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!

Wind In Our Sails 😎1. Tranquility by Sangeeta Trip, Morganville, NJ2. Sailing by Jeff Rueckel, Annapolis, MD3. Sails by ...
06/13/2026

Wind In Our Sails 😎

1. Tranquility by Sangeeta Trip, Morganville, NJ
2. Sailing by Jeff Rueckel, Annapolis, MD
3. Sails by Jessie Alexander, Reading, PA
4. Sails Up by Devon Wurth, Phoenix, AZ
5. Sunny Skies Ahead by Brandy Lewing, Churchville, MD
6. Wind and Sails by Julie Saslow Schroeder, Silver Spring, MD

📸 Our photo contest is full on! For more details and to submit yours:
https://schoonerwoodwind.com/schoonerwoodwind-photo-contest/

June Happenings 😎⚓️ History Mondays⚓️ Beer Tasting Tuesdays ⚓️ Wednesday Night Races⚓️Sunset Sails⚓️ Sunday Funday We sa...
06/08/2026

June Happenings 😎

⚓️ History Mondays
⚓️ Beer Tasting Tuesdays
⚓️ Wednesday Night Races
⚓️Sunset Sails
⚓️ Sunday Funday

We sail everyday:

11:00 - 1:00
1:30 - 3:30
4:00 - 6:00
6:30 - 8:30

***Insider Tip: Our weekday sails are a perfect reset to your week!

Tickets available on our website!

June Beer Tasting Tuesdays 🍻 featuring DC Brau Brewing Company Sample while you sail! There will be representative aboar...
06/02/2026

June Beer Tasting Tuesdays 🍻 featuring DC Brau Brewing Company

Sample while you sail! There will be representative aboard to talk all things beer and answer any questions.

✅Your ticket includes two beers and one hard seltzer from DC Brau (other drinks available for purchase).

Tickets:
https:schoonerwoodwind.starboardsuite.com/e/tuesday-beer-tasting-6529

or:
[email protected]

DC Brau’s signature beers include: The Public (Pale Ale), The Corruption (IPA), The Citizen ( Belgian-style ale).

Cheers 😎

📸 David Sites

Today, we are especially grateful for those who continue to bridge our freedom from generation to generation. Thank you...
05/25/2026

Today, we are especially grateful for those who continue to bridge our freedom from generation to generation. Thank you ❤️🤍💙

📸 David Sites

One of the best parts of taking people out on the water is witnessing how nature has a way of gently returning them to t...
05/22/2026

One of the best parts of taking people out on the water is witnessing how nature has a way of gently returning them to themselves ✌️

1. Sailor's Daughter by Melissa Ni Vienna, VA.
2. At the Helm by Jim Shaw, Spartanburg, SC.
3. Proud Mom Watching her Son by Jessica Farrell, Annapolis MD.
4. Never too Young to Sail by Darcy Karnei Chester MD.
5. New Captain on Deck by Sergio Pimenta, Belo Horizonte MG.
6. Captain of the Ship by Megan Lanphere, Sinclairville, NY.
7. Forezzi Davis Family by Zoe Forezzi, Albany, NY.
8. Enjoying the Storm by Brielle Ferguson, Westminister, MD.

Enter our photo contest: https://schoonerwoodwind.com/schoonerwoodwind-photo-contest/

Experience the Annapolis to Bermuda Ocean Race start from the best seat on the Bay 😎Join us aboard the 74-foot Schooner ...
05/20/2026

Experience the Annapolis to Bermuda Ocean Race start from the best seat on the Bay 😎

Join us aboard the 74-foot Schooner Woodwind on June 5th for a special RACE WATCH CRUISE as hundreds of sailors begin their 753-mile journey from Annapolis to Bermuda.

This exclusive cruise gives you an incredible front-row view!

Departs:
Annapolis Waterfront Hotel�June 5 | 12:30 PM – 3:00 PM
$151.27 per guest

Your ticket includes:�• Flavor Fiesta snack box�• Bottled water & soft drinks�• Scenic race viewing aboard Schooner Woodwind

Craft beer, wine & bubbly available for purchase onboard.

Fiesta Snack Box Menu:�Corn Salsa • Guacamole • White Bean Dip�served with Corn Tortilla Chips

Whether you’re a sailing enthusiast or simply looking for a unique Annapolis experience, this is it!

Limited tickets available so reserve your spot today! https://schoonerwoodwind.com/event/annapolis-to-bermuda-ocean-race-watch-cruise/

Address

80 Compromise Street
Annapolis, MD
21401

Telephone

+14102637837

Website

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