Everything Local Dinner Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDEnjoy our “Everything Local” themed dinner and drinks while under full sail on the Chesapeake Bay. This cruise will focus on food that you can purchase locally or grow yourself. Local wines from Black Ankle Vineyards of Frederick County, specifically their Gruner Vetliner (white) and Rolling Hills (red) will pair nicely with the menu. ... Read more
August 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 bagged lunch, soft drinks and snacks, $89 per adult, $56 per child ... Read more
Photography Workshop
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDPHOTO WORKSHOP aboard the 74-foot, classic wooden sailing schooner, Woodwind The Sail: If you are looking for a great evening of sailing and photography think about our new Photo Workshop on the Woodwind. The “Woodwind” is a two-masted, 74- foot schooner that sails out of Annapolis. Just sailing on this wooden schooner is a great ... Read more
Sunset Sail with Deanna Dove
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDFrom a tiny peninsula called Broomes Island off the Patuxent River grew the local legend, Deanna Dove, Island Girl. Deanna Dove's original songs are stories from her life, whose own history is deeply rooted as a young crabber on Island Creek. Deanna's musical style shows deep influences of rock, pop, alt-country, blues and gospel while ... Read more
August Wine in the Wind – Stranded on an Island
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a three hour sail around the Bay sampling wonderful wine the great wine producing islands, Australia, New Zealand & Sardinia. 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 ... Read more
Old Westminster Winery Dinner Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCaptain Jen fell in love with this winery's location, wine and people that work at Old Westminster Winery at their grand opening two months ago. The proprietors, the Baker family, are raising a reputation for crafting wines of intrigue. The property is situated on a rocky plot of ground just south of historic Westminster, MD, ... Read more
Virginia is for Lovers….of Craft Beer (and Cider)
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for our first, All Virginia Beer and Cider Tasting on a sunset sail on the 74-foot Schooner Woodwind. Raise the sails, steer the boat or just sit back and relax with four, 4 oz., samples of beer and cider. We will have a representative from the brewery aboard to tell you more about ... Read more
September Wine in the Wind – Discovering Tempranillo
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a three hour sail around the Bay sampling wonderful wine from Spain. 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 1:30pm, return at 4:30pm. Price: $99 per person. ... Read more
Maryland’s Brewer’s Cup Race
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin Heavy Seas and Flying Dog Breweries aboard the Third Annual “Maryland’s Brewer’s Cup”. Buy a ticket aboard your favorite brewery’s boat! During the race, passengers (guest crew) will be able to participate in helping to sail the boat, where appropriate, of course. This will be a “match race” so the competition will be keen ... 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, $89 per adult, $56 per child ... Read more