2024 Sailing Season is coming! See you April 13, 2024!

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

Mother’s Day Brunch

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

Our Mother’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, bacon & swiss quiche squares, blackened salmon with cusabi sauce served with hearty bread, grilled flank steak, fresh fruit salad, orange ... Read more

$92.00

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

Father’s Day Brunch

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

Our Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, bacon & swiss quiche squares, blackened salmon with cusabi sauce served with hearty bread, grilled flank steak, fresh fruit salad, orange ... Read more

$92.00

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

Mother’s Day Brunch

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

Our Mother’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food $94 per person, $54 per child. Maximum 35 guests.             Mother's Day Brunch Menu: Bacon, Ham, Caramelized Onion and ... Read more

$94.00

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

Father’s Day Brunch

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

Our Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food. $94 per person, $54 per child. Maximum 35 guests.         Father's Day Brunch Menu: Bacon, Ham, Caramelized Onion and Swiss Cheese ... Read more

$94.00

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

Schooner Woodwind
410-263-7837