Sunset Sail with Tony Lucca
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAn Intimate, Acoustic Show with TONY LUCCA aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including delicious light appetizers. Tony Lucca captured America’s hearts last year as the Team Adam finalist on NBC’s hit TV show “The Voice.” The fans of the Schooner Woodwind knew he would do well since his ... Read more
Mother’s Day Brunch – 10am departure
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDThis event has sold out. Due to popular demand we have added a second event departing at 11am. Please see Mother's Day Brunch - 11am departure for more information.
Mother’s Day Brunch – 11am departure
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJust added due to popular demand! Our Mother’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 11:00am and returns at 2:00pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, quiche lorraine squares, baked citrus salmon with hearty bread, grilled flank steak, fresh fruit salad, orange juice ... Read more
Lighthouse Cruise – May 21st
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail 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 from Annapolis at 11:00am and return at 3:30pm. Advanced ticket purchase required, soda, and snacks; $79 per person, $51 ... Read more
June Wine in the Wind – Tuscany, Kissed by the Sun
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a three hour sail around the Bay sampling wonderful wines from Tuscan region of Italy. A representative from the wineries will introduce you to these special wines. This will be a relaxing sail including afternoon hors d’oeuvres, soft drinks and four samples of wine. Depart Annapolis at 2:00pm, return at 5:00pm. Price: ... Read more
Take Dad Sailing
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a family friendly 2-hour cruise where Dad (and mom and kids, etc) can kick back and relax on the Chesapeake Bay while celebrating under sail!! Get your tickets now to take Dad sailing on Father's Day! Depart Annapolis for a two-hour cruise at 11:00 am or 1:30pm. Cruise comes with a free ... Read more
Father’s Day Brunch
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDOur Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00am and returns at 1:00pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, quiche lorraine squares, baked citrus salmon with hearty bread, grilled flank steak, fresh fruit salad, orange juice and homemade biscotti. $86 per person, ... Read more
Brews in the Breeze Lunch Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin the Woodwind crew for an afternoon of beer tasting along with a delicious lunch. After we raise all our sails, we will start the tasting with the lightest of the four beers. Lunch will consist of all your Chesapeake favorites, including crab cakes, served buffet style while sailing on the beautiful Bay! Tickets are ... Read more
Independence Day Sailing
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDMake your plans early for sailing on the 4th of July! Tickets are now available for all daytime sails on July 4th. Go sailing during the day and then stake out your spot on land to watch the Fireworks over Annapolis Harbor. Depart Annapolis for a two-hour cruise at 11:00 am, 1:30pm or 4:00pm. Cruise ... Read more
Fireworks Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30pm for a sunset sail with live entertainment by "Ship's Company". We will then anchor close to the fireworks barge for the 9:15pm fireworks display and return to the dock after the show. Tickets ... Read more