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

Amazing ride, amazing crew!
This is my second time riding on the Schooner Woodwind. I came previously on a bachelorette party, and enjoyed myself in both settings. The crew is accommodating and informative. The views are... Read Full Review
Amazing Ride!
My wife and I recently went on Woodwind for the sunset cruise and boat and breakfast. The sunset cruise was amazing, the staff was amazing, and the view of Annapolis from the boats path was... Read Full Review
Warm sunny Sunday in Annapolis with the chance to be casually on the water
Perfect chance to stay cool and see the sights without doing the work. If you are a sailor this is a kiddie ride. If you are a sightseer it is only 2 hours but packed with much fun. Read Full Review

© TripAdvisor 2015

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.

Brunch Sail Cruise with Ernie Halter
Schooner Woodwind

Brunch Sail Cruise with Ernie Halter

August 6, 2017

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, classic wooden schooner, Woodwind. Raise the sails, steer the boat, sit back, relax and meet Ernie while sailing the Bay. Enjoy a light brunch as we cruise to a secluded cove, including Apple Cake, Bacon & Swiss and Artichoke with Red Pepper Quiche Squares and a refreshing fruit salad. Mimosas and Bloody Marys will be available at our cash bar filled with local craft beer and wine. A maximum of 35 guests will be able to enjoy this really special event! We do sail rain or shine. If the musicians cannot play due to the weather, but we can still sail- we will refund the performance part of the ticket.  There are no assigned seats. There are no refunds or exchanges unless the captain cancels the cruise due to unsafe conditions.

Everything Local Dinner Cruise
Schooner Woodwind

Everything Local Dinner Cruise

July 30, 2017

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 purchase locally or grow yourself. Tickets are $109 per adult and include three course dinner, 3 drink vouchers, and unlimited soda & water. Maximum 35 guests. Black Ankle Vineyards will be aboard showcasing 2 of their favorite wines. Blackwater Distillery in Kent Island will be showcasing one of their spirits in a unique cocktail aboard.

Firework Cruise on Schooner Woodwind
Schooner Woodwind

Firework Cruise on Schooner Woodwind

July 4, 2017

Join us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Marriott dock at 6:30pm for a sunset sail with live entertainment by “Ship’s Company”. We will then anchor close to the fireworks barge for the 9:15pm fireworks display and return to the dock after the show. Tickets are $89 per adult, $62 per child and include bottled water, soft drinks, and a wide selection of desserts. Beer and wine will be available for purchase. Maximum 40 guests. 

Sailing Cruise with live music aboard the Schooner Woodwind
Schooner Woodwind

Sailing Cruise with live music aboard the Schooner Woodwind

June 29, 2017

Enjoy music performed by Dirk Schwenk during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. 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 has played for crowds at many of Maryland’s best venues, including the Rams Head on Stage, the Recher Theater, Rams Head Live, The 8×10 and Annapolis’ The Whiskey.  Set lists start with great original music but could include everything from Johnny Cash to Jack Johnson to the Ramones.   Great songs; drinking songs with a Country edge; and a good time while we are here on earth.  For Woodwind Cruises, you can count a few good old sailing songs as well. This event will be a return to Dirk’s roots: he was married aboard the Woodwind in August, 1995.  Cruise departs from the Annapolis Waterfront Hotel at 6:30pm and returns at 8:30pm. Tickets are $46/adult, $29/child under 12 yrs. and include a soft drink and snack. Beer and wine are available for purchase.  www.schoonerwoodwind.com   410-263-7837

“Sail Away” and the history of the Chesapeake Bay aboard Schooner Woodwind
Schooner Woodwind

“Sail Away” and the history of the Chesapeake Bay aboard Schooner Woodwind

June 26, 2017

History Cruise: Eating, Drinking and Making Merry in Colonial Annapolis with Diane Rey. Set sail with Anne Catharine Green,Annapolis’ 18th century Printer to the Province, a woman far ahead of her time; to discover the kinds of activities that helped makeAnnapolis the “Athens of America” during its golden age. Learn about early tavern life, sought-after imports, the “clubbical behavior” of the celebrated Tuesday Club, and the whirlwind that was Annapolis’ social season, as drawn from the pages of Mrs. Green’s newspaper, the Maryland Gazette. Enjoy your craft beer while hearing about the strange concoctions that Colonials quaffed!  Cruises depart from the Annapolis Waterfront Hotel at 6:30pm and return at 8:30pm. Tickets are $46/adult, $44 seniors 60+, $29/child under 12 yrs. and include a soft drink and snack.  www.schoonerwoodwind.com    410-263-7837

Sunset Sails & Beer Tasting with Jailbreak Brewery
Schooner Woodwind

Sunset Sails & Beer Tasting with Jailbreak Brewery

June 6, 2017

Sample beer from Jailbreak Brewery while enjoying the beautiful sunset under full sail. We are a production craft brewery located in Laurel, Maryland and proud residents of Howard County. Beginning in 2013 with original founders Justin Bonner and Kasey Turner and becoming fully operational in 2014, our artfully crafted beer is meant to be an escape from whatever drama is present in your life. We are made up of professionals from various industries all brought together by the common desire to make something different and do something with our lives that has more purpose. Our beers only use fresh ingredients, never substituting with artificial flavors or extracts, and are also Kosher certified. Some of our core beers include Feed the Monkey (Orange Hefeweizen), Czech the Technique (Czech Pilsner), The Infinite (Amber Ale), Poor Righteous (American IPA), and Big Punisher (Double IPA).

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.