Latest Past Events
Rum Running on the Bay
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, AnnapolisCelebrate 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
Brunch Sail with Jesse Ruben
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, AnnapolisAn 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
Saturday Night Sailor’s Delight Cocktail Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, AnnapolisSail 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