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Long distance sailing and island exploring

Scroll down for passage info, dates and pricing

About Sail Libra

At Sail Libra, we're passionate about providing adventurers like you with an unforgettable sailing experience. With decades of navigating the open seas, our crew is dedicated to delivering safe and immersive passages that go beyond the basics of sail training.

Experience the Difference

Our around Long Island training trips specialize in cruiser training, offering hands-on experience and real-world navigation skills that prepare you for the challenges of long-distance sailing. Unlike traditional sail training programs, we focus on practical skills like night sailing, utilizing the environment for safe navigation, and making sound decisions in varying weather conditions.

Explore Long Island Like Never Before

Join us on a five-day circumnavigation of Long Island, NY, and embark on an exhilarating journey through the Atlantic Ocean and New York's historic waterways. From navigating under iconic bridges to experiencing the tranquility of the open sea and Long Island Sound, our trips offer a unique perspective on coastal and offshore cruising.

Meet Our Crew

Led by experienced sailors and certified instructors, our crew is dedicated to ensuring your safety and enjoyment throughout the journey. With a passion for sailing and a commitment to excellence, we're here to help you learn, explore, and create memories that will last a lifetime. read about us here


Training Trip Details

Ready to embark on the adventure of a lifetime? Our five-day training trips are designed to provide you with an immersive and educational experience that goes beyond traditional sail training. Here's what you can expect:

Comprehensive Itinerary

Our training trips start and end in Newport, RI, or a similar location along the Connecticut coastline. From there, we'll set sail on a journey around Long Island, NY, following a carefully planned route that highlights the best of the region's coastal beauty and maritime heritage, clockwise or counter clockwise as the weather dictates.  Stops in Block Island and NYC area are a must on this trip, we may have time to anchor in a 3rd location along the way for lunch or dinner.  Stops are always based on weather and safety.

Hands-On Learning

At Sail Libra, we believe in learning by doing. Throughout the trip, you'll have the opportunity to practice essential sailing skills, including sail trim, navigation, and maneuvering in various weather conditions. Our experienced instructors will guide you every step of the way, ensuring you gain confidence and competence on the water.

Real-World Navigation

Experience the thrill of navigating by the stars and utilizing the environment to make informed decisions about route planning and timing. Whether it's charting a course through busy shipping lanes or anchoring in a secluded cove, you'll learn the skills needed to navigate safely and confidently in some of Americas busiest waterways


Participant Experience

Don't Just Take Our Word for It

Curious about what it's like to sail with Sail Libra? Hear from some of our past participants:

"The experience of night sailing was incredible! Navigating under the stars with the guidance of the crew was both exhilarating and educational." - John, Kansas

"Living underway allowed me to fully immerse myself in the sailing lifestyle. From sunrise to sunset, every moment felt like an adventure. This was my first overnight boating experience" - Sarah, Massachusetts

"As someone new to long-distance sailing, I was nervous at first, but the crew made me feel right at home. Their patience and encouragement helped me gain confidence on the water." - Emily, Rhode Island

"The circumnavigation of Long Island was an unforgettable journey filled with breathtaking views and unforgettable moments. I highly recommend Sail Libra to anyone looking for a true sailing adventure." - David, Michigan

"I've been sailing for years, but Sail Libra's training trip took my navigation confidence to the next level. From navigation techniques to hands-on sail handling, I walked away feeling like a more confident sailor ready to get out there again on my own boat." - Robert, New York

Past trips around Long Island

Take a glimpse into life aboard our custom-designed Ketch with photos and videos from past training trips. From breathtaking sunsets to lively onboard discussions, the memories made on our journeys are truly unforgettable.



Limited Time Offer & Dates

Below are the dates and pricing for each Long Island Sound training trip  Availability listed here is subject to change, if you have questions about a specific date please let us know you can also view all of our passages for 2024 here and 2025 here

PASSAGE 13: AUGUST 1 - 7 | 6 DAYS | 350+NM
Cost Per Bunk $3250

PASSAGE 14: AUGUST 15 - 21 | 6 DAYS | 350+NM

Cost Per Bunk $3250

PASSAGE 15: SEPTEMBER 7 - 14 | 7 DAYS | 350+NM

Cost Per Bunk $3725


Cost Per Bunk $3250

AND SAVE 10% Off
These Published Rates

Why Wait?

With our discounted offer (very rare), there's never been a better time to embark on a sailing journey with Sail Libra. Whether you're planning a solo adventure or bringing a friend, take advantage of this special deal and make memories that will last a lifetime.

Have questions?contact us here, or send us an email to

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