2026 Sailing Tours Guide

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



SANDY CHATEAU

Overview If your objective is to spend endless days lounging on sandy beaches, the ocean access is a short walk from Sandy Chateau, and the serene streets ensure quiet strolls to both the waterfront and to sightsee in Duck. A multi-use...

  • Duck
  • 8 Bedrooms
  • 8.5 Bathrooms
Miller's Seafood and Steakhouse

Miller's Seafood & Steakhouse has been a favorite among locals and visitors for more forty years. Offering delicious southern cuisine for both breakfast and dinner in a casual family atmosphere infused with coastal flair, it's no wonder this...

5821 - Sugar Magnolia

Always Included, complimentary linens and made beds! NEW FOR 2026: Roof and Hot Tub. Home will be Pet Free for 2027 A home that’s fit for your family’s needs, Sugar Magnolia has it all! This...

  • Nags Head
  • 7 Bedrooms
  • 8 Bathrooms
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...

Southern Comfort

Welcome to Southern Comfort, a captivating semi-oceanfront home that invites you to experience the best of beachside living. With ocean views and convenient access to the ocean via a nearby sidewalk and pedestrian crosswalk to Ocean Blvd. beach...

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

Quack Me Up! 155-B

Looking for an affordable Duck vacation home with fantastic amenities and close to the beach access? Quack Me Up! is the place for you! A spacious and well-maintained home and has a great location within the charming Town of Duck. Sound access with...

  • Duck
  • 4 Bedrooms
  • 4.5 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...

What the Shell

This is a Blue Standard Bedding Property. Learn more about our hospitality bedding program here.Time to enjoy the best of Corolla! “What the Shell” is an adorable oceanfront house with a private pool, hot tub, and a great rec room to keep the...

  • Corolla
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 17
Donutz on a Stick

Stay, Play and Eat- Donuts, Ice Cream & Coffee Treats! Located on the Duck Boardwalk, behind Dockside Seafood, this breakfast & Dessert-Shop features treats you've never tasted before! Try the hot, made to order, donutz...

5703 - The Fritz Carlton

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! A custom home design and lavish furnishings make this home the ideal vacation destination! Relaxation awaits you in...

  • Nags Head
  • 7 Bedrooms
  • 7.5 Bathrooms
Brindley Beach Vacations

Brindley Beach Vacations offers premier Real Estate and Property Management services across the entire Outer Banks. Representing more than 450 vacation rental homes, we proudly serve every region—from the southern beaches of Hatteras Island...

La Serena

Located in Corolla / 6 Bedrooms / 5 Full Bathrooms/ 1 Half BathroomLa Serena, named after a resort north of Santiago, Chile, this home is on the high side of luxury and is "the serene one." Private Oceanfront pool and private boardwalk walkway to...

  • Corolla
  • 6 Bedrooms
  • 5 Bathrooms
Nor'Banks Sailing & Watersports

Nor'Banks Sailing & Watersports beautiful location and top-of-the-line equipment, together with a friendly and professional staff make it one of the premier water sports centers on the Outer Banks. Nor'Banks' sound front location has a huge grassy lawn, restrooms, showers, a 200 foot pier and plenty of room for you to spend the day. Since 1979 Nor'Banks has been one of the finest sailing operations on the East Coast offering Flying Scots, Hobie Cats and quality private sailing instruction...

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.