Private Sailing Lessons on Long Island’s North Fork | SailSelinaNY
Quick Details
Greenport Village & Shelter Island – Dering Harbor
⛵ Departure Locations
Up to 6 guests — private and extra-personal
👥 Group Size
Total beginners to intermediate sailors welcome
🎓 Skill Levels
🌊 Waters Sailed
Peconic Bay & Shelter Island Sound — calm & scenic
Hands-on learning aboard a historic wooden yacht
✨ Instruction Style
Helm control, sail trim, navigation & seamanship basics
📖 Topics Covered
Expert captain + friendly crew coaching every step
👩✈️ Instructor
Bring your favorite North Fork wine or bubbly to celebrate
🍷 BYOB
Expect coastal wildlife, lighthouse views & open horizons
🐬 Local Beauty
👶 Family Friendly
Kids encouraged; life jackets for all ages
🅿 Parking
Convenient access near departure marinas
📅 Season
May–October — weekends book fastest
Pair your lesson with nearby wineries & waterfront dining
🔗 Plan the Perfect Day
Couples, families, adventure-seekers & future sailors
💙 Ideal For
A scenic ferry ride away — a unique boating experience near the South Fork
📍 Close to Hamptons
Private Sailing Lessons on a Classic 1926 Wooden Yacht
Learn to Sail on Long Island’s East End. Step aboard SailSelinaNY for private sailing lessons Long Island NY. Built in Greenport in 1926, this classic yacht. offers an authentic way to learn to sail in Greenport, NY, and explore Shelter Island Sound.
Whether you’re brand‑new or seeking beginner sailing lessons Long Island, our captain and crew provide expert, patient instruction.
North Fork lessons are intimate, immersive, and designed for small groups, our private sailing instructions on Long Island are limited to just six guests.
What You’ll Learn in Your Private Sailing Lesson
Your captain will guide you through every step of the sailing process in a relaxed, confidence-building atmosphere:
How to take the helm and steer under sail
Raising and trimming the sails for speed and balance
Reading wind direction and the four points of sail
Sail controls and the physics of sailing
Line handling, docking, and navigation fundamentals
Knots, weather, and Rules of the Road
Safety, communication, and seamanship etiquette
👉 In just two hours, you’ll get a foundation that many sailors take months to learn—yet you’ll walk away knowing you’ve only scratched the surface.
Because Selina is a historic wooden yacht, the lesson is unlike contemporary sailing instruction. This is classic sailing at its purest—single sail, gaff rig, beautiful varnished wood, and a boat that responds directly to your touch on the helm.
Unlike typical sailing schools, this is classic yacht sailing lessons at their purest. With a gaff rig and 1,000 sq. ft. mainsail, you’ll feel the direct response of a historic catboat. It’s not just instruction. It’s heritage, craftsmanship, and adventure all in one.
Lessons are available for groups from 1 to 6. No experience required.
Why Learn to Sail on SailSelinaNY
Who This Sailing Lesson Experience Is For
First-time sailors
Couples looking for a unique adventure
Families and small groups
Visitors and locals who want a hands-on boating experience
Experienced sailors curious about gaff rig and classic yacht handling
Anyone who wants a private, welcoming, no-pressure environment
If you’ve ever dreamed of sailing a true classic, this is your moment.
Your Sailing Lesson Itinerary
1. Welcome Aboard
Meet your captain and crew, get oriented to the yacht, and learn the plan for the lesson.
2. Safety + Seamanship Basics
Wind direction, sail controls, and onboard communication.
3. Raise the Sail
You’ll participate in the hands-on process of getting the boat underway.
4. Take the Helm
Steer across the waters of Peconic Bay and Shelter Island Sound.
5. Learn Sail Handling
Trim, tack, practice turns, and understand how to move with the wind.
6. Docking + Wrap-Up
Return to the dock with new knowledge, confidence, and skills.
Sailing Lesson Guest Reviews
★ ★ ★ ★ ★
“The lesson was inspiring and hands-on. The captain and crew were patient and made us feel confident at the helm.”
— tonia-ross5
“Tailored to our skill level, relaxed, and fun. We felt confident sailing afterward. Highly recommended!”
— Lis B
What Else to Expect from your East End Sailing Lesson
A Classic Yacht
Learn aboard an impeccably maintained wooden catboat—mahogany trim, polished brass, and timeless heritage.
Friendly, Expert Instruction
Captain Luna and crew teach with patience, clarity, and a passion for classic sailing. Your success and comfort are the focus.
Calm, Scenic Waters
Sail through the waters on the East End of Long Island. The peaceful rhythm of the waves and the breeze in the sails make learning both calming and empowering. Located on the North Fork, we are only a ferry boat ride away from the South Fork and the Hamptons. Join us for your sailing adventure and book your private sailing lesson today — your adventure starts at the helm!