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

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

August ~ Wine in the Wind

August 12, 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

Local Everything Dinner Cruise
Annapolis Sailing Cruises: Schooner Woodwind

Local Everything Dinner Cruise

July 29, 2018

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 grow yourself or purchase locally.  Our caterer, Palate Pleasers, prides themselves on getting produce, meats, and many other ingredients from the local area.  For our wonderful selection of alcoholic beverages, we choose independent breweries and distilleries within a 70-mile radius. Menu to be determined Tickets are $111 per adult and include three-course dinner, 3 drink vouchers, and unlimited soda & water. Maximum 35 guests.

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

July ~ Wine in the Wind

July 15, 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

4th of July Fireworks Cruise
Annapolis Sailing Cruises: Schooner Woodwind

4th of July Fireworks Cruise

July 4, 2018

Join us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30 pm for a sunset sail with live entertainment by “Ship’s Company”. We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the show. Tickets are $91 per adult, $64 per child and include bottled water, soft drinks, and a wide selection of desserts including fresh fruit. Beer and wine will be available for purchase. Maximum 40 guests. 

Local Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Local Music Sunset Sail

June 28, 2018

Enjoy music performed by Deanna Dove during a two-hour sunset cruise aboard the 74-foot Schooner Woodwind.  Deanna Dove is best known as the “Island Girl” in her hometown for her compositional writing style about her lifelong experiences on the Chesapeake Bay. She has earned a loyal audience for her ability to craft songs that include elements of rock, pop, blues, alt-country, and gospel into a distinctly individual style with a universal appeal. The “Island Girl” has established her reputation as a powerful, earthy singer, guitar playing, beat making, one-woman show.

History Monday Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

History Monday Sunset Sail

June 25, 2018

Sunset Sails & History, aboard a 74-foot, classic wooden schooner, Woodwind. The Key to Annapolis History, by Jeff Holland.  The Key to Annapolis history lies right there in the harbor. It can’t be found by looking port, and it can’t by looking starboard. It’s only when you drop the hook that the secret can be found when you anchor, you’ll discover that the bottom of the harbor is only 12 feet down! Cruises depart from the Annapolis Waterfront Hotel at 6:30pm and return at 8:30pm. Tickets are $46/adult, $29/child under 12 yrs. and include a soft drink and snack.  www.schoonerwoodwind.com    410-263-7837 .

Local Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Local Music Sunset Sail

June 21, 2018

Enjoy music performed by Kyle Offidani during a two-hour sunset cruise aboard the 74-foot Schooner Woodwind. Born and raised in the bay area of Delaware- Kyle Offidani is a musician and song catcher . Musically- Kyle draws inspiration from World music, Instrumental guitar, Roots, Blues, Soul, and Americana music. When listening to the sounds of Kyle, you will hear echoes of these genres Woven into the tapestry of his songs. Kyle writes with a strong notion of genuinity and vulnerability - believing that openly expressing one's own truth, opens a paradoxical gateway for somebody else to find and express their own. Since 2009 Kyle has toured nationally to share the music that defines his life. His passion for music, travel, and life experiences have paved the way to play acclaimed festivals and venues throughout the United States. In recent years, Kyle planted roots in Nashville, TN and in more recent years Austin, T.X where he soaked up the inspiration and perspective needed to create his upcoming L.P, which is expected to be released into 2018 

Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Beer Tasting Sunset Sail

June 12, 2018

Sample beer from Heavy Seas Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. Beer takes us on adventures. It allows us to discover new flavors and exotic cultures. Our quest for great beer can lead anywhere, from corner pubs to faraway breweries.  For Heavy Seas founder, Hugh Sisson, beer altered the trajectory of his life.  In 1980, intending to become a stage actor and director, Hugh’s plan was to move to NYC after completing his course work for a masters degree in theater. Hugh’s father, Albert, a Baltimore area businessman, persuaded him instead to come “help” at a newly opened family business, a tavern called Sisson’s. When Hugh showed up to start what he assumed would be a short-term position, his father tossed him the keys to the pub, said “OK, don’t f*** up!” and walked out the door

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.