Schooner Woodwind

Thank you for a great sailing season. See you in April 2025!

Brunch Sail with Michael Tolcher

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

An Intimate, All Ages Acoustic Show with MICHAEL TOLCHER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Michael Tolcher will play acoustically while at anchor in a secluded cove. He will play for about an hour and after the performance we will set sail on the 74-foot, classic wooden ... Read more

$92.00

Brunch Cruise with Jay Nash and special guest, Natalia Zukerman

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

An Intimate, All Ages Acoustic Show with JAY NASH and special guest, NATALIA ZUKERMAN aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Jay Nash will play acoustically while at anchor in a secluded cove. He will play for about an hour and after the performance we will ... Read more

$99.00

Brunch Sail with Jesse Ruben

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

An Intimate, Acoustic Show with JESSE RUBEN aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch and a relaxing sail. Jesse Ruben is a Philly born singer/songwriter currently living in Brooklyn. His songs have been heard on TV shows such as One Tree Hill, Degrassi, Switched at ... Read more

Acoustic Brunch Sail with Ink + Ash (feat. Gareth Asher + Nicki Thrailkill)

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

An Intimate, Acoustic Show with Ink + Ash (feat. Gareth Asher + Nicki Thrailkill) aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch on Memorial Day. Band's BIO: In this life, we spend our days in blissful ignorance as to what lies ahead. We work, we play, we ... Read more

Fireworks Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Join us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30 pm for a sunset sail with live entertainment by "Ship's Company". We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the ... Read more

$91.00

Brunch Sail with Ernie Halter

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

An Intimate, All Ages Acoustic Show with ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Ernie Halter will play acoustically while at anchor in a secluded cove. He will play for over an hour and after the performance we will set sail on the 74-foot, ... Read more

$91.00

Brunch Sail with Tony Lucca

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Back for a 7th performance on the Schooner Woodwind! An Intimate, Acoustic Show with TONY LUCCA aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch and a relaxing sail. Tony Lucca is a Nashville-based singer/songwriter whose catalog of music runs the gamut from soul-infused pop to tear-jerker ... Read more

$111.00

Acoustic Brunch Sail with Gareth Asher

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

An Intimate, Acoustic Show with Memorial Day favorite, GARETH ASHER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Gareth Asher returns for an Acoustic Brunch Sail aboard the Schooner Woodwind promoting his new album, “Defend the Flame.” With lyricism reflecting and celebrating the inner struggles we face through ... Read more

Fireworks Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Join us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30 pm for a sunset sail with live entertainment by "Ship's Company". We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the ... Read more

$93.00

Brunch Sail with Jesse Ruben

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

An Intimate, Acoustic Show with JESSE RUBEN aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch and a relaxing sail. Jesse Ruben is a Philly born singer/songwriter currently living in Brooklyn. His songs have been heard on TV shows such as One Tree Hill, Degrassi, Switched at ... Read more

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