Cancelled- Private Event Sunset Sail with “The Roadside Show”

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

The Roadside Show is a blue's influenced, roots-rock acoustic band that features music from the turn of the century up to contemporary hits. Bringing over 40-years of musical experience together, The Roadside Show is the latest musical venture of Robert Nolan and Randy Lusk. Both are transplants to this area, having lived from Alaska to ... Read more

$42.00

Sunset Sail with “The Stick Mob”

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

About: Making a little music when we're not busy saving the earth and all that. Biography: We're a bluegrassy, folkin' honky tonk combo from up in them thar mountain hills of Washington DC ... Band Interests: Food, wine Artists We Also Like: Leonard Cohen, Allison Krauss, Steve Earle, Doc Watson, Wailing Jennies "The Stick Mob" ... Read more

Sunset Sail with Bob Sima

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

Bob is a nationally touring singer-songwriter based in Annapolis, Maryland. He burst onto the singer-songwriter circuit by playing in coffee houses, listening rooms, living rooms, and music festivals and by winning slots to perform in major songwriting contests like Kerrville Folk Festival, Mountain Stage, Wildflower, and Falcon Ridge. He has won the hearts of many ... Read more

Sunset Sail with Ken Wenzel

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

Illinois-born Ken Wenzel is a study in contradictions: a guitarist who plays saxophone, a singer who writes instrumentals, a purveyor of restless sentimentality who continues to search for truths best found within. As a singer-songwriter now based in Washington DC, Ken has been gaining attention locally and regionally with his midwestern-accented musings, telling stories spun ... Read more

Schooner Race Watch Cruise

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

Tickets available for sale without lunch included 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 $69 per adult and $40 per child and include bottled water, soft drinks, and snacks. Beer and wine are available for ... Read more

Maryland’s Brewer’s Cup Race

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

Join Heavy Seas and Flying Dog Breweries aboard the Third Annual “Maryland’s Brewer’s Cup”. Buy a ticket aboard your favorite brewery’s boat! During the race, passengers (guest crew) will be able to participate in helping to sail the boat, where appropriate, of course. This will be a “match race” so the competition will be keen ... Read more

September Wine in the Wind – Discovering Tempranillo

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

Join us for a three hour sail around the Bay sampling wonderful wine from Spain. A representative from the wineries will introduce you to these special wines. This will be a relaxing sail including afternoon hors d’oeuvres, soft drinks and four samples of wine. Depart Annapolis at 1:30pm, return at 4:30pm. Price: $99 per person. ... Read more

$99.00

Virginia is for Lovers….of Craft Beer (and Cider)

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

Join us for our first, All Virginia Beer and Cider Tasting on a sunset sail on the 74-foot Schooner Woodwind. Raise the sails, steer the boat or just sit back and relax with four, 4 oz., samples of beer and cider. We will have a representative from the brewery aboard to tell you more about ... 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 two months ago. 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, ... Read more

$99.00

August Wine in the Wind – Stranded on an Island

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

Join us for a three hour sail around the Bay sampling wonderful wine the great wine producing islands, Australia, New Zealand & Sardinia. A representative from the wineries will introduce you to these special wines. This will be a relaxing sail including afternoon hors d’oeuvres, soft drinks and four samples of wine. Depart Annapolis at ... Read more

$99.00