Schooner Woodwind

Now Sailing for the 2026 Season — Book Your Cruise Today!

She said OF COURSE!

Man proposing to women on schooner deck with a ring box open

The Schooner Woodwind was one of the first dates my girlfriend (now fiancee!) and I went on in 2015 and we had the most amazing time. When I started planning the proposal, I knew I wanted to make it special and the Schooner Woodwind instantly came to my mind. The forecast had called for rain … Read more

Woodwind Sunset

Schooner sailing into big yellow sunset over Annapolis

Taken on 5/18/2017 on a corporate cruise. What a great way to end a long day of strategy sessions. Photo by Joseph Baweja of Suwanee, GA

The Bay Bridge

Black and white photo from stern of schooner with Bay Bridge

The wind was so strong, we reached the bridge in little to no time at all! Photo by Gregg Anderson of York, Pennsylvania

Friend and Family Kweens Aboard

Group enjoying a birthday party on the schooner with Oriental Umbrellas

Look at my life; look at my choices. On this day of my 35th birthday I chose to indulge each of us with sun, history, laughter and the breezes off the waters of Annapolis, Maryland. Still young, but 35 gave me pause. I live in choices, including those I surround myself with. The people in … Read more

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