Sunset Sail with Dirk Schwenk

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

Dirk Schwenk is an award winning singer-songwriter from the great state of Maryland. His formal training includes years of clarinet and symphonic band, but he found rock and roll as a late-addition bass player in the High School talent show, and never went back. He has been singing, playing guitar and songwriting ever since, and ... Read more

Everything Local Dinner Cruise

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

Enjoy our “Everything Local” themed dinner and drinks while under full sail on the Chesapeake Bay. This cruise will focus on food that you can grow yourself or purchase locally.  Our caterer, Palate Pleasers, prides themselves on getting produce, meats, and many other ingredients from the local area.  For our wonderful selection of alcoholic beverages ... Read more

$109.00

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

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. Ernie Halter will play acoustically while at anchor in a secluded cove. He will play for over an hour and after the performance we will set sail on the 74-foot, ... Read more

$89.00

Sunset Sail with Ken Wenzel

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

With the release of  “…Beneath Potomac Skies”  -  a 12-song, full-band collection of moments and memories culled from time spent in Washington DC, and many other locales – singer/songwriter/saxophonist Ken Francis Wenzel is eager to introduce his own roots-rock, country jazz-tinged take on love, learning, and life in contemporary America. Featuring several guest appearances from ... Read more

Sunset Sail with Matt Bednarsky

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

His unique style draws influence from a variety of genres including pop/rock, folk, jazz, and blues. Think somewhere in between James Taylor and John Mayer with Ryan Adams and Michael Bublé mixed in. Born to a jazz guitarist and music teacher father and a mother with a classical pedigree, Matt grew up in Shelton, CT ... Read more

Dodon Vineyards Wine Dinner

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

Established in 2007, the vineyards at Dodon are fortuitously situated on rolling hills just south of Davidsonville, Maryland. When they began their first experiments with 150 vines, the goal was clear: to practice sustainable agriculture and produce exceptional wines. As ninth generation custodians of this historic farmland, and as demanding winemakers, they are committed to using ... Read more

$109.00

Solar Eclipse Cruise

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

Due to popular demand the first boat has sold out and we have opened a second boat for this event. Both boats are now sold out Sail away and watch the event being called the "Great American Eclipse".   While we are not in the area that will see the total eclipse, Annapolis is in the ... Read more

$54.00

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

August Wine in the Wind

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

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from Spain.  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 paired bite ... Read more

$79.00