top of page
Fort Hill - Oyster Bay Harbor Tour 1.jpg

Sightseeing Harbor Tours

Enjoy a relaxing sailing tour of historic Oyster Bay Harbor!

Oyster Bay Harbor is considered by many to be one of the most beautiful harbors on Long Island Sound making it the perfect setting for a relaxing harbor tour. You'll sail aboard WINDSWEPT, a luxurious 36' Jeanneau sailboat equipped with a large shaded cockpit for up to 6 guests. 

​​​​​

On the tour, you'll sail by:

​

  • Billy Joel's impressive former Centre Island estate, 'MiddleSea', a 20,000 sq. ft. home nestled on 26 acres of waterfront property.

  • Fort Hill, a historic 10-acre waterfront estate on Lloyd Neck built on the site of Fort Franklin, a British fort from the Revolutionary War. Originally part of a colonial manor, the site features a 37-room Tudor Revival mansion built in 1900.

  • ​​The remnants of Laurelton Hall, home of artist Louis Comfort Tiffany, son of the founder of Tiffany & Co, Charles Lewis Tiffany. The 84-room Art Nouveau mansion was situated on 600 acres before it succumbed to fire in 1957. ​

​​​

​​​​​Feel free to bring your favorite snacks and beverages to enjoy during the tour. Contact us with any special requests. We will do everything we can to create a great experience for everyone!

​​​

What's Included:

  • Licensed Captain

  • Bottled Water & Ice

  • Parking at the marina

  • Launch service to and from the boat

  • Pool floats for swimming​​

Subscribe For Updates & Promotions!

​

© 2026 Windward Sailing Charters, All Rights Reserved.

  • Instagram
  • Facebook
  • Yelp!
  • Linkedin
  • X
bottom of page