Sunset Sail with Dirty Secret

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

Sunset Sail with Mike & Kelly Lange

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

Mike and Kelly Lange are a husband and wife ukulele duo.  Lifelong boaters, Mike & Kelly sing original and classic material, some with a maritime theme and some with a broader reach. Mike has played thousands of gigs in the mid-Atlantic and a handful overseas during the past several decades. Over the years he has ... Read more

Old Westminster Winery Dinner Cruise

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

Captain Jen fell in love with this winery's location, wine and people that work at Old Westminster Winery at their grand opening in 2013. 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, where ... Read more

$109.00

Sunset Sail with Ship’s Company

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

Ship's Company is a living history organization dedicated to the preservation of the American maritime heritage. They interpret many aspects of maritime life between 1775 and 1865. For more than a decade, the Ship’s Company Chanteymen have shared sea salts' songs with tens of thousands, all over the East Coast. Aside from being scurvy-free, they ... Read more

Sunset Sail with Eastport Oyster Boys

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

Recognized as the City of Annapolis and the Chesapeake Bay’s Musical Goodwill Ambassadors The Eastport Oyster Boys love to share their musical celebration of life on the shores of the Chesapeake and its scenic rivers with audiences of all ages. For two decades they have educated, amused and delighted thousands with their wit, wisdom and ... Read more

August Wine in the Wind

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

Join us for a three hour sail around the Bay sampling wonderful wines: The Estate of Louis Latour, Burgundy with Timothe Cousins.  This representative from the winery will introduce you to these special wines. 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, ... Read more

$109.00

Sunset Sail with Brandon Hardesty

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

Bumpin Uglies are a polished three piece hailing from Annapolis, MD. Known for their focused approach to not taking life too seriously, Bumpin Uglies have earned a reputation as one of the hardest working bands in the land, constantly touring and perfecting their distinct sound. They also have a knack for poking fun where fun ... Read more

Brunch Sail with Ernie Halter

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

An Intimate, All Ages Acoustic Show with ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Halter has released 6 albums, toured 50 states, and seen his popularity swell to more than 510,000 Twitter followers, 12,000 YouTube subscribers, and nearly 10,000 Facebook 'Likes'. Ernie Halter ... Read more

$89.00

Sunset Sail with Don Shappelle

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

Don Shappelle sings and writes many songs about the Chesapeake bay,it's people,it's boats and the many rivers that flow into the bay.Don grew up on the banks of the mighty Susquehanna River so many of his songs are influenced by that great river. Don also performs sailing and water oriented songs by other artists.Don Shappelle ... Read more

August Lighthouse Cruise

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

Sail 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 soft drinks and snacks, $77 per adult, $50 per child.  Maximum of 35 ... Read more