Schooner Woodwind

Skip to content

2025 Sailing Season Has Ended, we will start sailing again mid-April 2026!

Home
Public Cruises
Private Cruises
Special Events
Schooner Racing
Ship’s Store
- Ship’s Store Merchandise
- Schooner Woodwind Gift Certificates
410-263-7837
Buy Tickets

Sails Up

November 5, 2025 by Green Mountain 1

Enjoying a beautiful October afternoon

Photo by Chris Cuneo of Greenville, SC

Categories 2025 Photo Contest

Woodwind at Thomas Point Light

Promotions & Deals
Photo Contest
Sign up for Email!

About Us

About Us
About the Boats
Fun Facts
Photo Gallery
Videos
Educational

FAQs

FAQs
Parking and Directions
Printable Brochures
Photo Gallery

Ship’s Store

Tickets on Sale Now
Merchandise
Gift Cards
Promotions & Deals

Around Town

About Annapolis
Local Weather

Contact Us

Get in Touch
Send us an Email
Employment Opportunities

Facebook
Instagram
YouTube
X

Schooner Woodwind • at the Annapolis Waterfront Hotel • 80 Compromise Street • Annapolis, MD 21401 • 410-263-7837

© Copyright 2025. Running Free, LLC DBA Annapolis Sailing Cruises: Schooner Woodwind. Annapolis, MD. All rights reserved. Privacy Policy. Site Designed by: Green Mountain Marketing & Advertising, Inc.

Public Cruises
Private Cruises
Special Events
Team Building
Groups
- Student Groups
- Back
Ship’s Store
Rates and Schedule
Buy Tickets

410-263-7837