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Sailing Made Even More Interesting


Sailors NYC together with the Annapolis Sailing School are offering an opportunity to sail on 5- day trips between the two cities. Chesapeake Bay, Cape May, Atlantic City, The Jersey Shore and NYC - are the highlights of where you will get to sail. 

Who Is Coming


The 5-day long trips will accommodate 2-4 passengers onboard a Beneteau Oceanis 37' and will be accompanied by a highly experienced USCG Master and ASA instructor. The cruises are primarily offered for certification purposes, but someone who wants to join as a charter passenger is also welcome.

American Sailing Association Certication


Get your continuing and advanced certifications with us! ASA 103 (Basic Coastal Cruising) and ASA 104 (Bareboat Cruising) are offered together on three cruises (see dates below). ASA 106 (Advanced Coastal Cruising) is offered in a fourth cruise (see date below). Check out pre-requisitis for each course on ASA.com



  • Tuesday evening - Arrive at Annapolis Sailing School, over night on board

  • Wednesday - Depart Annapolis Sailing School 9am - sail northeast on the Chesapeake Bay towards Chesapeake & Delaware Canal, overnight in Bohemia river (just south of the canal entrance) or stay mid canal at the Georgetown Basin

  • Thursday - Traveling through the Chesapeake & Delaware canal and into the Delaware Bay and then south easterly down the Delaware Bay to an evening docking at Cape May, New Jersey

  • Friday - Sail northward along the Jersey Shore to Atlantic City

  • Saturday: Overnight passage to the approaches to New York City


Itinerary NYC >> Annapolis - same in reverse



  • Annapolis >> NYC - September 27-October 2 - Course - ASA 103-104

  • NYC >> Annapolis - October 4-8 (arrive in time for 2016 Annapolis Boat Show - October 6-10) - Course - ASA 103-104 OR ASA 106


ASA 103-104 courses: $2,750

ASA 106: $2,950

Charter Passenger: $2,650

Prices include: 

  • 5 days (4 nights) accommodation on board

  • Full provisioning (except specialty foods, most special requests, and alcohol)

  • All safety equipment required by the USCG and navigation aids 

  • Pre- and post-cruise Fuel and water

  • Pre- and post cruise boat cleaning

  • Galley Equipment

  • Dock and port fees as well as boat taxes

  • ASA books and certification fees (when applicable)


  • Transportation to/from Annapolis or New York City is not included. Note: Transport from transportation hubs near Annapolis (BWI Airport, BWI Airport Amtrak Station, or New Carrollton Amtrak Station) can be arranged in advance. 

  • Land accommodations

  • Personal Travel Insurance

  • Meals in restaurants

  • Provisioning – specialty foods, most special requests, and alcohol