Everything Local Dinner Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDEnjoy 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, Light House Bistro, prides themselves on getting produce, meats, and many other ingredients from the local area. For our wonderful selection of alcoholic ... Read more
August Wine in the Wind
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDJoin us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from South America. 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, ... Read more
Black Ankle Vineyards Dinner Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDCaptain 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 O'Herron (that's us). They believe that the central Maryland Piedmont, sitting at the foothills of the Appalachian Mountains, has the right mix of ... Read more
Classic Wooden Boat Regatta
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDReduced 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 Classic Wooden Boat Regatta. The Woodwinds' have been ... Read more
Brunch Sail with Ernie Halter
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDAn 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
Cocktail Cruising
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDSail away with great appetizers, cocktails, wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, two drink vouchers and a sunset sail. Depart Annapolis at 4:30pm, return at 6:30pm. Tickets are $78 per adult with a maximum of 35 guests. Cocktail Cruise Menu: Black Bean Hummus Poblano Pimento Cheese Served with ... Read more
October Lighthouse Cruise
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDReduced 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. Sail to as many as three different lighthouses on the Chesapeake ... Read more
Acoustic Evening Sail with Tyrone Wells
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDSchooner Woodwind is pleased to announce the return of TYRONE WELLS to perform aboard the boat for an Intimate, Acoustic Show. We will cruise to a secluded cove for the performance and then enjoy a sunset sail back to the dock. This will be Tyrone's fourth time singing and sailing on the Woodwind. It all ... Read more
Brews in the Breeze Lunch Cruise
Schooner Woodwind at the Annapolis City Marina Dock 410 Severn Ave, Annapolis, MDReduced Ticket Price - not including 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. Sail on a lunchtime cruise on the Chesapeake Bay. Tickets are $69 ... Read more
Schooner Race Watch Cruise
Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MDThe Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. There will be up to 25 plus schooners at the starting line. Seven of them are at least near 100+ feet. This is going to be incredible. Join the fun! ... Read more