2026 Nags Head Sailing Tours Guide

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Outer Banks Blue

Since 2005, Outer Banks Blue has delivered exceptional vacations for OBX visitors. Our family-owned and locally managed rental company focuses on service and promises “a relaxing experience with a local touch.” Turn your dream vacation...

Thor at the Shore VICT-5

This oceanfront family-friendly Nags Head cottage has everything you need for a fun and relaxing Outer Banks vacation. Wake up early to watch the beach waves and sunrise from your oceanfront deck. Just steps away, across the private Viking Court...

  • Nags Head
  • 5 Bedrooms
  • 2.5 Bathrooms
10/3 - 10/10
$2,573  $3,273
$700 off
10/10 - 10/17
$2,669  $3,369
$700 off
10/17 - 10/24
$2,549  $3,249
$700 off
10/24 - 10/31
$2,487  $3,187
$700 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...

1538 - Gift Of The Sound

Always Included, complimentary linens and made beds! FOR 2026: Pool will open May 16, 2026. You’ll see never-ending sound and sunset views from this beautifully designed and furnished home in...

  • Corolla
  • 5 Bedrooms
  • 5 Bathrooms
Big Buck's Homemade Ice Cream

Serving our customers on the Outer Banks since 1994, Big Buck's ice Cream is dedicated serving you “The Best.” We offer a full line of super-premium ice cream products, smoothies, chocolates, and custom-made ice cream cakes! 2 locations...

5544 - Carolina Surf

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Carolina Surf is a stunning newly built "coastal cottage" which is located at MP 14 in the Moongate subdivision of The...

  • Nags Head
  • 6 Bedrooms
  • 7 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...

Island Tempest

SOUNDFRONT Avon - Island Creek Dr. – The sky is blue, the water is warm, and a gentle breeze of 15 knots is blowing cross onshore winds. What could be more ideal for the avid wind and kite surfer? For those who adore and live for the water, it...

  • Avon
  • 3 Bedrooms
  • 3.5 Bathrooms
Poke Box

PokeBox offers fresh, quick, simple, healthy poke bowls in Nags Head. Choose your items and build your bowl. Tuna, salmon, chicken, steak, shrimp and tofu options available. Mix in your favorite veggies, sauces and toppings for the perfect poke...

Tranquil Waves

OCEANFRONT Waves - Sea Vista Dr. - Let TRANQUIL WAVES sweep your worries away and dive into effortless vacation bliss! This five-bedroom, three-and-a-half-bath heaven is your ticket to relaxation, entertainment, and a treasure trove of memories...

  • Waves
  • 5 Bedrooms
  • 3.5 Bathrooms
Miller's Waterfront Restaurant

MILLER’S OFFERS ONE OF THE FEW TRULY WATERFRONT DINING EXPERIENCES ON THE OUTER BANKS. Enjoy casual dining in our downstairs family-friendly seafood restaurant, or our signature drinks and grill menu in our upstairs deck bar while watching...

Point of View

Located in Corolla/ 4 Bedrooms/ 2 Full Bathrooms/ 1 Half BathroomYour family will adore this Whalehead home located close to eateries, stores and the Coral Street beach Access! Appreciate roomy furnished decks and ocean vistas from this 6th row...

  • Corolla
  • 4 Bedrooms
  • 2 Bathrooms
Joe Lamb Jr. & Associates

Since 1968, our family owned and operated company has offered families just like yours a wide selection of Outer Banks vacation rentals in beach communities and towns of Duck, Southern Shores, Kitty Hawk, Kill Devil Hills, Nags Head and South Nags...

Bailey's Irish Dream

Dreams do come true at “Bailey’s Irish Dream” in Nags Head! This is a great spot for family vacations close to the beach, with a pool and hot tub! Make precious memories with your loved ones at the beach while spending time in this fabulous...

  • Nags Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
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.