Annapolis Sailing Cruises: Schooner Woodwind

Visit Website

Get Directions

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.

Location

80 Compromise St

Annapolis MD 21401

Get Directions

Contact

Map

Central Maryland

	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 80 Meeting Facilities Student Group-Friendly Tour Length 2 hours or more Video Link https://www.youtube.com/watch?v=WTQCReY96r8&t=10s Weddings

May 25, 2026

Jennifer R

Graduation trip with family and friends

The staff and overall experience was amazing!! I highly recommend.

May 21, 2026

Mark F

Great experience

This would be a totally excellent experience except for the drinks... The crew is friendly and funny. They give you lots of interesting information and fun stories. You get to help raise the sails...

May 06, 2026

scottbM7167EK

Great experience with 20 knot winds

Awesome experience, we had good winds. We sailed on a Tuesday in May so there was only one other couple with us. They limit the max passenger capacity to 30 so we had all the captain's and crews...

TripAdvisor Traveller Rating

based on 450 Reviews

Read all the reviews Write a review