Schooner Woodwind: Annapolis Sailing Cruises

11/08/2026

Still feeling it 😎

1. Annapolis Fall by Mike Heath, Millersville, MD
2. Amazing Experience by Kristy Gardner, North Beach, MD
3. At the Helm by Nazia Sbbadi, Rockville, MD
4. Birthday by Kate Heath, Millersville, MD
5. Brad Taking the Wheel by Susan Tousley, Annapolis, MD
6. Mid Day on the Bay by Ryan Patterson, Newtown Square, PA
7. Ron &BKelly by KellyLynch, Roanoke, VA
8. Sailing a Boat by Gwen Bowen, Falls Church, VA

📸 2026 Photo Contest

11/02/2026

The Final Sail of the Season! ⛵🍂

And just like that, another incredible season on the Chesapeake Bay has come to a close! It's been spirited and we're grateful to everyone who came aboard with us!

To our guests, crew, and to our awesome Annapolis hometown - thank you for another fantastic season!!

Fair winds and following seas until 2027 ⚓️

1. Halloween on the Woodwind by John Shutter, Ocean View, DE
2. Decked Out by Sebasion Wasinger, Washington DC
3. Stacks by Chris Drake, Washington DC
4. Fly the Flag by Ryan Patterson, Newtown Square, PA
5. He Loves It! Sarah Anderson, Deltona, FL
6. My Salty Dog by Jane Zimmerman, Arlington VA
7. Captain Delaney by Catharine Raby, Sterling, VA
8. Thomas Point by Caitlin, Biggins, Annapolis, MD
9. Old Woman and the Sea by James MacAllster, Gunnison, CO

📸 2026 Photo Contest

10/31/2026

👻 The scariest thing about Halloween? It’s our LAST DAY OF SAILING for the season! 🎃⛵

No tricks here, just one final chance to enjoy the magic! Come on out!

10/29/2026

Picture-perfect moments aboard Woodwind 😎

1. Splash Zone by Sarah Uong, Gaithersburg, MD
2. In Pursuit by Sarah Uong, Gaithersburg, MD
3. Osprey Liftoff by Osprey liftoff, Annapolis, MD
4. Peaceful Sail by Danielle Cherence, Red Bank, NJ
5. Sunset off the Bow by Laney Gibson, Wayne, PA
6. Sunset!! by Laney Gibson, Wayne, PA
7. Wedding Crashers by Brian DeMarco, Washington DC
8. Wedding Crashers by Gabby Mahoney, West Chester, PA
9. Woodwind II from Woodwind I by Dawn Parsons, Round Hill, VA

📸 2026 Photo Contest

10/22/2026

The end is near 😎

We have just a few days left in our season and would love for you to join us for a beautiful October sail!

11:00, 1:30, and 4:00 each day!

Hope to see you!

📸 David Sites David Sites

10/18/2026

Congratulations Captain Delaney and crew 🎉!!

From GCBSR:

Alright folks, sorry for the delay! Here are the results of the 2026 Great Chesapeake Bay Schooner Race. Congratulations to all the vessels & crews who participated! This year’s race featured shortened courses, with the Class N & combined Class B/C fleets sailing to Cove Point, while the Class A & AA fleets sailed to Smith Point.

Class N Fleet
Course: Cove Point, approximately 35 nautical miles

1st Place: GRACE
Corrected time: 11:32:23
Home port: Northeast, MD
Captains: Dobbs & Susanne Fryberger

2nd Place: BENNU
Corrected time: 12:06:56
Home port: Eastport, MD
Captain: Marco Ovando

Combined Class B/C Fleet
Course: Cove Point, approximately 35 nautical miles

1st Place: BONNY ROVER
Corrected time: 13:07:37
Home port: Norfolk, VA
Captain: Robert Suhay

2nd Place: SEA HAWK
Corrected time: 16:27:24
Home port: Portsmouth, VA
Captain: Steve Nelson

3rd Place: NORTH WIND
Corrected time: 17:22:35
Home port: Gloucester City, NJ
Captain: Scott Hughes

Class A Fleet
Course: Smith Point, approximately 70 nautical miles

1st Place: WOODWIND
Corrected time: 16:11:45
Home port: Annapolis, MD
Captain: Delaney Vorwick

2nd Place: ADVENTURER
Corrected time: 21:45:03
Home port: Annapolis, MD
Captain: Duncan Hood

