2026 Nags Head Sailing Tours Guide

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Jolly Roger

When you first catch sight of The Jolly Roger, you might be unsure exactly what to think of it. Since its conversion from a gas station/grocery store to a restaurant in 1972, The Jolly Roger has been anything but your ordinary Outer Banks...

1265 - Sea Pappy's

BEACH GEAR RENTAL INCLUDED! Always Included, complimentary linens and made beds! Quaint, cozy, and perfect for your next OBX vacation is Sea Pappy's! Located in The Beach Club at Whalehead, this 2...

  • Corolla
  • 2 Bedrooms
  • 2 Bathrooms
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...

Osprey

Located in Avon / 6 Bedrooms / 4 Full BathroomsOsprey is a unique oceanfront home centrally located in Avon Village with the beach as its backyard! Your options don't end at the beach... savor the 8-person hot tub or appreciate over 2,000 square...

  • Avon
  • 6 Bedrooms
  • 4 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...

VH120 Just Enough at Villas of Hatteras ...

Welcome to Just Enough at Villas of Hatteras Landing by KEES Vacations! Rarely do getaways have a smaller getaway built into them, but that's exactly what you will find at Hatteras. While the Outer Banks is a place overflowing with culture and...

  • Hatteras
  • 1 Bedrooms
  • 1 Bathrooms
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...

Dolphin Watch

Located in Corolla / 4 Bedrooms / 2 Full BathroomsAccessible by 4x4 car only! Dolphin Watch is charmingly located just 3 1/2 miles from the end of the paved road in the Swan Beach area. You will savor unobstructed ocean vistas from both levels...

  • Corolla
  • 4 Bedrooms
  • 2 Bathrooms
Kitty Hawk Surf Co.

Experience more adventure, fun, and style with Kitty Hawk Surf Company. As the trusted Outer Banks retailer for all top surf and lifestyle brands, including, Hurley, Billabong, RVCA, The North Face, Patagonia, Salt Life, Salty Crew, Volcom...

6284 - Barker's Jewel

BEACH GEAR RENTAL INCLUDED!  Always Included, complimentary linens and made beds! New for 2025: Renovated Kitchen and New Appliances, New West-Facing Decking with Polywood Furniture, New LVP...

  • Nags Head
  • 4 Bedrooms
  • 4 Bathrooms
Fishing Unlimited Boating Center

Owned by Garry Oliver, the proprietor of the Outer Banks Fishing Pier, this small wooden aqua blue-colored store on the Nags Head-Manteo causeway has been serving the needs of fishermen for decades. A full line of tackle is available for all types...

1767 - Fox Snooze

Always Included, complimentary linens and made beds! New in 2024: Sunday Check-In.  If you're looking for an Outer Banks getaway, look no further than this 4 bedroom, 4.5 bathroom Corolla vacation...

  • Corolla
  • 4 Bedrooms
  • 4.5 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...

Dixie Sandcastle

Now Offering Flex Stay (3-nighttime minimum) Beginning September 1. Located in Corolla / 6 Bedrooms / 4 Full Bathrooms / 2 Half Bathrooms (1 Outside by private pool)Accessible by 4 x 4 car only! Welcome to Dixie Sandcastle where you will savor...

  • Corolla
  • 7 Bedrooms
  • 4 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.