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Social Sailing Cruises

Schooner Woodwind, Annapolis Maryland Customer Testimonials Customer Reviews

“The Woodwind II is an amazing setting for a wedding and was such a special venue for the three of us to become a family together. We chose to have our ceremony on the Woodwind II so it would be a treat for our guests to get to go sailing and experience the Chesapeake Bay.  Many of our guests have asked us to get married every year so they can go back out sailing and have cocktails on the Woodwind!  It truly was perfect!”

Jessica and Geoff H.
Severna Park, MD

“We as well as our guests had an AMAZING time!! Everything ran very smoothly thanks to the planning and the CREW who were absolutely wonderful people! We had them all sign our boards (we had two mats to sign, one from the captain and crew with a great print of the Schooner and one we brought of our own which was a map of Annapolis).  The food was very very tasty and is still getting good reviews.”

Mike and Kristen J.

Make your next outing a nautical one! Experience sailing the Chesapeake Bay on an authentic 74-foot schooner!

Private cruises aboard the Schooner Woodwind offer your group exclusive use of one or both schooners and can accommodate up to 40 guests aboard each vessel.

Whether you are interested in hosting a birthday or anniversary celebration, getting married in an intimate setting, or just want to enjoy the historic skyline with a cold beverage and delicious catered treats, the Schooner Woodwind’s professional sales staff can help you plan every detail to make your next event a success.

Schooner Woodwind is perfect for your Social Event:

Raise the sails, steer the boat or simply sit back and relax with a cold beverage. The Schooner Woodwind captain and crew will make sure your trip is a memorable one.

If you are not interested in having exclusive use of the Schooner Woodwind, groups of up to 16 guests can purchase tickets for a flat fee on an upcoming public cruise before they become available to the general public.  Please visit our Group Sailing Page for more information.

Before You Call…
The friendly and professional Woodwind Sales Staff will help you plan every aspect of your special event. In order to help us tailor your trip to suit your needs, please have in mind the following information:

  • How large is your group?
  • What type of charter are you interested in?
  • Do you have a budget in mind?
  • Do you have a date in mind?
  • How long would you like to sail?
  • What time of day best suits your group?
  • Interested in catering? Select from appetizers to full meals!
  • Indulge with our different bar options: beer, wine, “specialty cocktail”, or premium bar!
  • Does your group have any other plans while in Annapolis?

Our event planners are seasoned Woodwind crew members and have years of experience organizing events aboard our boats. We look forward to planning the event of a lifetime for you and your group!

Schooner Woodwind sailing in Annapolis

Contact a Schooner Woodwind Sales Agent

Learn more about group sailing and sailing aboard the Schooner Woodwind & Woodwind II

Call 410-263-1981, or fill out an inquiry form by clicking on the button below.

Schooner Woodwind