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!

07/04/2025

🇺🇸 Sailing into Freedom

This 4th of July weekend, we’re grateful for the simple freedoms like the wind in our sails, the sunshine on the water, and the joy of sharing the Chesapeake Bay with good people.

Wishing everyone calm seas and a peaceful holiday.
See you on the water 😎

📸 Captain Jen

MDinfocus

Teamwork makes the Dreamwork😎1. Captain and Matey by Mary Decarlo, Millersville, MD2. Co-Captains by Palesa Hanc, Herndo...
07/02/2025

Teamwork makes the Dreamwork😎

1. Captain and Matey by Mary Decarlo, Millersville, MD
2. Co-Captains by Palesa Hanc, Herndon, VA
3. Soulmates by Michelle Krynski , West Grove, PA
4. At the Helm by Patrick McKern, Poulsbo, WA
5. Friends by Alan Schwartz Bala, Cynwyd, PA
6. Cozy Cruising by Mary Decarlo, Millersville, MD
7. Sailing in Annapolis by Angela Coladonato, West Chester, PA

📸 2025 Photo Contest https://schoonerwoodwind.com/schoonerwoodwind-photo-contest/

Sail with Us! https://schoonerwoodwind.com/public-sailing-cruises-annapolis-maryland/

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July's Beer Tasting Tuesday with DC Brau Brewing Company 🍻Join us for a 2-hour sunset sail while sampling 2 beers and 1 ...
07/01/2025

July's Beer Tasting Tuesday with DC Brau Brewing Company 🍻

Join us for a 2-hour sunset sail while sampling 2 beers and 1 premium hard seltzer from DC Brau. There will be a representative aboard to share a casual talk and answer questions. When finished with the sampling, you may purchase your favorite beers for the rest of the sail.

🎟️ https://schoonerwoodwind.starboardsuite.com

DC Brau Brewing Company is located on Bladensburg Road in NE Washington DC. http://www.dcbrau.com

DC Brau’s signature brews include: The Public (Pale Ale), The Corruption (IPA), The Citizen (Belgian-style Ale), Brau Pils (German-style Pilsner), and Penn Quarter Porter (Robust Porter), with seasonal and special brews available throughout the year including the award-winning On the Wings of Armageddon (Double IPA).

📸 David Sites

Lately 😎1. Making Memories on the Water by Jeff Anderson, Gibsonia, PA2. Close Enough by Sharon Oliver, Saint Joseph, MN...
06/28/2025

Lately 😎

1. Making Memories on the Water by Jeff Anderson, Gibsonia, PA
2. Close Enough by Sharon Oliver, Saint Joseph, MN
3. Joy of a Lifetime by Joseph Winkler, Belair MD
4. Woodwind II by Philippe Berteaud, Arnold, MD
5. Great Cruise by Allan Zacher, Lake Junaluska, NC
6. Captain Shah by Matt McDaniel, Austin, TX
7. D+C by Daniel Lloyd, Bowie, MD
8. Mom by Lindsay Cubbage, Lo

Sail with us! https://schoonerwoodwind.com
Photo Contest: https://schoonerwoodwind.com/schoonerwoodwind-photo-contest/

Between the Sheets1. Between the Sheets by Stephen Hudacko, New Market, MD 2. A Woodwind Sunset by Elizabeth OConnell, N...
06/26/2025

Between the Sheets

1. Between the Sheets by Stephen Hudacko, New Market, MD
2. A Woodwind Sunset by Elizabeth OConnell, New Market, MD
3. Peace After the Storm by Sally Damewood, Portland, OR
4. 75 Celebration by Lucy McCann Bethesda MD
5. Sunset on the Severn by Anne Klein, Charlotte, NC
6. Towards the Sky by James Luo, North Potomac, MD
7. Looking Up by Amanda Carpenter, Baltimore, MD
8. He's Helping by Tori See, Washington, DC

Sail with us! https://schoonerwoodwind.com
📸Photo Contest: https://schoonerwoodwind.com/schoonerwoodwind-photo-contest/

“Smell the sea, and feel the sky. Let your soul and spirit fly.” -Van Morrison1. Sunset at the Sunset Sail by Monica Arm...
06/21/2025

“Smell the sea, and feel the sky. Let your soul and spirit fly.” -Van Morrison

1. Sunset at the Sunset Sail by Monica Armijo Denver CO
2. Quiet Night in Annapolis by Shanice Homeward, Pittstown NJ

📸 2025 Photo Contest https://schoonerwoodwind.com/current-photo-contest-entries/


Sailing with rainbows 🌈 It never gets oldPhoto/Video by Captain Jen
06/19/2025

Sailing with rainbows 🌈 It never gets old

Photo/Video by Captain Jen

Making Memories on the Bay1. Father's Day Cruise by Marivic Murray, Severn, MD2. Baby on Board by Emily Dans, Severna Pa...
06/18/2025

Making Memories on the Bay

1. Father's Day Cruise by Marivic Murray, Severn, MD
2. Baby on Board by Emily Dans, Severna Park, MD
3. Dad in All HIs Glory by Shelley Gordon, Herndon, VA
4. Breezy Day on the Bay by Katie Vedete, Silver Spring, MD
5. Father's Day by Jared Brooks, Lanham, MD
6. Sailing Date by Matt McDaniel, Austin, TX
7. Tiny Captain by Jamie Malone San Luis Obispo, CA
8. Which Way is Up? By Whitney no Vickrey, Great Falls, VA

📸 2025 Photo Contest https://schoonerwoodwind.com/schoonerwoodwind-photo-contest/

Address

80 Compromise Street
Annapolis, MD
21401

Telephone

(410) 263-7837

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