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!

🍾Brunch on the Bay- Wedding Crashers Style (20th anniversary)! Enjoy a movie themed brunch.  Join Captain Jen as she tel...
07/08/2025

🍾Brunch on the Bay- Wedding Crashers Style (20th anniversary)! Enjoy a movie themed brunch. Join Captain Jen as she tells tales about the filming of the movie and share your favorite memories of this cult classic. Food includes a crab cake (of course), meatloaf (Ma’s recipe), scallop wrapped in bacon and other fun themed items.

👀 “Sacked” Brunch Menu-a phenomenal sampling of finger food

Petite Crabcake-Thats What We Do with remoulade sauce
MA! The Meatloaf! Cold Meatloaf slider (Mom’s recipe)
Scallop wrapped in Bacon drizzled with Maple Syrup
House-made Old Bay Kettle Chips
Kitty Kat Chocolate Ganache Miniature Tart

(Book now- catering order is due by Thursday morning!)

Tickets: https://schoonerwoodwind.com/event/wedding-crashers-sacked-brunch-sail-2025/

July’s forecast: 100% good vibes 😎1. Relaxing before USNA I-Day! by Trish Heri, Parker, CO2. Sister Ship by Eliot Cranda...
07/08/2025

July’s forecast: 100% good vibes 😎

1. Relaxing before USNA I-Day! by Trish Heri, Parker, CO
2. Sister Ship by Eliot Crandall, Webster, FL
3. Sailors by Odutola, Windsor, MD
4. Shelby’s Summer Sailabration by Shelby Kenyon, Washington DC
5. Woodwind II from the deck of Woodwind I by Melissa Bilyeu, Clayton, NC
6. True Sailor by Stacy Brookes, Vienna, VA
7. Wedding Crashers Fun by Christine Vaughn, York, PA
8. Seas the Day with The Bay by Stefanie McAnally, Wayzata, MN
9. Six Months Before Christmas by Lynda Cooperrider, OH

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

What a great article that Megan from Yahoo about our upcoming events celebrating the Wedding Crashers 20th anniversary. ...
07/07/2025

What a great article that Megan from Yahoo about our upcoming events celebrating the Wedding Crashers 20th anniversary. Join the fun! http://bit.ly/4eFn6qE

Tickets for upcoming events: https://schoonerwoodwind.com/special-events/

Celebrate the 20th anniversary of Wedding Crashers in Annapolis with special sailing events aboard the real-life schooner from the film, including brunch cruises, trivia, and sunset Q&As with Captain Jen.

It's History Monday with James Ronayne aka Pork Chop 😎 History of Watermen on the ChesapeakeJuly 7th 6:30 pm - 8:30 pmAn...
07/07/2025

It's History Monday with James Ronayne aka Pork Chop 😎
History of Watermen on the Chesapeake
July 7th 6:30 pm - 8:30 pm

Annapolis is known as a seafood hub on the East Coast! But how many people truly know where their seafood comes from and how it is caught? For generations, Annapolis has been at the heart of the Chesapeake Bay’s seafood industry, sustained by the hardworking watermen who have navigated its waters.

Ride along to explore the rich history of seafood and the watermen of Annapolis, their traditions, challenges, and the evolving relationship between sustainability and the seafood industry.

🎟️ https://schoonerwoodwind.starboardsuite.com/

James Ronayne (aka Pork Chop) is a rising sophomore at Cornell University majoring in Environmental and Sustainability with a minor in Marine Science. An environmental photographer, conservationist, and storyteller, his work focuses on the Chesapeake Bay, highlighting its working watermen and environmental challenges. A columnist and staff photographer for Chesapeake Bay Magazine, he is actively involved in the Chesapeake Oyster Alliance and has testified before the Maryland Senate and Atlantic Fisheries Commission on environmental issues. Through his boat, PorkChop, and his camera lens, Ronayne captures the stories of the Bay, its waters, and its people.

📸 David Sites

Time drifts gently on the Chesapeake as the scenery rolls 1. Thomas Point Lighthouse by Tim Heibel, Annapolis, MD2. Vani...
07/05/2025

Time drifts gently on the Chesapeake as the scenery rolls

1. Thomas Point Lighthouse by Tim Heibel, Annapolis, MD
2. Vanishing Point by Chelsea Dorman, Silver Spring, MD
3. Quiet Night in Annapolis by Shanice Homeward, Pittstown, NJ
4. Osprey on the Water by Tammy Cross, New Kent, VA
5. Cargo Ship on the Chesapeake by Russell Wallace, Annapolis, MD

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

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/

Address

80 Compromise Street
Annapolis, MD
21401

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