Explore the Best of Coastal New England

 

Join us for a spectacular coastal sailing adventure from New York City to Newport, Rhode Island aboard Sail Libra. This multi-day passage combines the excitement of offshore and coastal cruising with the charm of some of New England’s most scenic anchorages. You’ll experience the thrill of navigating New York Harbor, an exhilarating overnight offshore leg, and the peaceful beauty of Block Island and the Elizabeth Islands before arriving in the sailing capital of the U.S. — Newport.

This trip is ideal for both experienced sailors looking to refine their skills and adventure seekers eager to discover the true cruiser lifestyle. Along the way, you’ll build confidence in offshore conditions, sharpen your navigation skills, and immerse yourself in the rhythm of life at sea.

 

New York City to Block Island — Urban Skyline to Open Ocean

Our adventure begins in Port Washington, where we’ll prepare Libra for the passage and get the crew familiar with the boat and each other. After a safety briefing and provisioning check, we’ll cast off and head south toward New York City. We’ll navigate through the busy and iconic waters of New York Harbor — passing beneath the towering spans of the:

 

• Verrazzano Bridge
• Brooklyn Bridge
• Manhattan Bridge
• Williamsburg Bridge
• Queensboro (59th Street) Bridge
• RFK (Triborough) Bridge
• Whitestone Bridge
• Throgs Neck Bridge

 

Overnight Sail into the Atlantic

Once clear of the harbor, we’ll set a course for Block Island, heading out into the open Atlantic for an exhilarating overnight passage. This leg will provide a true offshore experience, where you’ll settle into the rhythm of life at sea under a rotating 3 hours on, 6 hours off watch schedule. During the night sail, you’ll have the chance to practice:

 

• Night navigation – Relying on radar, AIS, and GPS.
• Helm time – Maintaining a steady course under starry skies.
• Sail handling – Adjusting sail trim for offshore swells and changing wind patterns.
• Traffic awareness – Monitoring shipping lanes and commercial traffic along the Atlantic coast.

 

Port Judith or the Elizabeth Islands to Newport — The Final Stretch

From our final anchorage, we’ll set a course toward Newport, Rhode Island — one of the most famous sailing capitals in the world. This leg will provide a mix of coastal and harbor navigation, including:

 

• Fine‑tuning sail trim for changing wind conditions.
• Working tidal currents to optimize boat speed.
• Helm time — Taking charge and holding course in busy waters.

 

Why This Passage is Special

A Mix of Offshore and Coastal Sailing – From the calm waters of Long Island Sound to the rolling Atlantic swells, this trip offers the best of both worlds.

 

• New York City by Water – Sail beneath iconic bridges and experience the urban energy from a unique perspective.
• World‑Class Destination – Newport’s rich sailing history and lively waterfront make it the ultimate arrival point.
• Hands‑On Learning – Captain Ryan’s relaxed but professional teaching style ensures that sailors of all levels feel confident and engaged.

 

Life on Board Libra

This trip isn’t just about learning — it’s about experiencing life on a working sailboat. Days will be structured around our 3‑on, 6‑off watch rotation, giving you time at the helm, trimming sails, and handling lines. You’ll work alongside your fellow crew members as part of a team — balancing moments of quiet with the shared experience of offshore sailing.

 

While offshore, meals are prepared onboard by Libra's mate using simple but hearty ingredients including meat (veg always an option) — think pasta, fresh salads, and snacks to keep your energy up. When we're at anchor, there’s usually time to relax and unwind.  You will NEVER be hungry aboard Libra.