Sunset Sail with Stefan Heuer Music

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Stefan 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

Sunset Sail with “The Shatners Unplugged”

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

We'll be stripping down many of the dance tunes played in The Shatners band while adding songs from  artists like Boston, Amy Winehouse, and the Bodeans for an eclectic variety of music to share. We'll even throw in an original or 2 if those aboard are feelin' it! We are thrilled to be part of ... Read more

Black Ankle Winery Dinner Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Due to popular demand, the first boat for this event has sold out... Update- At 9:00pm, now both boats are sold out. Captain Jen fell in love with this winery's location, wine and people that work at Black Ankle Winery. Black Ankle Vineyards is the culmination of a long-time dream of founders Ed Boyce and Sarah ... Read more

$109.00

Sunset Sail with Dirty Secret – CANCELLED DUE TO PRIVATE CHARTER

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Dirty 'Little' Secret is the lively acoustic side of local area favorite, Dirty Secret. With a variety of old school classic rock, blues, and a little country - there's something for every music lover! http://www.dirtysecretblues.com/ https://www.facebook.com/pages/Dirty-Secret

$46.00

Classic Wooden Boat Regatta

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Reduced 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, MD

Deanna 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, MD

Don 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, MD

An 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

$92.00

Brunch Cruise with Jay Nash and special guest, Natalia Zukerman

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

An 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

$99.00

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