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

An Annapolis Must!
I've done this twice now in my two visits to Annapolis. Enjoyed a beautiful sunset sail both times. In July, the boat was full, but everyone had a place to sit. In October, there was plenty of... Read Full Review
Trip on a tall masted schooner
Beautiful afternoon trip on one of two tall masted schooners. The crew were very fun and professional. They took us out on the bay for about an hour and a half. Very family friendly event... Read Full Review
Overcrowded Mess
As stated in other reviews the boats are overcrowded, to the point they feel unsafe at times. If you are near the end of the line you will get stuck in the middle of the boat, below the advertising... 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. 

Father’s Day Brunch Sailing Cruise
Schooner Woodwind

Father’s Day Brunch Sailing Cruise

June 18, 2017

Our Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00am and returns at 1:00pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food:  $90 per person, $50 per child. Maximum 35 guests.

Wine Tasting Sailing Cruise
Schooner Woodwind

Wine Tasting Sailing Cruise

June 4, 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.

Acoustic Brunch Sail with Gareth Asher

Acoustic Brunch Sail with Gareth Asher

May 29, 2017

An Intimate, Acoustic Show with GARETH ASHER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. As a touring artist, Asher has shared the stage with Shawn Mullins, Glen Phillips(o/ Toad the Wet Sprocket), Emerson Hart, Angie Aparo, Corey Smith, Sister Hazel, Collective Soul, 3 Doors Down, Steve Cropper and many more. Born in the small town Bowdon, GA, Gareth Asher was raised on a steady diet of old school funk, rock and soul. Asher attributes many of his musical sensibilities to monumental artists like Stevie Wonder, Phil Collins, and groups like Chicago. As a writer, he respects the work of iconic performing songwriters like Jackson Browne, Otis Redding, and Don Henley and The Eagles. “I feel like my shell is finally cracking, and the best songs are starting to emerge. All my inner most thoughts and emotions are breaking through to the surface, and insisting on a ray of light to shine down upon them”, says Asher. “Gareth has a wonderful way of singing to your soul”, says Captain Jen, “add that while sailing on the Chesapeake and you have the perfect moments that will turn into favorite memories. Don’t miss this show!” Check out a video of Gareth performing aboard Schooner Woodwind. 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 40 guests will be able to enjoy this really special event!

Blue Angels Cruise
Schooner Woodwind

Blue Angels Cruise

May 24, 2017

Watch the famous Blue Angels do their aero-acrobatics while sailing on the Bay. Tickets include box lunch, soda $103 per person, $66 per child with child's lunch. Maximum 40 guests.

Blue Angels Practice Cruise
Schooner Woodwind

Blue Angels Practice Cruise

May 23, 2017

Watch the Blue Angels practice their aero-acrobatics during this special cruise. Depart from Annapolis at 11:00am and return at 3:30pm. Advanced ticket purchase required, includes box lunch, soda and snacks; $103 per person, $66 per child w/ child's lunch. Maximum 40 guests.

Wine Tasting Sailing Cruise
Schooner Woodwind

Wine Tasting Sailing Cruise

May 21, 2017

Taste these wonderful wines while sailing around the Chesapeake Bay. This relaxing cruise includes four samples of wine each paired with a magnificent hors d’oeuvres morsel.  We will  have a representative from the wineries aboard to discuss the selected wines. Cruise departs from the Annapolis Marriott Waterfront Hotel at 4pm and returns at 6pm. Tickets are $79/adult, maximum 35 guests.

Wednesday Night Race Series
Schooner Woodwind

Wednesday Night Race Series

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.

