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 553missyd

June 16, 2024


Perfect Annapolis Outing!

I’ve done this cruise about a dozen times with visiting friends and it’s always do ch fun. A real treat for visitors and me, every time! Highly recommend!

Read More
Rated 5 by Maureen B

June 13, 2024

Maureen B

Beautiful time on the water!

Although we didn’t have much wind, it was a beautiful sail on the water! The crew was very attentive and as a bonus, Michael gave us a water tour and shared history of the beautiful town of Annapolis...

Read More
Rated 5 by Travelbymail

June 12, 2024


Worth every penny

We took our Scottish friends for a late afternoon sail on Woodwind 11 and had a delightful time. Delaney, Makenzie and Michael made everyone feel very welcome and comfortable on board. It was a...

Read More

TripAdvisor Traveller Rating

Rated  based on 395 reviews
based on 395 Reviews
Read all the reviewsWrite a review