Things to Do Boating

Annapolis Sailing Cruises: Schooner Woodwind

80 Compromise St., Annapolis, MD 21401
(410) 263-7837
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About Annapolis Sailing Cruises: Schooner Woodwind

Sail the Chesapeake on a 74-foot schooner! Raise the sails, steer the boat, or sit back and relax on a two-hour sail. Special, longer event cruises, too. The Woodwind and Woodwind II offer a real Chesapeake sailing experience for public sails and private events. Buy a ticket, or privately rent the entire boat. Fun, team match racing, corporate outings, crab feasts and catered sunset sails. Sailing is a great way to celebrate birthdays, reunions, and a wedding weekend. 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,

October Lighthouse Cruise
Annapolis City Marina

October Lighthouse Cruise

October 14, 2018

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 10:30 am, return at 2:30 pm, includes bagged lunch, soft drinks, and snacks, $96 per adult, $58 per child with child’s lunch. Maximum of 35 guests. Scroll down to see menu choices. Cruise Departs from Annapolis City Marina (Boat Shows are in town)

Schooner Race Watch
Annapolis City Marina

Schooner Race Watch

October 11, 2018

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. 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! They will be racing to the Norfolk area, we will cheer them on till it’s time to go in. We will be under sail with the schooners (and yes you’ll be sailing on one too). We will not cross the starting line, but we will be sailing around them all as they come down from Baltimore. Includes Lunch. Tickets* are $89 per adult and $50 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
Annapolis Sailing Cruises: Schooner Woodwind

Brews In The Breeze Lunch Cruise

October 7, 2018

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 $86 per adult and include lunch, four 6 oz. beers, and unlimited soda and water. Additional beer will be available for purchase.  Departs  Annapolis at 11:00 am and returns at 1:30 pm. Maximum 35 guests.

September ~ Wine in the Wind
Annapolis Sailing Cruises: Schooner Woodwind

September ~ Wine in the Wind

September 23, 2018

Join us for a two-hour sail around the Chesapeake Bay while sampling wonderful wines from TBD.  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 (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. You will be able to raise the sails, steer the boat or just sit back and relax with your wine and food. Depart Annapolis at 4:00 pm, return at 6:00 pm. Maximum 40 Guests

Wednesday Night Races
Annapolis Sailing Cruises: Schooner Woodwind

Wednesday Night Races

May 16, 2018

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.