(Private Cruise on Both Boats) Sunset Sail
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD
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
Sunset Sail with Austin Ellis
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSoulful, Engaging, Authentic. Austin Ellis captivates listeners with an enchanting voice and intimate acoustic style. Influenced by the smooth delivery of John Legend and laid back strumming of Jack Johnson, Ellis invites audiences to relax and enjoy the music. Known for his warm and charming live performances, he is well on his way to becoming ... 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
Sunset Sail with Dirty “Little” Secret
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDDirty Secret's founding members, Kelly Secret & Scott O'Toole, explore the acoustic side of blues with a shot of old school rock. They are the perfect pairing with a sunset and a locally brewed Heavy Seas Beer. You have heard of beer pairings with food? How about beer & song pairings? Kelly works at Heavy ... 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