US Sailboat Show Cruises – Sunday
US Sailboat Show Dock F2 80 Compromise Street, Annapolis, MD"Woodwind" sails up to four times daily on 90 minute cruises from temporary docks throughout the Sailboat Show October 5th - 9th from Dock "F2". Combo-Ticket Deal! Save up to a 40% discount off your ticket into the Boat Show by buying a 90 minute schooner cruise combined with your Sailboat Show Ticket. What is ... Read more
Brews in the Breeze Lunch Cruise
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDSail on a lunchtime cruise of beer tasting on the Chesapeake Bay. 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 $84 per adult ... Read more
US Sailboat Show Cruises – Monday
US Sailboat Show Dock F2 80 Compromise Street, Annapolis, MD"Woodwind" sails up to four times daily on 90 minute cruises from temporary docks throughout the Sailboat Show October 5th - 9th from Dock "F2". Combo-Ticket Deal! Save up to a 40% discount off your ticket into the Boat Show by buying a 90 minute schooner cruise combined with your Sailboat Show Ticket. What is ... Read more
Schooner Race Watch Cruise
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDThe Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. There will be up to 25 plus schooners at the starting line. Seven of them are at least near 100+ feet. This is going to be incredible. Join the fun! ... Read more
October Lighthouse Cruise
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, 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 10:30am, return at 2:30pm, includes bagged lunch, soft drinks and snacks, $93 per adult, $56 per child ... Read more
Dogfish Head Brews in the Breeze Brunch Cruise
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDWho says you can't have beer for breakfast? Sail on a brunch-time cruise featuring Dogfish Head Brews on the Chesapeake Bay. After we raise all our sails, a fun, Dogfish Head brewery representative will introduce you to the beer line up for the day which will pair well with our delicious pre-plated, 2 course brunch. ... 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 5:30 pm, return at 7:30 pm. Tickets are $76 per adult with a maximum of ... 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 5:30 pm, return at 7:30 pm. Tickets are $76 per adult with a maximum of ... Read more
Brunch Sail with Jesse Ruben
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAn 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
Rum Running on the Bay
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCelebrate the History of Rum with the unique experience of Rum Running on the Bay. Join us for a two and a half hour sunset sail on the Bay, while learning about rum, prohibition, sailing, food pairing, cocktail making and so much more! During Prohibition (1920 to 1933) it was illegal to consume alcohol in ... Read more