The Long Island Loop
PN152026
Newport, RI to Newport, RI
Sep 18th to September 23rd 2026
Duration 5 Days
300 Nautical Miles
Bunks Available: 2
$4,250

This round trip passage from Newport to Newport via New York City includes two overnight sails, a stop in Block Island, an offshore run to NYC, and a full East River and Hell Gate transit before returning through Long Island Sound. It is ideal for sailors looking to build offshore experience, master tidal current navigation, and practice real world seamanship along one of the busiest sailing corridors on the U.S. East Coast.
Passage summary
The Sound & City Passage
This round trip training passage begins and ends in Newport, Rhode Island, combining offshore sailing, coastal navigation, and complex tidal waterways into a single continuous loop. The route is intentionally designed to expose crew members to a wide range of real world sailing conditions while building confidence through repetition, watch standing, and hands on decision making.
Newport to Block Island
The passage begins in Newport Harbor with a crew briefing, safety orientation, and departure into Rhode Island Sound. Early miles focus on sail trim, helm balance, and crew coordination as we settle into the rhythm of the boat.
After arrival, we stop in Block Island to rest, review weather and routing, and prepare for the offshore leg ahead. Time here allows crews to reset before transitioning from coastal sailing to open water passage making.
Offshore Overnight to New York City
Departing Block Island, we sail offshore overnight toward New York City. This leg introduces structured night sailing with a three hours on, six hours off watch system. Crew members rotate through helm, lookout, and navigation duties while managing sail trim, radar, and AIS in reduced visibility.
This overnight passage is a core training component, building comfort with darkness, fatigue management, and maintaining situational awareness while underway offshore.
New York Harbor and Statue of Liberty Anchorage
Arrival into New York Harbor is timed for daylight when possible, offering clear visibility of traffic patterns and navigational complexity. After transiting the harbor, we anchor near the Statue of Liberty for an overnight stay.
This stop reinforces anchoring techniques, tidal considerations, and close quarters awareness in a busy commercial environment, while also providing a unique opportunity to experience one of the most iconic anchorages on the East Coast.
East River, Hell Gate, and Long Island Sound
From the harbor, we enter the East River and transit Hell Gate, a highlight of the passage and a critical seamanship exercise. This section emphasizes precise timing, current prediction, boat speed management, and communication as we move through strong tidal flow and confined waterways.
After clearing Hell Gate, we continue east through Long Island Sound, sailing overnight toward Newport. This final leg allows crews to apply lessons learned earlier in the passage while refining sail handling, watch routines, and navigation in mixed coastal conditions.
Return to Newport
The passage concludes with a return to Newport, completing the full loop. By this point, crew members have experienced offshore sailing, night watches, strong currents, major port traffic, and multiple anchorages, all within a single cohesive training route.




