for your family’s Outer Banks retreat. Located in the desirable Old Nags Head Place community, this home is spacious, fully equipped, & offers...

  • Nags Head
  • 7 Bedrooms
  • 5.5 Bathrooms
  • Sleeps 14
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...

Sound Therapy

SOUNDSIDE Avon — Kinnakeet Shores — Let nature take its course at SOUND THERAPY and wrap you in the peaceful beauty of Pamlico Sound, home to one of the best kiteboarding and windsurfing spots on the East Coast. With seven decks offering...

  • Avon
  • 7 Bedrooms
  • 7.5 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...

Dad's Mercedes, Mom's Dream

Located in Corolla / 4 Bedrooms / 3 Full Bathrooms / 1 Half BathroomThis Corolla getaway is designed to impress, offering a welcoming coastal escape in the sought-after Corolla Bay community just over 1,000 feet from beach access. Thoughtfully...

  • Corolla
  • 4 Bedrooms
  • 3 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.