Annapolis Sailing Cruises: Schooner Woodwind

Address: 80 Compromise St., Annapolis, MD 21401

Phone: (410) 263-1981 | Presenter

Things to Do | Tours

About Annapolis Sailing Cruises: Schooner Woodwind

Sail the Chesapeake on one of two, 74-foot wooden, schooners that offer a real Chesapeake Bay sailing experience for 2-hour public cruises, as well as longer specialty cruises. Sail past the US Naval Academy, gorgeous homes, and the historic city skyline. Raise the sails, steer the boat, or simply sit back and relax with a cold beverage. During the weeknights, we have History Mondays, Beer Tasting Tuesdays, Wednesday Night Match Racing, and Thursday Local Music Cruises. We have a cash bar filled with local craft beer and wine. Certified for 48 passengers on each schooner. Departs from the downtown Annapolis Waterfront Hotel.

Attraction

General

- Family Friendly

- Maximum Group:

96.00

- Minimum Group:

- Reservation Recommended

Onsite

- Alcohol Served

- Box Lunch Available

- Group Tours Available

- Private Tours Available

- Restrooms Onsite


General

Pricing

- Payment Methods Accepted

American Express, Discover, Master Card, Visa,

TripAdvisor® Traveller Reviews

Wonderful way to see the Bay
What a wonderful way to see the Bay when you don't own a sailboat. We thoroughly enjoyed our sail. The captain and crew of Woodwind were relaxed, knowledgeable of the area, and very friendly. The... Read Full Review
Great way to see the Bay
This was our second trip on the woodwind. We took the 11:00 sail before it got too hot. This is a great way to sail the Chesapeake the old fashioned way. Everyone got an opportunity to steer the... Read Full Review
Great No Matter What The Weather
It rained for about an hour before our "sunset cruise" and was still sprinkling when we boarded the Woodwind. The captain quickly got us out to better weather and a beautiful sail. We sailed all... Read Full Review

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Brews in the Breeze Lunch Cruise
Schooner Woodwind

Brews in the Breeze Lunch Cruise

October 15, 2017

Sail on a lunchtime cruise of beer tasting on the Chesapeake Bay. 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 $84 per adult and include lunch, four 6 oz. beers, and unlimited soda and water. Additional beer will be available for purchase.  Departs  Annapolis City Marina at 11:00 am and returns at 1:30 pm. Maximum 35 guests.

Schooner Race Watch
Schooner Woodwind

Schooner Race Watch

October 12, 2017

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 $86 per adult and $48 per child and include bagged lunch bottled water, soft drinks, and snacks. Beer and wine are available for purchase. *$10 of each ticket purchased will be donated to the Great Chesapeake Bay Schooner Race, a non-profit organization that races to save the Bay in conjunction with the Chesapeake Bay Foundation. Due to US Power Boat Show this event departs from Annapolis City Marina

Brews in the Breeze Lunch Cruise
Schooner Woodwind

Brews in the Breeze Lunch Cruise

October 8, 2017

Sail on a lunchtime cruise of beer tasting on the Chesapeake Bay. 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 $84 per adult and include lunch, four 6 oz. beers, and unlimited soda and water. Additional beer will be available for purchase.  Departs  Annapolis City Marina at 11:00 am and returns at 1:30 pm. Maximum 35 guests.

Classic Wooden Boat Regtta
Schooner Woodwind

Classic Wooden Boat Regtta

September 17, 2017

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 rating, and by the rating they will get a start time. The pursuit style race challenges the competitors to sail through the other race boats to win the regatta. This will be an amazing trip for photography (hint B&W or sepia tone) of these old, gorgeous boats. This is going to be a fun, challenging race! Join the crew! Departs Annapolis Waterfront Hotel Dock at 11:00 am and returns to Annapolis Waterfront Hotel Dock at 2:30pm.  Ticket Price includes gourmet bagged lunch, soft drinks and bottled water and tax.  Our cash bar includes a selection of Craft Beer, Wine & Bubbly!

Black Ankle Winery Dinner Cruise
Schooner Woodwind

Black Ankle Winery Dinner Cruise

September 10, 2017

Captain 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 rolling hills, rocky, low-fertility soils, regular breezes, sunshine and rain to be the home of some truly delicious wines — wines that express the land in which they are grown, enhance the food they accompany, and most important of all are a joy to drink. Estate Winery: “In pursuit of making great wine, we are fully committed to being an estate winery – every grape for every bottle of wine that we produce is grown on our farm and always has been.  The quality of a wine is determined first and foremost by the quality of the grapes that go into it, so we take our farming very seriously. (OK, that is just a nice way of saying that we are control freaks – we admit it).” Sustainability: “We are also big believers in making use of the resources that we have and taking care of those resources so they will continue to be available down the road.  To that end, we spend a great deal of time doing what we think of as farming the soil – making sure that the microbial life in the soil has a good mix of air, water and nutrients so it can create a healthy environment for our vines.” Schooner Woodwind’s Dinner Cruises are a very casual affair. Courses are served picnic-style and food is presented chilled or at room temperature. You will thoroughly enjoy the event aboard. We really do sail, so wear soft soled shoes. And please, feel free to raise the sails, steer the boat, or sit back and relax. Departs from Annapolis at 5:30pm and return at 8:00pm.  Tickets are $109 per adult and include dinner and taxes, four 5-ounce wine pours, soda and water. Maximum 35 guests.  Menu to be Determined.

Wine Tasting Sailing Cruise
Schooner Woodwind

Wine Tasting Sailing Cruise

August 27, 2017

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines.  The 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, perfectly paired bite (we call them magnificent morsels) to go with each wine.   Includes a take-home, boat friendly, wine glass by Go Vino with the Woodwind’s logo on it. Raise the sails, steer the boat or sit back and relax with your wine and food. Depart Annapolis at 4:00 pm, return at 6:00 pm. Price: $79 per person. Maximum 40 guests.

Wednesday Night Race Series on board Schooner Woodwind
Schooner Woodwind

Wednesday Night Race Series on board Schooner Woodwind

May 17, 2017

Woodwind and Woodwind II will be match racing every Wednesday night that there is an Annapolis Yacht Club (AYC) Race. Both boats will start on the AYC starting line at 6:45pm, and then race out to a slightly different race course, probably a little longer. During the race, passengers (“guest crew”) will be able to participate in helping to sail the boat and steer the boat, when appropriate of course. This will be America’s Cup-style racing since it is match racing, so the competition will be very strong between the father and daughter teams who are the captains of each Woodwind.