2026 Nags Head Sailing Tours Guide

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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...

Dune Diamond

Located in the heart of Nags Head, Dune Diamond is that rare gem that multi-generational families desire. Boasting beautiful views and spacious living quarters, this home provides comfort, privacy, togetherness and fun for all ages.  Spend your...

  • Nags Head
  • 8 Bedrooms
  • 9 Bathrooms
Sundogs

Sundogs is a happening spot open year round in Corolla. Along with good food, they feature a nightlife that includes Karaoke and Silent Disco! They have a full bar and a menu suited to a host of tastes. Starters include nachos, crab dip, wings and...

Out of Bounds

NEW TO BRINDLEY BEACH FOR 2026!Located in Corolla / 4 Bedrooms / 3 Full Bathrooms / 2 Half Bathrooms (1 is outside)Discover the ultimate Outer Banks experience at Out of Bounds located in the heart of the Corolla Light Community. This getaway offers...

  • Corolla
  • 4 Bedrooms
  • 3 Bathrooms
Currituck Maritime Museum

Take a day trip or an afternoon off the beach to explore the heart of Historic Corolla Park, and you’ll find one of the Outer Banks’ newest and most noteworthy attractions, the Currituck Maritime Museum.

SUNSET

Enjoy spectacular views in an intimate community of Nags Head style townhomes. Each home features 2,000 square feet of living area.Level 1:Great room with sectional sofa, CATV and DVD player; partially covered deck with ocean view; kitchen; dining...

  • Southern Shores
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 7
8/1 - 8/8
$5,394  $5,937
$543 off
9/12 - 9/19
$2,855  $2,861
$6 off
9/19 - 9/26
$2,585  $2,861
$276 off
9/26 - 10/3
$2,641  $2,861
$220 off
10/10 - 10/17
$2,634  $2,861
$227 off
10/17 - 10/24
$2,223  $2,318
$95 off
10/24 - 10/31
$2,155  $2,318
$163 off
Risky Business Shrimping and Crabbing

If you’re looking for a fun, hands-on activity that the whole family can enjoy together, hop aboard Risky Business for an Outer Banks shrimping and crabbing charter. Our experienced captain and mate will show your group how to pull crab pots...

4780 - Starfish Starlight

Always Included, complimentary linens and made beds! Located in the heart of Kitty Hawk lies Starfish Starlight, a charming beach house perfect for your next Outer Banks vacation. This delightful...

  • Kitty Hawk
  • 4 Bedrooms
  • 4 Bathrooms
Beach Realty and Construction

Over 450 Outer Banks vacation rentals with amenities such as private pools, hot tubs, elevators, keyless entry, 1 - 9 bedrooms, Oceanfront to Soundfront, 4x4 Carova...

Mystic Memories

Magnificent first class semi-oceanfront resort home in desirable South Nags Head! Professionally upgraded to include gorgeous decor, new electronics and additional amenities for your pleasure. Enjoy spectacular ocean views and stunning sunsets from...

  • Nags Head
  • 6 Bedrooms
  • 5 Bathrooms
9/6 - 9/13
$4,880  $5,380
$500 off
Bonner Bridge Pier

Opened in 2021, the Bonner Pier is one of the more unique piers along the Outer Banks, as the 1,000-ft. long concrete structure was once the southern terminal of the original Bonner Bridge. Once the bridge was replaced by the new Basnight Bridge, a...

2875 - MOJO'S

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Explore the beauty and serenity of Duck at MOJO’S! This beautiful 5-bedroom, 3-bath oceanfront Outer Banks vacation...

  • Duck
  • 5 Bedrooms
  • 5 Bathrooms
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...

OCEAN VIEW

Discover your perfect Corolla getaway at Ocean View, a spectacular semi-oceanfront retreat just steps from the sand with breathtaking views of the Atlantic. Ideal for families or large groups, this 6-bedroom home blends spacious indoor living with...

  • Corolla
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 15
2/7 - 2/14
$2,095  $2,667
$572 off
2/14 - 2/21
$2,095  $2,667
$572 off
2/21 - 2/28
$2,095  $2,667
$572 off
2/28 - 3/7
$2,095  $2,667
$572 off
3/7 - 3/14
$2,095  $2,667
$572 off
3/14 - 3/21
$2,095  $2,667
$572 off
3/21 - 3/28
$2,095  $2,667
$572 off
3/28 - 4/4
$2,392  $2,817
$425 off

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...