Offshore Cruising Experience - 500NM / 7 Days
WAITLIST
Boat: Loki
Crew: Darren & Amanda
Price: $10,500 per cabin
Details:
Join us for a classic East Coast coastal passage from the two most iconic sailing ports: Newport, Rhode Island to Annapolis, Maryland. Timed perfectly for early fall sailing, this 7-day trip blends scenic coastal cruising with purposeful passage-making, offering a rewarding mix of iconic ports, tidal waterways, and a taste of offshore sailing. It’s an ideal opportunity to build confidence navigating busy waterways, timing tides, and planning longer legs, all while enjoying the charm of historic harbors along the way.
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This passage is designed around daytime sailing with evenings at anchor, with the option for one to two overnight sails depending on weather and timing. You’ll take part in route planning, sail handling, and navigation as we move steadily south, learning how to manage real-world coastal challenges like currents, traffic, and changing conditions.
Between sails, we’ll explore waterfront towns, enjoy meals aboard, and settle into the easy rhythm of life on the water. This is practical, confidence-building, hands-on, engaging, and deeply satisfying cruising.
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Training is tailored to your experience and interests, with opportunities to focus on:
Coastal route planning & tidal strategy
Navigation in high-traffic areas
Sail trim & helm control in varied conditions
Night sailing fundamentals (during overnight leg)
Anchoring, docking & canal transits
Communication systems & passage routines
Whether you’re preparing for longer passages or simply want to become a more confident coastal cruiser, this trip offers real-world experience in diverse sailing environments.
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We choose our itinerary based on the weather, but expect daily sailing activities and excursions from one picturesque anchorage to another. Some highlights include:
Long Island Sound – Protected waters, tidal awareness, and classic New England sailing
New York City – An unforgettable transit past the Manhattan skyline, anchor by the Statue of Liberty, and sail under iconic bridges
C&D Canal – Timing currents and transiting one of the East Coast’s most important waterways
Northern Chesapeake Bay – Wide open sailing, peaceful anchorages, and historic waterfront towns
Annapolis – A celebratory finish in the sailing capital of the Chesapeake
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Expect cooler, comfortable temperatures (65–75°F / 18–24°C), steady breezes, and less summer traffic. Weather systems can be more dynamic, offering excellent learning opportunities to learn more about weather routing and departure planning while still providing beautiful sailing days and picturesque anchorages.
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Start: Newport, Rhode Island
Finish: Annapolis, Maryland
Fly into Providence (PVD) or Boston (BOS) for arrival
Fly out of Baltimore (BWI) or Washington, DC (DCA/IAD)
We recommend arriving the day before departure and arranging flexible travel where possible. Final boarding details will be provided prior to the trip.
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Our prices are all-inclusive once aboard, covering meals, snacks, refreshments, evening sundowners, and mooring or docking fees. Not included: Transportation to/from the program and meals/drinks ashore.
Private Double Cabin - $10,500*
*Price per cabin, which may accommodate one or two persons.
Book the whole boat (up to 4 guests) and receive a 10% discount.
Extra Night Aboard - $600
Click ‘Book Now’ and fill out a submission form. We will get back to you with an invoice to reserve your cabin. After booking, we will send you more information about the passage including details on what to expect on your stay aboard, boat details, packing, etc. If you have any questions, don’t hesitate to Contact Us! Or, maybe your questions are answered elsewhere? Check out our FAQ’s!