Classic Wooden Boat Regatta
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDReduced Ticket Price - not including Bagged Lunch (the order has already been placed with our caterer). Be sure to bring your own lunch to enjoy aboard. Lunch must be self contained (boxed or bagged) - no buffets or displays will be allowed aboard. Participate in the National Sailing Hall of Fame Classic Wooden Boat ... Read more
Sunset Sail with Deanna Dove
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDDeanna Dove is best known as the “Island Girl” in her hometown for her compositional writing style about her lifelong experiences on the Chesapeake Bay. She has earned a loyal audience for her ability to craft songs that include elements of rock, pop, blues, alt-country and gospel into a distinctly individual style with a universal ... Read more
Sunset Sail with Don Shappelle and Don Sennett
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDDon Shappelle is a singer/songwriter and guitarist who grew up on the banks of the mighty Susquehanna River and sings about the people,history and boats of the Chesapeake bay and it's many beautiful rivers. Sailing songs and sing-alongs are part of Don's repertoire and always get an audience involved. Performing with Don Shappelle is bassist ... Read more
Brunch Sail with Michael Tolcher
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAn Intimate, All Ages Acoustic Show with MICHAEL TOLCHER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Michael Tolcher will play acoustically while at anchor in a secluded cove. He will play for about an hour and after the performance we will set sail on the 74-foot, classic wooden ... Read more
Brunch Cruise with Jay Nash and special guest, Natalia Zukerman
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAn Intimate, All Ages Acoustic Show with JAY NASH and special guest, NATALIA ZUKERMAN aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Jay Nash will play acoustically while at anchor in a secluded cove. He will play for about an hour and after the performance we will ... Read more
US Sailboat Show Cruises – Thursday (VIP/Preview Day)
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
US Sailboat Show Cruises – Friday
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
US Sailboat Show Cruises – Saturday
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
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