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!

Your pot of GOLD 😎🌟 Located in Annapolis, MD🌟 Must work at least 3 full days per week 🌟 Some positions run until Novembe...
02/22/2025

Your pot of GOLD 😎

🌟 Located in Annapolis, MD
🌟 Must work at least 3 full days per week
🌟 Some positions run until November

For more information or to apply:
https://schoonerwoodwind.com/employment/

Winner of our 2025 Valentines Day Drawing 🎉Congratulations Kimberlykay1 @ Kimberly Mcfarland-Cox 🥳 We look so forward to...
02/14/2025

Winner of our 2025 Valentines Day Drawing 🎉Congratulations Kimberlykay1 @ Kimberly Mcfarland-Cox 🥳 We look so forward to seeing you aboard the Woodwind this season!!

Photo credit: Dick Williams

Never forget your Woodwind koozie on vacation! Capt. Jen (and Rich) relaxing at a beach bar on a barrier island off of F...
02/10/2025

Never forget your Woodwind koozie on vacation! Capt. Jen (and Rich) relaxing at a beach bar on a barrier island off of Faro in Portugal 🇵🇹

Time off after a busy season is needed. Last year she was crossing the Atlantic, now she's admiring it from the beach.

In the name of Cupid 💘We’re giving away TWO FREE TICKETS 🎟️🎟️ to sail the Woodwind in the 2025 season and a bottle of B...
02/09/2025

In the name of Cupid 💘

We’re giving away TWO FREE TICKETS 🎟️🎟️ to sail the Woodwind in the 2025 season and a bottle of BUBBLY 🥂

To Win- Like, tag, comment, share, and follow

🌹LIKE this post
🌹TAG someone in the COMMENTS that you’d like to join you on this sail!
🌹SHARE this post in your STORY
🌹FOLLOW us if you don’t already

This will qualify you for the random drawing that will take place on February 14th!!

Ready,set, go!

You have until 11:59 on February 13th 😎 The winner will be contacted through social media.



***some sailing dates may be restricted for ticket redemption

POV: When your future self whispered JOIN THE WOODWIND TEAM and you’re ecstatic you did 😎What did you learn on the Woodw...
02/04/2025

POV: When your future self whispered JOIN THE WOODWIND TEAM and you’re ecstatic you did 😎

What did you learn on the Woodwinds that makes you more successful now?

“I quite literally learned first-hand how to run a small business by combining passion, hard-work, and genuine care for the staff and customers. Sailing-wise, I learned how to really ‘sail’ a boat, to get the most out of her in all conditions and especially to sail comfortably in close-quarters (we named our little side cannon business Harborburn for a reason!).”
- Andy Schell, 59 North Sailing

WE’RE HIRING:
https://schoonerwoodwind.com/employment/

🌟 Great “sea time” for a Captain’s License
🌟 Must work at least 3 full days
🌟 Positions start in March, April, or May and some run until November

What an honor! Look who's on the front cover of Visit Annapolis Visitors Guide for 2025! Thank you Jay Fleming, Photogra...
01/29/2025

What an honor! Look who's on the front cover of Visit Annapolis Visitors Guide for 2025! Thank you Jay Fleming, Photographer for the fantastic photo.

"I'm saddened to share that Captain Mike Oh passed away last Thursday after a six-month battle with cancer. Mike was a c...
01/27/2025

"I'm saddened to share that Captain Mike Oh passed away last Thursday after a six-month battle with cancer. Mike was a captain and maintenance guru for the Schooner Woodwind for roughly 5 years, 2010-2015. He was funny and silly, and calm under pressure. He enjoyed sharing his enthusiasm for the Chesapeake with everyone he sailed with.

I've included some favorite photos of Mike from over the years on the Woodwind and from the Great Chesapeake Bay Schooner Race. He made the boating world a better place with his genuine spirit, willingness to help others and the well placed googly eyes that we still find years later. Mike will be deeply missed." - Captain Jen

Reminder-- register before Sunday, January 26 at 11:59 pm! Blue Angels Cruise! 👀 May 21 from 11:30-3:30.There will be a ...
01/24/2025

Reminder-- register before Sunday, January 26 at 11:59 pm!
Blue Angels Cruise! 👀 May 21 from 11:30-3:30.
There will be a random draw to determine who will be able to buy tickets aboard the Woodwind to watch the Blue Angels Show. We have only 30 tickets available to sell. Last year we had 250 people register to buy tickets.
- Price per ticket is $192.05 which includes lunch, soda and water.
- All duplicate entries will be deleted.
- All entries will go through a random picker app. We will email (and text) you on Monday, January 27 if your name gets picked to buy tickets.
- You will have until Wednesday, January 29 by 1pm to call in and buy your tickets. You may purchase a maximum of four tickets.
- We will continue to use the random picker until all tickets have been purchased. Another random draw will happen later Wednesday, January 29, then on Friday, January 31 and Tuesday, February 4 if needed.
Fill out this form: https://forms.gle/DVxL8mwpXfgnDBa29

Register now for the Blue Angels Cruise! 👀There will be a random draw to determine who will be able to buy tickets aboar...
01/23/2025

Register now for the Blue Angels Cruise! 👀

There will be a random draw to determine who will be able to buy tickets aboard the Woodwind to watch the Blue Angels Show on May 21 from 11:30-3:30. We have only 30 tickets available to sell. Last year we had 250 people register to buy tickets.
- Price per ticket is $192.05 which includes lunch, soda and water.
- You will have from now until Sunday (January 26) at 11:59 pm to register at the link below.
- All duplicate entries will be deleted.
- All entries will go through a random picker app. We will email (and text) you on Monday, January 27 if your name gets picked to buy tickets.
- You will have until Wednesday, January 29 by 1pm to call in and buy your tickets. You may purchase a maximum of four tickets.
- We will continue to use the random picker until all tickets have been purchased. Another random draw will happen later Wednesday, January 29, then on Friday, January 31 and Tuesday, February 4 if needed.

