12 Days | Hudson River • New York City • Jersey Coast • Delaware River • Chesapeake Bay
🌉 Day 1: Hudson → Croton-on-Hudson (55 NM)
Sail down the scenic Hudson River, surrounded by rolling hills, fall foliage, and history. Pass under the Rip Van Winkle, Kingston-Rhinecliff, and Mid-Hudson bridges. You’ll navigate past West Point, scenic cliffs, and the Hudson Highlands—ideal terrain for helming and navigation.
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🗽 Day 2: Croton-on-Hudson → Liberty Landing Marina, NYC (45 NM)
Continue south into the dramatic Hudson Palisades. Pass under the George Washington Bridge before the skyline of Manhattan opens ahead. Sail by Ellis Island, Manhattan, and Lady Liberty herself. Dock at Liberty Landing Marina—a luxury base with city views.
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🏙 Day 3-4: Liberty Landing – Lay Day in New York City
Take a full day to enjoy New York City. Crew may visit Central Park, museums, Broadway, or just relax dockside. Vessel preparation and provisioning for the offshore legs occur here.
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🌊 Day 5-6: NYC → Atlantic City (115 NM)
Depart NYC for an overnight coastal passage along the Jersey Shore. This offshore leg is the first open water night sail of the trip. Crew will rotate through night watches, monitor AIS, and sail under the stars.
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🌊 Day 7-8: Atlantic City → Delaware City (100 NM)
Another overnight passage, this time heading south along the coast before turning up the Delaware Bay. The trip requires attention to current timing and approach planning for the shallow channels.
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⚙️ Day 9: Delaware City → Annapolis (60 NM)
Transit the C&D Canal, a manmade waterway linking the Delaware River to the Chesapeake. Once through, enter the upper Chesapeake Bay and sail south to the historic sailing capital of Annapolis.
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🌅 Day 10: Annapolis → Solomons Island (45 NM)
Cruise down the middle Chesapeake Bay, flanked by the eastern and western shores of Maryland. The sail is relaxed and scenic, with open stretches perfect for sail trim practice and watch training.
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🌊 Day 11: Solomons → Hampton Roads (65 NM)
Final leg! Sail through the southern Chesapeake past naval installations, tall ships, and container ports as you approach Hampton Roads. This stretch features a mix of open sailing and high-traffic harbor approach.
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🧳 Day 12: Departure from Hampton Roads
Disembark, transfer to airport or hotel, and celebrate a voyage well earned—over 500 nautical miles of varied sailing through the historic eastern seaboard.
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🧠 Crew Skills Gained (Hudson to Hampton Roads)
This leg of the journey transitions from inland river navigation to offshore and coastal cruising, offering crew members the opportunity to deepen their sailing competence in diverse environments.
This passage is ideal for sailors looking to move beyond inland or lake sailing into real-world cruising scenarios, offering confidence-building experience across multiple marine environments.
When considering chartering a yacht in Canada, we know you have many options. Some of these options look super exciting and at ridiculously great prices. Recent trends in the industry have opened the door for many unqualified individuals to purchase boats and offer charter services to the unsuspecting public. It’s easy to create a website and even easier to just list a boat on sites such as Facebook Marketplace, Kijiji, Getmyboat, Boat Setter and many others.
Unfortunately, many of these operators are NOT licensed, insured or qualified to accept your trust on the water.
In order to be licensed and insured a number of items MUST be in place. Listed are just a few.
Over the last few years there have been a number of deaths and even more accidents resulting from these types of operators. Be safe and know who you are getting on a boat with. All licensed operators should willingly display their credentials, and most are members of the Passenger & Commercial Vessel Association (PCVA).
