Sailabration Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSAIL to Sailabration in Baltimore for an all day adventure!: We will set sail from Annapolis at 8:00 am, sail towards Baltimore and rendezvous with the Tall Ship fleet by 11:30 near Fort McHenry. We will return to Annapolis no later than 5:00 pm. Included is: breakfast, lunch, afternoon happy hour hors d'oeuvres and a glass ... Read more
Brews in the Breeze Lunch Cruise
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, 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 served buffet style while sailing on the beautiful Bay! Tickets are $74 per adult ... Read more
Acoustic Evening Sail with Tyrone Wells
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDSchooner Woodwind is pleased to announce the return of TYRONE WELLS to perform aboard the boat for an Intimate, Acoustic Show. This will be Tyrone's third time singing and sailing on the Woodwind. It all started in 2007 when Captain Jen fell in love with his music and asked if they wanted to go sailing ... Read more
Wedding Crashers 10th Anniversary Brunch Sail
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCan you believe its been 10 years? Enjoy a movie themed brunch and 2 adult beverages. Join Captain Jen as she tells tales about the filming of the movie and share your favorite memories of this cult classic. Food includes crab cakes (of course), meatloaf & egg sliders, scallops wrapped in bacon and other fun themed items. ... Read more
Champagne Brunch
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDJoin the Woodwind crew for the most festive brunch on the Bay! Enjoy a very “bubbly” beverage selection, including sparkling wine, and two other champagne cocktails accompanied by delicious food and always entertaining company! (Includes 3 Drink Vouchers for Bubbly, Beer or Cocktails.) Food Menu: Sweet Pepper, Mushroom and Parsley Egg Frittata w/ green ... Read more
Port City Beer Tasting Paired with Oysters
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a 2-hour sail tasting four delicious beers from Port City Brewing Company paired with outstanding oysters from the Chesapeake Bay. A brewery representative will be on hand to teach how to taste beer in addition to what you are tasting with the oysters. Brad from War Shore Oysters will be on hand to talk about how he farms ... Read more
Friday Night Sailor’s Delight Cocktail Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail 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 5:30pm, return at 7:30pm. Tickets are $61 per adult with a maximum of 35 guests. ... Read more
Saturday Night Sailor’s Delight Cocktail Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDSail 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 5:30pm, return at 7:30pm. Tickets are $61 per adult with a maximum of 35 guests. ... Read more
Mother’s Day Brunch
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDOur Mother’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. $88 per person, ... Read more
May Lighthouse Cruise
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 Annapolis at 11:30am, return at 3:30pm includes soft drinks and snacks, $77 per person, $50 per child. Maximum of 35 ... Read more