Annapolis Sailing Cruises: Schooner Woodwind

Two, 74ft schooners offer a real Chesapeake Bay sailing experience for public sails and private events. Buy a ticket or privately charter the entire boat. Learn about sailing, the ecology of the Bay as you sit back and relax with a cold beverage. A recognized Chesapeake Bay Storyteller, trained by the Maryland Office of Tourism.
Hours See website for hours.
80 Compromise St
Annapolis, MD
Get Directions
Local Phone:
  • Admission/Tickets Required
  • Catering Available
  • Educational Resources Available
  • Family-Friendly
  • Green Property
  • Group Tour Rates Offered
  • Group-Friendly
  • Guided Tours/Guide Available
  • Maximum Group Participants
  • Meeting Facilities
  • Student Group-Friendly
  • Video Link
Rated 5 by Jennifer G

May 24, 2023

Jennifer G

Our fourth felt like the first!!

This is our fourth sail on Woodwind and every time it feels like the first time! Whether we have Captain Mickey or Jen, they are always interesting and great hosts. Ed and Nellie were awesome, too...

Read More
Rated 5 by Holly L

May 15, 2023

Holly L

Great crew, great boat, great trip!

Capt. Mickey, Nellie, and Sam were all fantastic - professional, friendly, knowledgeable. They even let the kids on board help with the sails and steering. It was a beautiful and relaxing trip...

Read More
Rated 5 by Michele P

May 12, 2023

Michele P

Great birthday cruise

Perfect day on a great boat. This is the 3rd year that my friend and I have gone sailing for our mutual birthday celebration. Great crew, great boat and great weather! A guy from FL sailing with...

Read More

TripAdvisor Traveller Rating

Rated  based on 356 reviews
based on 356 Reviews
Read all the reviewsWrite a review