Sunset Sails & Beer Tasting with Port City Brewery
Schooner Woodwind

Sunset Sails & Beer Tasting with Port City Brewery

May 16, 2017

Sunset Sails & Beer Tasting, aboard a 74-foot, classic wooden schooner, Woodwind. We feel that everyone should be able to enjoy great, craft beer while sailing on the Chesapeake Bay. And on every Tuesday’s sunset sail, we feature 3 beers from a regional micro-brewery. A brewery representative comes aboard and educates in a very casual manner about beer. Port City Brewing Company is proud to revive, celebrate and continue this rich brewing history in our modern artisanal brewery right outside our nation’s capital. We started the brewery in January 2011 because we found that the DC area needed more choices for great quality, locally produced craft beer. We are committed to producing world class quality beers without compromise for the DC and Mid Atlantic market. The historic port city of Alexandria, VA has a proud tradition of brewing beer for the region that dates back to the 19th century. Founded in 1866, the Robert Portner Brewing Company operated in Alexandria for almost 50 years. It grew to become the largest brewery in the southern United States, and was Alexandria’s largest employer. The company thrived until 1915, when Prohibition came to Virginia, and the brewery went out of business. Our mission is to be a reliable and innovative regional brewer of top quality beers that are delicious and well balanced, made from the finest ingredients available, and which celebrate their raw materials.

Mother's Day Brunch Sailing Cruise
Schooner Woodwind

Mother's Day Brunch Sailing Cruise

May 14, 2017

Our Mother’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00am and returns at 1:00pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food:  $90 per person, $50 per child. Maximum 35 guests.

Lighthouses of the Chesapeake Bay Sailing Cruise
Schooner Woodwind

Lighthouses of the Chesapeake Bay Sailing Cruise

May 7, 2017

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 10:30am, return at 2:30pm includes bagged lunch, soft drinks and snacks, $93 per person, $56 per child with child’s bagged lunch. Maximum of 35 guests.

Sunset Sails & Acoustic Music
Schooner Woodwind

Sunset Sails & Acoustic Music

May 4, 2017

Sit back and relax as different local musicians entertain you while sailing on the Chesapeake Bay. The Singer/Songwriter genre will be well represented as they play acoustically aboard the Woodwind - See more at: http://www.schoonerwoodwind.com/public-sailing-cruises-annapolis-maryland/sunset-sailing-on-the-chesapeake-bay/#sthash.c3Q1nLl2.dpuf

Sunset Sails & Beer Tasting with Port City Brewery
Schooner Woodwind

Sunset Sails & Beer Tasting with Port City Brewery

May 2, 2017

Sunset Sails & Beer Tasting, aboard a 74-foot, classic wooden schooner, Woodwind. We feel that everyone should be able to enjoy great, craft beer while sailing on the Chesapeake Bay. And on every Tuesday’s sunset sail, we feature 3 beers from a regional micro-brewery. A brewery representative comes aboard and educates in a very casual manner about beer. Port City Brewing Company is proud to revive, celebrate and continue this rich brewing history in our modern artisanal brewery right outside our nation’s capital. We started the brewery in January 2011 because we found that the DC area needed more choices for great quality, locally produced craft beer. We are committed to producing world class quality beers without compromise for the DC and Mid Atlantic market. The historic port city of Alexandria, VA has a proud tradition of brewing beer for the region that dates back to the 19th century. Founded in 1866, the Robert Portner Brewing Company operated in Alexandria for almost 50 years. It grew to become the largest brewery in the southern United States, and was Alexandria’s largest employer. The company thrived until 1915, when Prohibition came to Virginia, and the brewery went out of business. Our mission is to be a reliable and innovative regional brewer of top quality beers that are delicious and well balanced, made from the finest ingredients available, and which celebrate their raw materials.

Sailor’s Delight Cocktail Sailing Cruise
Schooner Woodwind

Sailor’s Delight Cocktail Sailing Cruise

April 29, 2017

Sail away on one of our first sunset sails of the season. Enjoy great appetizers, cocktails, wine and beer as we enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, three drink vouchers and a sunset sail from 5:30pm-7:30pm. Menu will be announced soon. Cruise departs from the Annapolis Waterfront Hotel and tickets are $74/adult with a maximum of 35 guests.

Sailor’s Delight Cocktail Sailing Cruise
Schooner Woodwind

Sailor’s Delight Cocktail Sailing Cruise

April 28, 2017

Sail away on one of our first sunset sails of the season. Enjoy great appetizers, cocktails, wine and beer as we enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, three drink vouchers and a sunset sail from 5:30pm-7:30pm. Menu will be announced soon. Cruise departs from the Annapolis Waterfront Hotel and tickets are $74/adult with a maximum of 35 guests.

Wednesday Night Race Series
Schooner Woodwind

Wednesday Night Race Series

April 26, 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.