Girl Scout Cruises- How to get to 18 people

We are sorry to hear that these dates do not work for your group.  We can sail at your convenience, if you can get your group size to at least 18 people.

Ideas to Increase the Size of your Group

  • Invite another troop to join your troop.
  • Make your cruise a Mother-Daughter or Father-Daughter Event.
  • Invite the entire family, including siblings to join the troop. Everyone will enjoy the sail together!

A true and interactive sailing experience in Annapolis, Maryland on two, fast and fun 74-foot wooden schooners, Woodwind and Woodwind II for your Girl Scouts.

All Scouts will learn the following:

  • Nautical Terms
  • Hoist the Sails
  • Proper Lookout
  • Steer the Schooner
  • Boating Safety

We have developed a 2-hour sailing cruise where we train the girls on different aspects of sailing, as we cruise past the United States Naval Academy and then out onto the Chesapeake Bay.

Girl Scout Programs:


BROWNIES will take a “journey” learning about the “Wonders of Water” while sailing the Chesapeake Bay.  More Info on “Wonders of Water”

Girl Scouts Sailing in Annapolis on a SchoonerJUNIORS

Two programs to choose from, click here for the description of both programs.  Including a GEOCACHING TRAIL to obtain a “Geocacher Badge”.


TEENS will learn about “Smooth Sailing- your relationship with water”, and AMBASSADORS will be able to complete Step One of the “Water Legacy Naturalist Badge.”


Prices start at $32.00 per child (under 12) & come with a soft drink or bottled water, snack and a Schooner Woodwind Participation Patch!

According to the Girl Scout USA Safety Checkpoints, they want all girl scouts, adults, and other children aboard a “girl scout” cruise to be outfitted in life jackets. We have purchased Type III life jackets which are more comfortable for non-emergency use.

Call 410-263-1981 to arrange a cruise for your Scout Group.

© Copyright 2020. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. Annapolis MD. All right reserved. Privacy Policy.

Site Designed by: Green Mountain Marketing & Advertising, Inc.

Woodwind Annapolis Sailing cruises logo

Be the FIRST to know!


Sign up to get the latest info on Specialty Cruises, Events, and Opening. 

Thank you for signing up for Schooner Woodwind News. 

Schooner Woodwind