New York City

Live aboard Boundless for seven unforgettable days of sailing, seamanship, and urban adventure. From the quiet harbors of Long Island Sound to the skyscrapers of Manhattan, this trip blends outdoor exploration, hands-on learning, and world-class cultural experiences.

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🌅 Day 1 – Arrive Port Washington → Long Island Sound

• Your group arrives in Port Washington to dinghy out to Boundless waiting at anchor.  Once aboard, you'll stow gear, receive a full vessel orientation, and talk through the exciting week ahead!

• In the afternoon we will sail across Long Island Sound, practicing steering, sail trim, lookout duty, and basic navigation.

• We will anchor for the night just before Throgs Neck Suspension Bridge in a cove.

• Evening is time for journaling, dinner aboard, and star-gazing at anchor.

🗽 Day 2 – Through Manhattan → Hudson River → Statue of Liberty Anchorage 

• After breakfast, we'll raise anchor and enter the East River, passing:

  • Throgs Neck & Whitestone Bridges

  • The famous Hell Gate tidal rapids (hold the wheel tightly!)

  • Ryker's prison

  • The United Nations Building

  • Manhattan’s East Side skyline

• We will continue down the East River, under the Brooklyn & Manhattan Bridges to

sail out into the Hudson River with views of:

• World Trade Center

• Empire State Building

• Ellis Island

• After sailing in front of the Statue of Liberty, we will drop anchor behind the Statue of Liberty for a once-in-a-lifetime overnight.

• Students cook dinner onboard, share stories, and enjoy sunset views of NYC.

🚇 Day 3 – Return to Port Washington

We will return to our departure point and travel the infamous East River to experience the Manhattan Skyline from the water.

• Breakfast, then up anchor dodging the NYC fast ferries as we make our way to the mouth of the East River.

• After our second transit of Hell Gate, we will return to Port Washington and tour the town! If the crew decides, dinner will be at the iconic Port Washington Diner.

• After dinner we'll walk down to the dinghy dock and go out to Boundless for an evening of movies, board games, cards, or music! 

🎭 Day 4/5 – NYC Exploration Day 2 + Broadway Show

A full city day taking the subway into downtown NYC to spend the day touring and shopping!

Activities may include:

• Times Square

• Rockefeller Center

• Central Park exploration & journaling

• Grand Central Terminal

• NYC Pizza lunch

• 9/11 Memorial & Museum

• Wall Street & the Charging Bull

• High Line Walk

• Chinatown & Little Italy for snacks and souvenirs

• Broadway Show in the evening (student-friendly production)

• Late-night subway trip back to the boat.

⚓ Day 6 – Full day of just sailing!

• Morning departure after breakfast, raise sails, and let the wind dictate where we go!

• Students practice:

  • Chartwork & plotting

  • Reading tides & currents

  • Knots and seamanship

  • Marine science observations in the Sound

• Return to Port Washington in time for dinner and our last night aboard.

​🌅 Day 7- Departure day...

• Breakfast aboard followed by a debrief of the week we experienced.

• After farewells and the signing of the guest book on Boundless, the group will take the subway to airports and/or train stations for the trip home...

Cost: $1,475 per student (based on 6) and includes 7 days/6 nights lodging on Boundless, a Captain and First Mate, all educational materials, instruction, museum entrance fees, dockage, fuel, and all meals on board. Meals ashore (group's choice), extra museums/events not on our itinerary, and/or airport pickup, additional. Airfare/transportation to/from NYC/Port Washington not included. A teacher attends for free including airfare with six students.

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This trip takes place in early summer and again in September. It is available in varying lengths and can be for adults, friends, scouts, and school groups!