Schooner Woodwind: Annapolis Sailing Cruises

Schooner Woodwind: Annapolis Sailing Cruises Sail aboard two identical, wooden 74-ft schooners from Annapolis, MD. www.schoonerwoodwind.com We sail seasonally from mid-April through October.
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Welcome Aboard... our two beautiful, wooden 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland. Annapolis is "America's Sailing Capital" in the heart of the Chesapeake Bay. Help raise the sails, steer the boat, or simply sit back and relax as "Woodwind" sails from the historic waterfront, past the Naval Academy and cruises into the Bay. Our staff is available year round to answer questions and help you plan your Woodwind sailing cruise!

Annapolis ➡️ Norfolk The first-ever 59º North Great Chesapeake Bay Schooner Race onboard the 74-ft. schooner WOODWIND is...
08/29/2026

Annapolis ➡️ Norfolk

The first-ever 59º North Great Chesapeake Bay Schooner Race onboard the 74-ft. schooner WOODWIND is coming October 12- 18.

Did you know 🤔
Andy sailed in the Schooner Race twice when working as a deckhand on WOODWIND in 2006 & 2007, and to this day it’s one of his favorites!

Yeah, this passage is a long-time coming, and has a lot to do with the origins of 59º North!

We still have 2 bunks available!

Link for more info: https://59-north.com/passage/2026-1-woodwind-great-chesapeake-bay-schooner-race?passage=recNMpgN3A7JkKFmD

Yep, come sail with us 😎1. Come Sail with Us by Elizabeth Jones, Bethesda, MD 2. Majesty by Drew Harding, Gettysburg, PA...
08/27/2026

Yep, come sail with us 😎

1. Come Sail with Us by Elizabeth Jones, Bethesda, MD
2. Majesty by Drew Harding, Gettysburg, PA-
3. The Bridge by Lauren Lennon, Bedford, NHjpeg
4. Living the Good Life by Pam Boon, Media, PA
5. Holl-ah-wwaaaayyy by Hayley Dino, Alexandria, VA
6. Come Sail Away by Elizabeth Jones, Bethesda, MD
7. My Wife Searching for Land by Ben Stentz, Rehobeth, DE
8. Captain for Five Minutes by Noah Crawford, Vancouver, WA
9. Garrett at the Helm by Margaret Wolf, Dallas, TX

📸 2026 Photo Contest

Glimpses of a beautiful History Monday evening spent with friends old and new 😎Thank you Dave Gendell !📸 Captain Jen (as...
08/25/2026

Glimpses of a beautiful History Monday evening spent with friends old and new 😎

Thank you Dave Gendell !

📸 Captain Jen (as a passenger 😉)

The best days are spent under sail ⛵️1. Sail Away Woodwind by Chasity Laumann, North Reading, PA2. Sail by Anna Sundwal...
08/23/2026

The best days are spent under sail ⛵️

1. Sail Away Woodwind by Chasity Laumann, North Reading, PA
2. Sail by Anna Sundwall, Valatie, NY
3. A View of our Twin by Janene Naugle, Reading, PA
4. The Crew by Alina Baymetova, Ashburn, VA
5. Woodwind Sail by Chasity Laumann, North Reading, MA
6. Back on the Chesapeake by James Sheppard, League City, TX
7. Captain Clover by Caroline and Clover Koca, Doylestown, PA
8. Captain Enrique by Antoinette Riehl, Huntongton, NY
9. Captain Sarah by Sarah Wolf, Atlanta, GA
10. Champagne on the Sea by Ryan Bruderer, Gilbertsville, PA

📸 2026 Photo Contest

The people we meet 😎 lucky us!1. Couple O' Captains by Bill Tingle, Alexandria, VA 2. Anniversary Night by Brandy Stubbl...
08/20/2026

The people we meet 😎 lucky us!

1. Couple O' Captains by Bill Tingle, Alexandria, VA
2. Anniversary Night by Brandy Stubblebine, Edgewater, MD
3. Carol Marie by David Scheib, Gettysburg, PA
4. Daughter's First Sailing Experience by Karen Chambers, Torrance, CA
5. DC Besties by Melissa Herendeen, Washington DC
6. Hello from Buckeye State by Tiffany Ford, Delaware, OH
7. Hutch Bros by Julie Hutchinson, Wake Forest, NC
8. Ladies First Sailing Experience by William Schnettler, Cincinati, OH
9. Love Us by Beth Srour-Williams, Arnold, MD
10. One Month by Emily Moses, Washington DC

📸 2026 Photo Contest

And then there were 2 😎 Only two more Wednesday Night Races!Woodwinds are ready to roll 🙌📸 Chasity Laumann, Reading PA20...
08/19/2026

And then there were 2 😎 Only two more Wednesday Night Races!

Woodwinds are ready to roll 🙌

📸 Chasity Laumann, Reading PA
2026 Photo Contest

Just another day aboard the Woodwind 😎1. The Chesapeake Bay Bridge by Lauren Lennon, Bedford, NH2. Annapolis at Sunset b...
08/16/2026

Just another day aboard the Woodwind 😎

1. The Chesapeake Bay Bridge by Lauren Lennon, Bedford, NH
2. Annapolis at Sunset by Twyla Walters, Norman, OK
3. Father's Day by Alexandra Brooks, Columbia, MD
4. Love of Sailing by Simone Lopez, Cedar City, UT
5. Newly Engaged by Rowan Treece, Annapolis, MD
6. Stormy Sail by Gina Shanfeld, St. Louis, MO
7. Sunset in June by Allison Alford, Gaithersburg, MD
8. Woodwind Cruise by Amarilis Blackwood, Forest Hills, NY
9. Father and Daughter Fun by Lily Lerman, Aldie, VA
10.Under the Bridge by Kym Hall, Annapolis, MD

📸 2026 Photo Contest

POV: Happiness 😎One of the most rewarding parts of our summer is the privilege to get these kids from the Seafarers out ...
08/14/2026

POV: Happiness 😎

One of the most rewarding parts of our summer is the privilege to get these kids from the Seafarers out on the water. For some, it’s their first time and for most they would never have the opportunity without the incredible benefits from the Virtual Schooner Race Education Fund!

* Please donate if you can-no amount is too small 🙏 https://gcbsr.app.neoncrm.com/Woodwind26VR

Address

80 Compromise Street
Annapolis, MD
21401

Telephone

+14102637837

Website

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