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, quiche lorraine squares, blackened salmon with cusabi sauce served with hearty bread, grilled flank steak, fresh fruit salad, orange juice and ... Read more

$90.00

Sunset Sail with Stefan Heuer Music

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

Stefan Heuer is a singer songwriter residing in Annapolis, Maryland. His original music as a solo performer has reached ears all over the world. Stefan performs at venues in Annapolis and around the DMV area. Stefan mirrors elements of folk, but his original music holds a strong foundation of blues and soul.   Band's Website ... Read more

May Lighthouse Cruise

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

Sail to as many as three different lighthouses on the Chesapeake Bay and learn about their history, importance, and present day condition by a guest lecturer from the Chesapeake Chapter of the U.S. Lighthouse Society. Depart Annapolis at 10:30am, return at 2:30pm, includes soft drinks and snacks, $79 per adult, $52 per child with child’s ... Read more

Cancelled due to Private Event: Sunset Sail with Matt & Katie (of The Stick Mob)

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

Matt and Katie play with the Stick Mob, a folk-ameri-something-grass-n-stuff quintet from the hillbilly wilds of the nation's capital. They love to play and sing beautiful old melancholy tunes as well foot-stomping originals.     Band's Website https://thestickmob.bandcamp.com/ Band's Facebook Page https://www.facebook.com/pages/The-Stick-Mob/165403906811064?fref=ts

$46.00

Acoustic Sunset Sail with Paul Pfau

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

An Intimate, All Ages Acoustic Show with PAUL PFAU aboard the Schooner Woodwind for a concert on a beautiful sailing boat. Nashville’s Paul Pfau (rhymes with "wow") is a modern-day troubadour, a skilled and eager listener, with a gift for setting the truths of love, life and loss to music.  His talent for taking in and re-interpreting ... Read more

Saturday Night Sailor’s Delight Cocktail Cruise

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

Sail away on one of our first sunset sails of the season. Enjoy great appetizers, cocktails, wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, two drink vouchers and a sunset sail.  Depart Annapolis at 5:30 pm, return at 7:30 pm.  Tickets are $74 per adult with a maximum of ... Read more

$74.00

Friday Night Sailor’s Delight Cocktail Cruise

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

Sail away on one of our first sunset sails of the season. Enjoy great appetizers, cocktails, wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, two drink vouchers and a sunset sail.  Depart Annapolis at 5:30 pm, return at 7:30 pm.  Tickets are $74 per adult with a maximum of ... Read more

$74.00

Acoustic Brunch with Jay Nash

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

Announcing a Schooner Woodwind exclusive event!  The influences of being on the water, enjoying great food and beverage can create great memories.  However, when you combine those two elements with live music you are now on a journey. We invite you to join us as Captain Jen navigates us out of Annapolis Harbor for a ... Read more

$135.00

Sunset Sail with “The Stick Mob”

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

Matt and Katie play with the Stick Mob, a folk-ameri-something-grass-n-stuff quintet from the hillbilly wilds of the nation's capital. They love to play and sing beautiful old melancholy tunes as well foot-stomping originals. The Stick Mob performing on the Woodwind 2014   Band's Website http://www.reverbnation.com/thestickmob Band's Facebook Page https://www.facebook.com/pages/The-Stick-Mob/165403906811064?fref=ts  

Classic Wooden Boat Regatta

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

Participate in the National Sailing Hall of Fame Classic Wooden Boat Regatta. They have invited the Woodwinds' to participate in the race in the "Spirit of Tradition Class". The course is approximately 5.4 NM and takes place in the Severn River. It is a 3 lap race with pursuit style race. Each boat has a ... Read more