2026 Sailing Tours Guide

Outer Banks Map
Carova Corolla Duck Southern Shores Kitty Hawk Kill Devil Hills Manteo Nags Head Wanchese Rodanthe Waves Salvo Avon Buxton Frisco Hatteras Ocracoke
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Sun Realty

Sun Realty offers the Best Selection of Vacation Rentals on the Outer Banks. Our large selection of Outer Banks rentals means you can choose from a wide range of amenities, including private swimming pools, hot tubs, theater rooms, game rooms, pet...

LIVE OAK LANDING

Live Oak Landing offers a private retreat for your family’s perfect beach vacation. An easy 450 yard walk to the community beach access. Then, return to your own pool, hot tub, game room, and space for everyone. Memories are made here.Level 1:2...

  • Southern Shores
  • 5 Bedrooms
  • 3.5 Bathrooms
  • Sleeps 10
7/3 - 7/10
$3,926  $4,302
$376 off
7/17 - 7/24
$3,926  $4,302
$376 off
7/24 - 7/31
$3,926  $4,302
$376 off
8/14 - 8/21
$3,040  $3,172
$132 off
8/21 - 8/28
$2,774  $2,984
$210 off
8/28 - 9/4
$2,370  $2,607
$237 off
9/4 - 9/11
$2,246  $2,419
$173 off
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...

Diamond Dunes DSB-103

Enjoy oceanfront living along the beautiful beaches of South Nags Head at Diamond Dunes!Located just 50 feet from the beach, Diamond Dunes is a modern, single-level 1st level unit within the Diamond Shoals Condominiums, located at milepost 17. The...

  • Nags Head
  • 3 Bedrooms
  • 2 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...

THE DAPPER DUCK

The Dapper Duck is a four bedroom OBX vacation rental in Southern Shores. Located just 200 yards from beach access, this home features a wood fireplace and gorgeous horizon ocean views from the upper deck. Its convenient location means that it’s...

  • Southern Shores
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
7/12 - 7/19
$2,204  $2,503
$299 off
7/26 - 8/2
$2,204  $2,503
$299 off
8/2 - 8/9
$2,204  $2,503
$299 off
8/9 - 8/16
$1,896  $2,141
$245 off
8/16 - 8/23
$1,835  $2,068
$233 off
8/23 - 8/30
$1,711  $1,923
$212 off
8/30 - 9/6
$1,490  $1,662
$172 off
9/6 - 9/13
$1,410  $1,568
$158 off
9/13 - 9/20
$1,251  $1,398
$147 off
9/20 - 9/27
$1,251  $1,398
$147 off
9/27 - 10/4
$1,251  $1,398
$147 off
10/4 - 10/11
$1,265  $1,398
$133 off
10/11 - 10/18
$1,300  $1,398
$98 off
10/18 - 10/25
$1,195  $1,216
$21 off
10/25 - 11/1
$1,195  $1,216
$21 off
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...

No Ragrets 52-C

No Ragrets is a bright and airy beach house, located only 75 feet to the beach access, with beautiful ocean views and one of the largest private pools (14x25) in the popular Corolla community of Ocean Sands. Before heading out to the beach each day...

  • Corolla
  • 4 Bedrooms
  • 3 Bathrooms
Flip Flop Shops

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



The Dune Bug

Welcome to your serene escape in Nags Head! Our charming Oceanside cottage, nestled just one house back from the beach and a mere 150 feet from beach access, offers a peaceful haven for couples or small families. Imagine waking up to the sound of...

  • Nags Head
  • 2 Bedrooms
  • 1 Bathrooms
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...

7045 - Seabreeze

Always Included, complimentary linens and made beds! New for 2024: Updated Kitchen Appliances, Updated 3rd Level Shower, Updated 2nd Level Bathtub. Welcome to Seabreeze, your dream OBX vacation...

  • Rodanthe
  • 6 Bedrooms
  • 6 Bathrooms
Firehouse Boil Delivery

DIY Seafood Boil Don’t Just Make Dinner, Make An Experience! We Deliver on the Outer Banks! Same Day Delivery! Make lasting memories by doing something new with friends and family. Why wait in line at a grocery store or restaurant? Our Low...

Sea Isle

Located in Waves | 7 Bedrooms | 6 Full Bathrooms | 1 Half BathroomAfter a striking beach day on the ocean or spending time up at the Pea Island wildlife sanctuary, offering the most spectacular vistas and best secret marsh fishing, come home and...

  • Waves
  • 7 Bedrooms
  • 6 Bathrooms
9/29 - 10/6
$1,996  $2,496
$500 off
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.

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...