The Long Island Loop

New York City to New York City

Jun 26th to July 1st 2025 / Duration 5 Days

300 Nautical Miles

PN092025

$3,850

Bunks Available: 2

Passage summary

This round-trip sailing passage from Port Washington to Block Island and back via New York City offers a mix of offshore and coastal conditions. Highlights include night sailing, navigating the East River and Hell Gate, and anchoring near the Statue of Liberty. You'll gain hands-on experience with sail trim, helm work, tidal currents, radar, and AIS while exploring one of the most iconic sailing routes on the U.S. East Coast.

The Sound & City Passage

Sail through a dynamic blend of coastal cruising and urban exploration as we journey from Port Washington, NY to Block Island, with a return loop through New York City’s iconic waterways. This passage offers a rich mix of hands-on learning, night sailing, navigation through strong tidal currents, and stunning views of city skylines and quiet anchorages.

Port Washington to Block Island

Our adventure begins in the protected harbor of Port Washington on Long Island’s north shore. After a crew briefing and safety rundown, we’ll sail east into the calm but active waters of Long Island Sound, where you’ll immediately begin practicing sail trim, helm control, and tidal navigation.

As night falls, we continue offshore on our first overnight passage to Block Island. This leg introduces you to life underway with a 3-hours-on, 6-hours-off night watch rotation, helping you build confidence in low-visibility conditions while managing radar, AIS, and sail adjustments under the stars.

What You’ll Learn

Throughout the trip, you’ll gain practical offshore and coastal sailing experience, including:

Sail trim in light and shifting winds
Helm work in changing sea states
Radar and AIS navigation during night watches
Traffic and current management in high-traffic zones
Anchoring and mooring techniques
Route planning based on weather and tide
East River transit and current timing

New York Harbor & East River Transit

After time at anchor near Block Island, we sail toward New York City, entering the harbor at sunrise with unforgettable views of the Statue of Liberty and Manhattan skyline. From there, we navigate the Hudson and East Rivers, passing beneath the Brooklyn, Manhattan, and Williamsburg Bridges before reaching the intense tidal flow of Hell Gate — a true highlight for learning timing and current strategy.

As we return to Port Washington via Long Island Sound, you’ll practice sail handling in close quarters, refine boat speed and balance, and reflect on the diversity of sailing conditions experienced throughout the trip.

A Unique Coastal Journey

This round-trip passage offers a little bit of everything: offshore experience, protected sound sailing, strong currents, night watches, and one-of-a-kind views of New York City from the water. Whether you're a beginner sailor looking to grow or an experienced hand ready for a new kind of challenge, this route blends technical skill-building with unforgettable moments on deck.

Set sail with us around Long Island — experience the Sound, the city, and the sea in one immersive passage.

Sailing Weather Overview

Late June provides excellent sailing conditions around Long Island, blending warm days, stable southwest winds, and manageable sea states. This route includes both protected coastal waters and open Atlantic stretches, offering a well-rounded sailing experience with strategic considerations for tidal currents and wind shifts near headlands.

Temperatures

Air temperatures range from 75–85°F (24–29°C) in Long Island Sound to 85–90°F (29–32°C) near New York City, with nighttime lows around 65–70°F (18–21°C). Water temperatures vary by region: 65–70°F in the Sound, 68–74°F along the Atlantic coast, and 60–65°F in New York Harbor.

Sailing Strategy

We should expect southwest winds between 10–20 knots, strongest in the afternoons. In Long Island Sound, light to moderate breezes favor comfortable beam or close-reaching. On the Atlantic side, conditions support broad reaching, especially on clockwise routes. Near New York Harbor, gusty and channeling winds may require motoring or frequent course adjustments, particularly when transiting the East River or Hell Gate.

Travel & Logistics

All passages are weather-dependent, and timing of departure or arrival may shift slightly based on conditions. You’ll board Libra in Port Washington, New York, a well-protected harbor with easy access to Long Island Sound. Arrival is scheduled for the afternoon of June 24th, with final details and dock location provided prior to departure.

Closest Airports:

- LaGuardia Airport (LGA) – 30 to 45 minutes by car or public transit
- John F. Kennedy International Airport (JFK) – 45 minutes by car
- Newark Liberty International Airport (EWR) – Approximately 1 hour by car or train

Public transit options are available via LIRR (Long Island Rail Road) to Port Washington station, just a short ride from the dock.

Disembarkation will take place in Port Washington on or after June 30th, depending on the final route and weather window. If sailing a counterclockwise route, final night anchorage may be near the Statue of Liberty, with return up the East River the following day.

A valid government-issued ID is required for travel within the U.S.

No passport is needed for this domestic coastal passage.

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