2026 Nags Head Sailing Tours Guide

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Twiddy & Company

Twiddy & Company is here to provide all the help and southern hospitality you've come to anticipate when planning your beach vacation. We invite you to let us share our unique understanding of this coastal landscape; unlike any place in the...

Sea Castle

OCEANFRONT Waves - Mac-Oca Dr. Savor the island lifestyle and a touch of the royal treatment with a stay at decadent SEA CASTLE. This towering oceanfront palace offers front row vistas from multiple levels of decks, and regal amenities around every...

  • Waves
  • 5 Bedrooms
  • 5.5 Bathrooms
Gray's

Gray’s Outer Banks Lifestyle Clothing Company offers the absolute best in Outer Banks T-shirts and Sweatshirts including Champion, Under Armour with "Outer Banks” and Gear! We carry quality fashions and accessories for the whole family...

BOBBIS BUNGALOW

“Bobbi’s Bungalow” is tucked away in a small Oceanfront community with a community pool and tennis court. Fun attractions, shopping and great restaurants are only a short walk away! This beautiful duplex will give you the perfect backdrop to a...

  • Nags Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
3/21 - 3/28
$2,233  $2,576
$343 off
3/28 - 4/4
$2,482  $2,726
$244 off
4/4 - 4/11
$2,612  $2,726
$114 off
4/11 - 4/18
$2,612  $2,726
$114 off
4/18 - 4/25
$2,449  $2,726
$277 off
4/25 - 5/2
$2,384  $2,726
$342 off
5/2 - 5/9
$2,538  $2,907
$369 off
5/9 - 5/16
$2,538  $2,907
$369 off
5/30 - 6/6
$4,482  $4,846
$364 off
6/20 - 6/27
$5,800  $6,077
$277 off
6/27 - 7/4
$6,280  $6,693
$413 off
Cosmo's Pizzeria Southern Shores

If you're searching for great pizza on the Outer Banks, look no further than Cosmo's Pizzeria at The Marketplace in Southern Shores! We offer authentic New York-style pizza made fresh and just the way you like, using only the highest quality...

On Island Time

Located in Corolla/ 8 Bedrooms/ 6 Full Bathrooms/ 1 Half Bathroom"On Island Time" is your summertime hideaway!! Savor the days of summer in this "get-away-from-it-all" beach home. To ease you into a calming vacation, this huge semi-oceanfront home...

  • Corolla
  • 8 Bedrooms
  • 6 Bathrooms
Moge Tee

QUALITY YOU CAN SEE, FRESHNESS YOU CAN TASTE! Every cup made to order with the freshest ingredients and handcrafted loose leaf tea brewed to perfection! Combining all the natural gifts from mother nature!

Sunset II Sea 158-F

Spectacular sunsets await you at Sunset II Sea, an oceanside home with unobstructed soundfront views from almost every room and all decks! Enjoy relaxing in your own private saltwater pool and hot tub when you're not spending time on the beach...

  • Duck
  • 7 Bedrooms
  • 6.5 Bathrooms
ZoomAround Street Legal Golf Cart Rentals

ZoomAround Street Legal Golf Cart Rentals provides our communities and our visitors with fun, safe and convenient access to innovative transportation while providing an unparalleled customer experience. Don’t carry all of your beach gear...

Celtic Tides

Located in Corolla / 6 Bedrooms / 6 Full Bathrooms / 1 Half BathroomPacked with amenities, your family will appreciate this unique vacation home in the Corolla Light Resort Community. Offering a enormous pool that will accommodate the whole family...

  • Corolla
  • 6 Bedrooms
  • 6 Bathrooms
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...

The Nags Header

The Nags Header was named after the famous ‘Nags Header’, a gathering place from simpler times on the Outer Banks. This Victorian Style vacation home will to take you to quieter, simpler days. Enjoy the sunrise from the large deck or take a dip...

  • Nags Head
  • 7 Bedrooms
  • 9 Bathrooms
Basnight's Lone Cedar Cafe

Enjoy Waterfront Dining at Basnight's Lone Cedar Café where we specialize in fresh and local Outer Banks seafood. If you’re craving the freshest fish, clams, crab, shrimp and oysters from local North Carolina waters, you’ll find...

4218 - The Scotts' SandBar

Always Included, complimentary linens and made beds! NEW FOR 2026: Living room furniture and updated outdoor shower. Welcome to The Scotts’ SandBar! This Georgetown Sands condo has everything you...

  • Duck
  • 2 Bedrooms
  • 2.5 Bathrooms

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...