A Newport-to-Newport Adventure

 

THIS PASSAGE HAS 2 OVERNIGHT SAILS

 

Experience the best of Long Island by sea as we set sail from Newport, Rhode Island, and circumnavigate the iconic Long Island on a passage that blends offshore challenge with inshore exploration. Over the course of this round-trip journey, we’ll complete two overnight sails, anchor at Block Island and New York City, and navigate the ever-shifting currents of Long Island Sound.

 

This looped route is ideal for sailors eager to grow their confidence, gain bluewater experience, and see one of the East Coast’s most iconic cruising grounds from every angle — all in one trip.

 

 

Newport to Block Island — Settling In and First Night Sail

 

We’ll begin our adventure in Newport, with time to prepare the boat and get to know your fellow crew. After a safety briefing and sail check, we’ll set off into Rhode Island Sound and head for Block Island.

 

This leg introduces you to offshore conditions and includes:

 

• Watch rotation practice (3 hours on, 6 off)
• Helm time and sail trim
• Anchoring in Block Island’s Great Salt Pond

 

 

Offshore to NYC — Into the Atlantic and the Hudson

 

From Block Island, we head south and west into the Atlantic for an exhilarating overnight sail toward New York City. This is a true offshore leg, with the open Atlantic on one side and the glowing NYC skyline on the other. Expect full night watch rotations and hands-on offshore experience.

 

We’ll likely anchor near the Statue of Liberty or moor at a nearby marina, giving you a front-row seat to the city from the water.

 

 

The East River and Long Island Sound — Riding the Currents

 

Leaving New York Harbor, we’ll ride the East River through Hell Gate, navigating tight tidal windows and strong currents. The energy of the city gives way to the more protected waters of Long Island Sound, where we’ll enjoy a different kind of challenge — sail trim finesse, local traffic management, and navigation around headlands, islands and Lighthouses.

 

 

Return to Newport — Final Night Sail and Coastal Finish

 

Our final leg takes us into the Sound for one last overnight sail, passing Montauk and re-entering Rhode Island Sound for a return to Newport.

 

Expect an engaging combination of:

 

• Traffic Management
• Night helm time and route adjustments
• Watchstanding in offshore and coastal conditions
• We’ll arrive back in Newport with a complete loop of Long Island under our keel on entered into your logbook.

 

 

Why This Passage is Special

 

• A Full Circumnavigation by Sea – Complete the loop around Long Island with two night sails and multiple anchorages
• Iconic Sights from the Water – Explore Block Island, Sail beneath NYC’s bridges (8 out of 9), and anchor by Lady Liberty. 
• Diverse Sailing Conditions – Offshore challenge, inshore navigation, strong currents, and quiet anchorages
• Hands-On Experience – Ideal for building confidence in both offshore and coastal cruising environments

 

 

Life on Board Libra

 

You’ll sail as an active part of the crew under our standard 3-on, 6-off watch system during overnight legs. Days are balanced between focused sailing and anchorage time. You'll rotate through all aspects of sailing — helming, navigating, sail trim, lookout, anchoring, and galley duty.

 

Meals aboard are wholesome and satisfying: pastas, fresh salads, grain bowls, and more — always with vegetarian options. Whether it’s coffee at dawn or a warm meal after a night shift, the crew keeps everyone fueled and connected.