2026 Nags Head Sailing Guide

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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...

771 | Cabana

The Cabana is an exceptional Oceanfront property that provides a wide range of amenties to enhance your vacation experience. Amazing views of the Atlantic Ocean and high-end finishes are sure to please. Centrally located in Nags Head, this spacious...

  • Nags Head
  • 8 Bedrooms
  • 7.5 Bathrooms
  • Sleeps 16
The Christmas Shop

Discover gifts, garlands and glittering lights galore. Looking for a trinket for someone who has everything? Choose ornaments for every hobby, occupation, occasion or enthusiast; from the fisherman or Disney lover; dancer or photographer. Throughout...

5596 - Peak to Shore

Always Included, complimentary linens and made beds! NEW FOR 2025: New recliner and furniture. Peak to Shore is a pet-friendly Outer Banks vacation rental located in the beautiful town of Nags Head...

  • Nags Head
  • 3 Bedrooms
  • 3 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...

Windstar

Now Offering Flex Stay (3-Nighttime Minimum) for 2026!Located in Duck / 4 Bedrooms / 3 Full BathroomsAppreciate your vacation in this well-adored family bungalow located on a peaceful street on the Soundfront in the Sanderling community!  This home...

  • Duck
  • 4 Bedrooms
  • 3 Bathrooms
9/28 - 10/5
$2,595  $3,144
$549 off
Salt Coast Outfitters

We offer one of a kind SALT COAST OUTFITTERS brand name tees, long sleeves, performance gear, Yeti tumblers, caps, eyeglasses, and more! Browse the fullest collection of coastal lifestyle clothing on the beach. Featuring a sizable selection of brand...

Ohana

Exciting news—Ohana is now pet-friendly! In Hawaiian culture, 'Ohana' represents family in its broadest sense, encompassing blood relatives, adopted members, and chosen bonds. It emphasizes the importance of unity, support, and shared experiences...

  • Nags Head
  • 8 Bedrooms
  • 8 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...

Kinnakeet Retreat

OCEANFRONT Avon - Croaker Ct KINNAKEET RETREAT provides the best of both oceanfront convenience with great value! Walk directly from the home over the dune to the beach and savor a day of sun and surf. Return to a invigorating rinse int he outdoor...

  • Avon
  • 4 Bedrooms
  • 2 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...

THE CUNNINGHAM

Discover THE CUNNINGHAM in Corolla, a Carolina Designs OBX vacation rental set on Whalehead Drive just 220 yards from beach access. This spacious six-bedroom escape pairs a 28 x 16 private pool and hot tub with a rec room, sand volleyball area...

  • Corolla
  • 6 Bedrooms
  • 5.5 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...

Endeavor

SOUNDSIDE Hatteras — Hatteras Estates — When planning a beach vacation, do you include a balance of rest, relaxation, recreation, and maybe even a little personal reinvention in your future endeavors? An affirmative answer may lead you to the...

  • Hatteras
  • 3 Bedrooms
  • 2 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.