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 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

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

Classic Wooden Boat Regatta

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

Participate in the National Sailing Hall of Fame Classic Wooden Boat Regatta. They have invited the Woodwinds' to participate in the race in the "Spirit of Tradition Class". The course is approximately 5.4 NM and takes place in the Severn River. It is a 3 lap race with pursuit style race. Each boat has a ... Read more

Sunset Sail with “The Stick Mob”

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

Matt 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. The Stick Mob performing on the Woodwind 2014   Band's Website http://www.reverbnation.com/thestickmob Band's Facebook Page https://www.facebook.com/pages/The-Stick-Mob/165403906811064?fref=ts  

Acoustic Brunch with Jay Nash

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

Announcing a Schooner Woodwind exclusive event!  The influences of being on the water, enjoying great food and beverage can create great memories.  However, when you combine those two elements with live music you are now on a journey. We invite you to join us as Captain Jen navigates us out of Annapolis Harbor for a ... Read more

$135.00

Brews in the Breeze Lunch Cruise

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MD

Join the Woodwind crew for an afternoon of beer tasting along with a delicious lunch. 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 ... Read more

$78.00

Annual Great Chesapeake Bay Schooner Race

Watergate Village Annapolis, MD

Be part of the crew aboard the 74-foot Schooner Woodwind on the race down the Chesapeake Bay from Annapolis to Portsmouth, Virginia! Over 45 schooners participate each year. This is a once in a lifetime experience! $900 plus tax per person includes everything. Space for four guest crew members is available.

$900.00

Schooner Race Watch Cruise

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MD

  The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. Tickets* are $83 per adult and $45 per child and include bagged lunch bottled water, soft drinks, and snacks. Beer and wine are available for purchase. *$10 of each ... Read more

$83.00

October Lighthouse Cruise

Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, 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 10:30am, return at 2:30pm, includes bagged lunch, soft drinks and snacks, $93 per adult, $56 per child ... Read more

$93.00