3rd Place: TOM BOMBADIL
Corrected time: 23:37:34
Home port: Pasadena, MD
Captain: John Flanigan

Class AA Fleet
Course: Smith Point, approximately 70 nautical miles

1st Place: VIRGINIA
Corrected time: 22:11:52
Home port: Norfolk, VA
Captain: Michael Fiorentino

2nd Place: PRIDE OF BALTIMORE II
Corrected time: 24:16:16
Home port: Baltimore, MD
Captain: Jan Miles

Special Awards

Junior Sailor Award: Leela E.
Leela sailed aboard PRIDE OF BALTIMORE II & is an apprentice at the Alexandria Seaport Foundation. She was nominated by PRIDE II Chief Mate Taylor Methvan.

GCBSR Perpetual Trophy: WOODWIND
Awarded for the best corrected time across Classes AA, A, B & C at Thimble Shoals. WOODWIND recorded a corrected time of 29:31:34. Home port: Annapolis, MD.
Captain: Delaney Vorwick.

Black Dog Trophy: Duncan Hood

Thank you to the race committee, participating vessels & crews, photographers, spectators, volunteers, & supporters who make the Great Chesapeake Bay Schooner Race possible. Congratulations to all competitors on another memorable race!

We are still working through a large volume of photos from the race & events sent in from the fleet & spectators. We will be posting additional content as we get through it all. Cheers!

Schooner Woodwind: Annapolis Sailing Cruises World Ocean School Pride of Baltimore II Schooner Adventurer Schooner North Wind - Gloucester City, NJ YB Tracking SV Bennu Tugantine Norfolk Rebel

WOODWIND courtesy of Tom Konisiewicz.

10/16/2026

Captain’s Log: (earlier today)

I’m taking rest right now off watch, listening to the smooth sounds of water rushing (slowly) under the boat. As we ghost along at 3-4kts, it feels like a lifetime ago that we were ripping down the Bay from Baltimore hitting 10kts on a broad reach. In reality, it was just this morning.

We decided to favor the committee boat at the start. Even though this meant we couldn’t set the kite, Aidan worked out that it was a 1.5 NM advantage. Totally worth it. We were a little off on our timing but luckily Pride of Baltimore II took the reaching mark on the wrong side and we managed a big lead while they did a 360 penalty turn. Some close boat action made for an exciting and rewarding few minutes for all aboard.

Set the spin and kept it up until we couldn’t point and were making too much ground west. Expecting Easterly shifting winds, to Southerly late tonight (our specialty).

Parade of sail yesterday was stunning, no wind but a beautiful cruise around Baltimore Harbor. Glad we got to see some familiar faces there with us.

Delicious quiche this morning for breakfast, baked ziti tonight for dinner, and I’ve heard rumors of tiramisu for dessert…..

Alls well aboard the mighty ship Woodwind.
Capt Delaney

10/15/2026

United States Sailboat Show happening now 😎

Grab your Combo ticket and come see Ryan and the crew!

https://schoonerwoodwind.starboardsuite.com/

10/13/2026

⛵️ A TALE OF TWO SCHOONERS ⛵️

While Schooner Woodwind is Baltimore to take on the Great Chesapeake Schooner Race, Woodwind II is staying in Annapolis for the United States Sailboat Show!

⚓️ WOODWIND - Completed final preparations in Annapolis before heading to Baltimore for the the Parade of Sail, and the big race start on Thursday, October 15. Live tracker link: https://pro.yb.tl/gcbsr2026/

Captain Delaney Vorwick is at the helm and Aidan Gray is Mate.

⚓️ WOODWIND II - Will be at the United States Sailboat Show, October 15–18 at Dock F2. She’ll be sailing several times a day with combo tickets available for 90 minute cruises + discounted boat show admission. Ticket link: https://schoonerwoodwind.com/public-sailing-cruises-annapolis-maryland/sailboat-show/

Two adventures. One love of sailing.

10/09/2026

It’s US Sailboat Show Season 👏 October 15th-18th

Last year we began a new chapter at Schooner Woodwind and this year we’re super excited to bring it forward in a really big way!

Grab your combo ticket and have some fun with us!! https://schoonerwoodwind.com/public-sailing-cruises-annapolis-maryland/sailboat-show/

Our Sailing Combo-Ticket Deal lets you pair a 90-minute schooner cruise with your one-day Sailboat Show admission and save up to 40% on your show ticket!

What’s not to love? 😎

***Advance purchase required with limited walk-up sailing availability at Dock F2.