The 5-Day Sailing Adventure Cruise
Portsmouth, VA Portsmouth, VASpend 5 days aboard the Schooner Woodwind sailing from Portsmouth, VA to Annapolis. $1800 plus 10% tax per cabin (double occupancy). Includes accommodations aboard, gourmet meals (4 breakfasts, 5 lunches, and 3 dinners, one dinner is ashore), sail training (if wanted), and absolutely fantastic scenery! Four cabins available. Tickets are not available for purchase online. ... 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 $74 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 $74 per adult with a maximum of ... Read more
Acoustic Sunset Sail with Paul Pfau
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAn Intimate, All Ages Acoustic Show with PAUL PFAU aboard the Schooner Woodwind for a concert on a beautiful sailing boat. Nashville’s Paul Pfau (rhymes with "wow") is a modern-day troubadour, a skilled and eager listener, with a gift for setting the truths of love, life and loss to music. His talent for taking in and re-interpreting ... Read more
Cancelled due to Private Event: Sunset Sail with Matt & Katie (of The Stick Mob)
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDMatt and Katie play with the Stick Mob, a folk-ameri-something-grass-n-stuff quintet from the hillbilly wilds of the nation's capital. They love to play and sing beautiful old melancholy tunes as well foot-stomping originals. Band's Website https://thestickmob.bandcamp.com/ Band's Facebook Page https://www.facebook.com/pages/The-Stick-Mob/165403906811064?fref=ts
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 10:30am, return at 2:30pm, includes soft drinks and snacks, $79 per adult, $52 per child with child’s ... Read more
Sunset Sail with Stefan Heuer Music
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDStefan Heuer is a singer songwriter residing in Annapolis, Maryland. His original music as a solo performer has reached ears all over the world. Stefan performs at venues in Annapolis and around the DMV area. Stefan mirrors elements of folk, but his original music holds a strong foundation of blues and soul. Band's Website ... 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 10:00 am and returns at 1:00 pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, quiche lorraine squares, blackened salmon with cusabi sauce served with hearty bread, grilled flank steak, fresh fruit salad, orange juice and ... 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
May Wine in the Wind
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from the Tuscany Region. The representative from the winery will introduce you to four special wines while we are under sail. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along with each wine is a delicious, perfectly ... Read more