2026 Nags Head Sailing Tours Guide

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Resort Realty Property Management

Celebrating 39 years of service in Outer Banks vacation rental property management, Resort Realty is a company that operates locally with in-house feet on the ground; meaning impeccable care for your home with constant communication from our staff...

THE PORTER HOUSE

With 3,000 square feet of open and airy design, The Porter House offers a refreshing retreat in the heart of Duck. Enjoy easy access to shops, restaurants, and the beach, all within a short walk.Level 1:1 bedroom with Pyramid bunk. Game room with...

  • Duck
  • 6 Bedrooms
  • 6.5 Bathrooms
  • Sleeps 12
5/30 - 6/6
$4,060  $4,674
$614 off
8/29 - 9/5
$3,806  $4,065
$259 off
9/5 - 9/12
$3,628  $3,718
$90 off
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...

R-10 | The Regency Condominium

Breathtaking Ocean Views await from this lovely, top-floor oceanfront condominium unit located at the Regency in Kill Devil Hills. All will enjoy the fantastic beach front location and the luxury of having a swimming pool on-site. Beautifully...

  • Kill Devil Hills
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Brew Thru

No trip to the Outer Banks is complete without cruising through Brew Thru, the Outer Banks’ original drive thru convenience store. Whether you’re looking for a refreshing cold beverage of Coke, Pepsi and other soft drinks on the go...

PENN STATION

A family favorite! Spacious and beautifully decorated, Penn Station offers the comforts and amenities of home. 2,950 square feet of living area and 1,900 square feet of decks provide ample room to relax and enjoy a carefree vacation in a lovely...

  • Southern Shores
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
5/31 - 6/7
$2,985  $3,410
$425 off
Jimmy's Seafood Buffet

Home of the Crab Leg & Lobster Buffet for 26! 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...

PAPAS LEGACY

Experience the simplicity of the 1950's-built lower level of this sunshine yellow beach house, once known as a flattop bungalow, with its gorgeous Juniper woodwork throughout. Enjoy the soothing ocean breezes on the original wraparound lower level...

  • Southern Shores
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
8/22 - 8/29
$3,769  $4,013
$244 off
Paradise Fun Park

Off the beach, one of the best activities for groups to enjoy in the Outer Banks is mini golf, bumper cars or Go-Karts. Thankfully, Paradise Fun Park offers all three activities! Paradise Fun Park offers exciting outdoor activities that kids and...

Ocean Oasis

Paradise on the OBX! That’s what describes this lovely beach cottage in South Nags Head, just waiting for you and your family to enjoy! There are fabulous views of the ocean from the decks, Great Room, dining area, or kitchen. The top-level deck...

  • Nags Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
American Pie

Discover the best homemade ice cream and authentic made-from-scratch New York Style pizza the Outer Banks has to offer at American Pie in Kill Devil Hills. An Outer Banks favorite for lunch, dinner or a delicious scoop of scrumptious ice cream after...

Catching Rays

Judge’s Choice Award for the 2016 Parade of Homes.Come to Catching Rays, and you’ll forget to count the days.Begin a new tradition at Catching Rays, a magnificent cedar shake beach property in Kill Devil Hills. Inside and out, this spacious...

  • Kill Devil Hills
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Southern Shores Realty

Southern Shores Realty offers over 350 Outer Banks rentals from Corolla to S. Nags Head.  We've been an Outer Banks tradition since 1947, providing families just like yours with memories that last a lifetime.  Take a moment to search...

452 | Beach Runner

Nicely decorated, comfortable, and well-maintained, Beach Runner cottage is a short walk to the Beach Access (direct access to Admiral Street Beach Access) and a short walk to the local grocery store. The home is well equipped w/TV's in each...

  • Nags Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6

Kitty Hawk Kites’ Whalebone Watersports Center is your one-stop shop for Outer Banks water adventures. Located on the Nags Head-Manteo Causeway right on Roanoke Sound, this location offers it all – dolphin watching cruises with a marine...