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!

Vitamin Sea 😎1. Sunset Sail by Samantha MacKenzie, Severna Park, MD2. Sailing by the Rain by Elizabeth Jackson, Wellsbor...
09/09/2026

Vitamin Sea 😎

1. Sunset Sail by Samantha MacKenzie, Severna Park, MD
2. Sailing by the Rain by Elizabeth Jackson, Wellsboro, PA
3. Sunset from the Stern by Stephen Broderick, Severna Park, MD
4. Chilling at Sea by Michelle Espindola, Herndon, VA
5. Fun Adventure Day by Lauren Cialone, Washington DC
6. Harp by Donny Duong, Fairfax, VA
7. Port Tack by Scott Englund, N. Bethesda, MD
8.Woodwind Summer Cruise by Kaila Domanski, Colts Neck, NJ
9. Yes! by Catherine Davies, St. Augustine, FL

📸 2026 Photo Contest

Sailing into September⛵️1. September Sunset by Shira Goodman, Baltimore, MD2. Newly Empty Nesters Out to Forget Our Coll...
09/06/2026

Sailing into September⛵️

1. September Sunset by Shira Goodman, Baltimore, MD
2. Newly Empty Nesters Out to Forget Our College Kids by Shobha Whitacre, Severna Park, MD
3. Mini Captain by Emily Reash, Reston, VA
4. The Real Housewives of the Chesapeake by Reese LeQuire, Denton, TX
5. Furling the Sails by Melody Krapf, Taneytown, MD
6. Beautiful Night by Shobha Whitacre,
7. Captain my Captain by Risa Huber, Reistertown, MD
8. Looking up by Dawn Yost, New Market, MD
9. Hoist the Colors by Nathan Cryer, Reston VA
10. Family by Shelby Harding, Salisbury, MD

📸 2026 Photo Contest

More sailing please 😎1. Golden Hour Cruise by Dylan Crandall, Raynham, MA2. Sun, Sailing, and Fruit Snacks by Columbus, ...
09/03/2026

More sailing please 😎

1. Golden Hour Cruise by Dylan Crandall, Raynham, MA
2. Sun, Sailing, and Fruit Snacks by Columbus, OH
3. Little Sailor by Katie Brandyberry, Lancaster, PA
4. Fun on the Woodwind by Amy Neff, Columbus, GA
5. Still Sailing by Katie Brandyberry, Lancaster, PA
6. Pointing the Way by Jessica Orr Flinchum, Brandywine, MD
7. Wedding Party and Bride by Marc Andros, Houston, TX
8. Family by Andrew Gallagher, Feasterville, PA
9. A Lovely Day by Nancy McCarthy, Chester, MD

📸 2026 Photo Contest

The best sailing days of the season are yet to come 😎September schedule (through the 27th):10:00 - 12:00 (Saturdays & Su...
09/02/2026

The best sailing days of the season are yet to come 😎

September schedule (through the 27th):

10:00 - 12:00 (Saturdays & Sundays only)
12:30 - 2:30
3:00 - 5:00
5:30 - 7:30

Beginning the 28th:

11:00 - 1:00
1:30 - 3:30
4:00 -6:00

We still have our specialty cruises:

⚓️ History Monday
🍻 B**r Tasting Tuesdays
🥂 Sunday Funday

And we’re booking private events but it’s filling up fast!!

Come on out and sail with us!!

📸 Dianne Sullivan

Our passengers, our friends 😎1. Terry's Back!! by Sonali Gupta, Olney, MDSailing by Shuai Zheng, College Park, MD 2. Sai...
08/31/2026

Our passengers, our friends 😎

1. Terry's Back!! by Sonali Gupta, Olney, MDSailing by Shuai Zheng, College Park, MD
2. Sailing by Shuai Zheng, College Park, MD
3. Sailing by Ann Grabenbauer, Omaha, NE
4. Sailors in Training by Kim Lober, Silver Spring, MD
5. Sisters Steer by David Tucker, Olney, MD
6. Slight Lean by Jon Vandergrift, Harrisburg, PA
7. The Skipper by Karen Chambers, Torrance, CA
8. Tower of Metal by Sean McDermott, College Park, MD
9. Us by Matthew Killmeyer, Sterling, VA
10. Windswept by Kerry Branick Rockville, MD

📸 2026 Photo Contest

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

Address

80 Compromise Street
Annapolis, MD
21401

Telephone

+14102637837

Website

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