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. 



Afloat on Windy Lane

SOUNDFRONT Avon — Windy Ln. — Set your vacation dreams and aspirations AFLOAT ON WINDY LANE (formerly South Wind), a five-bedroom/four-full and one-half-bathroom home overlooking the Pamlico Sound, a world-class kiteboarding, windsurfing and...

  • Avon
  • 5 Bedrooms
  • 4.5 Bathrooms
Old Man Charters

  Experience the Outer Banks from the water with Old Man Charters, a personalized boat tour company based in the historic fishing village of Wanchese. Departing from a private dock on the southern end of Roanoke Island, Old Man Charters...

Sound Delight MS-847

This family-friendly four-bedroom, three and a half bathroom home in the luxurious Corolla community of Monteray Shores is just 1,069 yards from the beach! The whole family will be entertained with the private pool, hot tub, and games, as well as...

  • Corolla
  • 4 Bedrooms
  • 3.5 Bathrooms
Nags Head Dolphin Watch

Scientists run these dolphin tours as part of their research on these beloved aquatic animals, so you know this will be an interesting trip. Passengers will be able to see how researchers with the Outer Banks Center for Dolphin Research, a nonprofit...

5374 - Killin Time

MP 9. BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Killin Time is easy at this stunning Kill Devil Hills vacation home! Located in the heart of KDH, you'll be...

  • Kill Devil Hills
  • 5 Bedrooms
  • 5.5 Bathrooms
H2OBX Waterpark

YOUR BEST SUMMER DAY - Nothing satisfies your craving for fun like a day at the H2OBX Waterpark. Start with that perfect Carolina sun. Add a dose of adrenaline as you soar 6 stories up on The Rogue Wave or drop 90 screaming feet down The Plank...

BOUJEE BUNGALOW

Overview Swagger through your vacation just like you swagger through life at the Boujee Bungalow! Every detail in this 5-bedroom custom home has been carefully chosen to be the real deal. Centrally located between the ocean's edge and...

  • Duck
  • 5 Bedrooms
  • 5 Bathrooms
Fishing Unlimited Boating Center

Owned by Garry Oliver, the proprietor of the Outer Banks Fishing Pier, this small wooden aqua blue-colored store on the Nags Head-Manteo causeway has been serving the needs of fishermen for decades. A full line of tackle is available for all types...

Sun Dog

SEMI-OCEANFRONT Rodanthe - Mirlo Beach - There are bright spots all around SUN DOG! This splendid home is mins. from the sound and the many miles of secluded beaches in the Pea Island National Wildlife Refuge. There are three king master suites, two...

  • Rodanthe
  • 5 Bedrooms
  • 4.5 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...

AQUA VISTA

This stunning home has every imaginable comfort, great ocean views and easy beach access (only 30 yards from driveway). Quality is reflected throughout with hickory cabinets, granite countertops, hardwood floors, ceramic tile, and an elevator.Level...

  • Southern Shores
  • 7 Bedrooms
  • 6.5 Bathrooms
  • Sleeps 14
8/22 - 8/29
$5,829  $6,687
$858 off
9/12 - 9/19
$4,211  $4,734
$523 off
9/19 - 9/26
$4,103  $4,734
$631 off
9/26 - 10/3
$4,313  $4,734
$421 off
10/3 - 10/10
$4,313  $4,734
$421 off
10/10 - 10/17
$4,313  $4,734
$421 off
10/17 - 10/24
$3,472  $3,799
$327 off
10/24 - 10/31
$3,706  $3,799
$93 off
Jimmy's Seafood Buffet

Home of the Crab Leg & Lobster Buffet for 27 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...

083 | Blissful Breeze

2026: All new kitchen w/ new appliances, cabinets, quartz counters, tiled backsplash and island bar. Also, selected new furnishings and new large screen TV in den. Your family will love the fantastic Semi-Oceanfront location, Outstanding Ocean...

  • Kitty Hawk
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 9
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.