Fill out this form: https://forms.gle/DVxL8mwpXfgnDBa29

More projects on the Woodwinds during the winter season. Great team doing the work. Shout outs to Delaney, Joe, Jacob, ...
01/14/2025

More projects on the Woodwinds during the winter season. Great team doing the work. Shout outs to Delaney, Joe, Jacob, Mickey and Michael!

On this cold Saturday, we’re reflecting back on a fun-filled 2024 and looking forward to all that 2025 will bring! Stay ...
01/11/2025

On this cold Saturday, we’re reflecting back on a fun-filled 2024 and looking forward to all that 2025 will bring!

Stay warm and think sailing 😎

How fun is this!!! Drew, the coyote that protects the Thomas Point Lighthouse, has just come out with a book this week a...
12/24/2024

How fun is this!!! Drew, the coyote that protects the Thomas Point Lighthouse, has just come out with a book this week and Woodwind is in it! He had this adventure this summer.

All proceeds from the sale of this book will go directly to the Thomas Point Shoal Lighthouse for continuing preservation. Thanks David Sites for the images.

Here’s the link… 🔗

Drew's Grand Adventure https://a.co/d/dfdtpnc

Buy together with a Woodwind gift certificate for a fun combo.
https://schoonerwoodwind.com/ships-store/schooner-woodwind-gift-cards/

More maintenance fun on the boats. We had to replace the cutless bearing. This is where the propeller shaft goes through...
12/20/2024

More maintenance fun on the boats. We had to replace the cutless bearing. This is where the propeller shaft goes through the strut and then into the engine.

Holiday reminder, when you buy local it puts wind in our sails! ❤️ Woodwind gift certificates make great last minute gifts. Simple to buy, print or email to your friends or family! https://schoonerwoodwind.com/ships-store/schooner-woodwind-gift-cards/

And we have a Winner in our 2024 Photo Contest for the Schooner Woodwind! Congratulations to Ken Smith from La Plata, MD...
12/18/2024

And we have a Winner in our 2024 Photo Contest for the Schooner Woodwind! Congratulations to Ken Smith from La Plata, MD and his photo "A Bridge too Far" . Thank you to everyone who voted.

It is not too late to get your loved one the gift of sailing. Gift certificates can be printed at home or sent by an email. Quick and Easy! https://schoonerwoodwind.com/ships-store/schooner-woodwind-gift-cards/

📷 Last call! Vote for your favorite photo before 1pm today! Just a click will make someone's day! Thanks! ❤️
12/18/2024

📷 Last call! Vote for your favorite photo before 1pm today! Just a click will make someone's day! Thanks! ❤️

Please remember to vote on your favorite photo or photos. This contest runs till 1pm tomorrow.
12/17/2024

Please remember to vote on your favorite photo or photos. This contest runs till 1pm tomorrow.

Address

80 Compromise Street
Annapolis, MD
21401

Telephone

(410) 263-7837

Website

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Videos

On the Cover 😎 What an honor to be on the front cover of Visit Annapolis Visitors Guide for 2025! Thank you Visit Annapolis for the huge surprise and all that you do for Annapolis tourism!! And thank you to the amazing Photographer, Jay Fleming for the fantastic photo! Let’s make 2025 a best year ever 🙌 #sailthewoodwindawhile #visitannapolis #jayflemingphotography #chesapeakebay #maryland

The big reveal with Jay Fleming at the Visit Annapolis annual meeting for the Visitor Guide cover. We love it!

Schooner Woodwind Gifts for you 🎁 https://schooner-woodwind-ships-store.myshopify.com/ #sailthewoodwindawhile #holidays #sailing #schooners #visitmaryland #visitannapolis

Ornaments
Ornaments

You asked for it and now we have more Schooner Woodwind Ornaments!! Thank you Citizen Pride! https://schooner-woodwind-ships-store.myshopify.com/products/schooner-woodwind-ornaments #sailthewoodwindawhile #sailinggifts #visitannapolis #maryland #chesapeakebay #holiday

One minute working with the clear, plastic shrink wrap.

Woodwind II Rising 😎 #sailthewoodwindawhile #schooners #annapolis

2024 Woodwind II

How Cool 😎 So much fun sailing in a race on Woodwind II with @capt_glennshephard & Colin @sailingparlayrevival during the Annapolis Boat Show! Thank you to everyone who made this possible @sailingbc @svdelos @schmoopsadventures Let’s do it again! Stay cool 🤙 Videos by @sailingbc 📸 Captain Jen and Schmoops Adventures #sailthewoodwindawhile #annapolisboatshow #sailingparlayrevival #captainglenn #svelos #sailingbc #visitannapolis #visitmaryland #tripadvisortravellerschoice2024 #spinsheet #chesapeakebaymagazine #hellyhansen #quantumsails #utube #sailing

How to find the Schooner Woodwind at the US Sailboat Show. (hint at the very end of dock F2). We will be sailing a few times today. If you want to sail with us, buy your combo tickets at least one day in advance or buy your tickets at our booth. More info: https://schoonerwoodwind.com/public-sailing-cruises-annapolis-maryland/sailboat-show/

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