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 

History Monday Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

History Monday Sunset Sail

June 18, 2018

Sunset Sails & History, aboard a 74-foot, classic wooden schooner, Woodwind. Legends and Lore of the Annapolis Waterfront by Dave Gendell Dave brings aboard and entertaining and compelling set of stories and insights around  Annapolis history, the Naval Academy, the sailing scene, and the personalities that make Annapolis one of the world’s most unique waterfront communities. 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. www.schoonerwoodwind.com   410-263-7837   .

Father's Day Brunch Sail
Annapolis Sailing Cruises: Schooner Woodwind

Father's Day Brunch Sail

June 17, 2018

Our Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. The sailing cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, bacon & swiss quiche squares, blackened salmon with cusabi sauce served with hearty bread, grilled flank steak, fresh fruit salad, orange juice and homemade biscotti. $92 per person, $52 per child. Maximum 35 guests.

Local Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Local Music Sunset Sail

June 14, 2018

Enjoy music performed by Mike & Kelly Lange during a two-hour sunset cruise aboard the 74-foot Schooner Woodwind. Mike and Kelly Lange are a husband and wife ukulele duo.  Lifelong boaters, Mike & Kelly sing original and classic material, some with a maritime theme and some with a broader reach.  Mike has played thousands of gigs in the mid-Atlantic and a handful overseas during the past several decades. Over the years he has performed with many popular bands in the Baltimore/Washington area both as a bandleader, member, and freelance musician. His original music has been featured on numerous radio stations in the mid-Atlantic area including WRNR, WPFW, WTMD, and WHFS as well as many independent radio stations overseas.  Mike is best known for performing with the Eastport Oyster Boys, Tiki Barbarians, and Boogie Express bands. Known as an accomplished pianist, Mike plays ukulele and melodica on the Woodwind. Having spent years performing in choirs and plays, Kelly is well known for her beautiful voice and tasteful strumming on her mango tenor ukulele. 

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

History Monday Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

History Monday Sunset Sail

June 11, 2018

Sunset Sails & History, aboard a 74-foot, classic wooden schooner, Woodwind. The Life of Frederick Douglass with William Ridgley. Frederick Douglass was described as a living counter-example that blacks we’re ignorant and unable to learn to read or write. Come learn how his everyday life was as a slave and how he was able to escape slavery.  Born in Baltimore, raised in Annapolis, William grew up in Downtown Annapolis. He graduated Annapolis Senior High in 1989 and joined the Marine Corps. He served during Operation Desert Storm (92) and Operation Groundhog (Mogadishu, Somalia; 93-94) and after his discharge, he lived in Southern California for about ten years and returned to Annapolis in 2005. He is an avid history student working on his bachelor’s degree. And he is also a reenactor and tour guide, and co-owner of Annapolis Colonial Tours and a rookie Boatsman.  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. www.schoonerwoodwind.com   410-263-7837   .

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

June ~ Wine in the Wind

June 10, 2018

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines. A representative from the Tommasi Family Estates 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. Cruise departs from the Annapolis Waterfront Hotel at 4:00pm, returning at 6:00pm. Tickets are $81/adult maximum 40 guests.  www.schoonerwoodwind.com   410-263-7837 Buy Tickets Now https://schoonerwoodwind.zaui.net/modules/webBooking/index.php?action=Details&activityDate=1528603200&id=1311

Local Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Local Music Sunset Sail

June 7, 2018

During our 25th Anniversary Celebration Week, we invite you to join us for a special sunset sail to enjoy music performed by Crab Alley Lite during a two-hour sunset cruise aboard the 74-foot Schooner Woodwind. They were one of the first bands to play on the Woodwind 25 years ago. Crab Alley founders Jeff Holland and Janie Meneely will join up for a Woodwind cruise and regale the crew with their original songs of the Bay and beyond. Serious or saucy, their songs shed light on recreational boating as well as Chesapeake traditions here on the Bay. 

Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Beer Tasting Sunset Sail

June 5, 2018

During our 25th Anniversary Celebration Week, we invite you to join us for a special sunset sail with Hugh Sisson from Heavy Seas Brewery as he talks about how the craft beer industry has changed in Maryland in the past 25 years. Come reminisce with us and sample 3 beers from Heavy Seas Brewery while enjoying the beautiful sunset under full sail on our 74-foot schooner

History Monday Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

History Monday Sunset Sail

June 5, 2018

Sunset Sails & History, aboard a 74-foot, classic wooden schooner, Woodwind. During our 25th Anniversary Celebration Week, we invite you to join us for a special sunset sail with John Scarano and Ken Kaye as they discuss the History of the Schooner Woodwind~ From Dream to Reality. 25 years ago, Ken, Ellen, and Jennifer Kaye had a dream realized with the building of the Schooner Woodwind at the Scarano Boat Yard, the second schooner that Scarano built. Listen to the Naval Architect and Designer of the boats talk with Ken Kaye about how they decided upon the hull design, sail plan, functionality and proportions of the Woodwind.  John Scarano will talk about the beginning days of his family’s boatyard, and how it has grown to build more and more certified USCG vessels for entrepreneurs across the country.  This will be the first time since Woodwind II was finished, that they will be in a relaxed atmosphere to reminisce about the dreams they both had 25 years ago and where they are now. Cruises depart from the Annapolis Waterfront Hotel at 6:30pm and returns 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

May 31, 2018

Enjoy music performed by The Eastport Oyster Boys during a two-hour sunset cruise aboard the  74-foot Schooner Woodwind. Recognized as the City of Annapolis and the Chesapeake Bay’s Musical Goodwill Ambassadors The Eastport Oyster Boys love to share their musical celebration of life on the shores of the Chesapeake and its scenic rivers with audiences of all ages. For two decades they have educated, amused and delighted thousands with their wit, wisdom and a special message of stewardship and appreciation for the Bay and its unique maritime culture and history. Anyone who loves being on or near the water will find they have a lot in common with these guys, whose simple philosophy is wrapped up in the three basic necessities of life “a good hat, a good dog, and a good boat!” Though calling the waterman’s village of the Maritime Republic of Eastport home, their songs and stories ring true to any of the Chesapeake’s harbor towns, rivers or quiet coves and have been appreciated as far as the shores of Nova Scotia, Ireland, Europe and Australia. The Boy’s spirit and music have also been featured in numerous national and international radio, television, print, and film productions. The Eastport Oyster Boys entertain with a wide variety of musical styles that include island rhythms, boogie-woogie, dixie-swing, maritime chanteys, waltzes and even some good ol’ rock-and-roll. So come aboard and get ready for a fun time with The Eastport Oyster Boys. The crabs are hot and as we say here on the Bay “Ain’t the beer cold!  

Acoustic Brunch with Music by Ink & Ash
Annapolis Sailing Cruises: Schooner Woodwind

Acoustic Brunch with Music by Ink & Ash

May 28, 2018

An Intimate, Acoustic Show with Ink + Ash (feat. Gareth Asher + Nicki Thrailkill) aboard the Schooner Woodwind for a concert on a beautiful schooner, including a light delicious brunch on Memorial Day.  Band’s BIO: In this life, we spend our days in blissful ignorance as to what lies ahead. We work, we play, we dream, we live. In this chain of every day, there is sometimes a beginning, like any other, that is fated to hold within it a moment forever life-altering, and sometimes life feeding. March 18th, 2011 was the day Nicki Thrailkill and Gareth Asher’s worlds collided. Two souls met under a full moon’s sky, on the same patch of earth, in the same blink in time. Two souls – discovering in each other someone to keep safe and sound throughout this adventure of living. On the second day, they wrote about it; breathing into existence the musical manifestation of love and wonder; pouring from their hearts to yours the magic that lies deep beneath the skin and bones of us all, waiting to be released. This music is like a raw, uncut stone with hidden magic. Hold it in your hands, your hearts, your souls. Feel the vibration and be healed. Captain Jen: You will love this music!  Back by popular demand, they are returning for another Memorial Day Sail. Many of the guests aboard were introduced to their music a couple of years ago, and make this cruise every year. Join the fun, and sit back and relax. 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 37 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. Cruise departs from the Annapolis Waterfront Hotel at 10:30am and returns at 1:00pm.  Adults $86.www.schoonerwoodwind.com   410-263-7837  Buy Tickets Now https://schoonerwoodwind.zaui.net/modules/webBooking/index.php?action=Details&activityDate=1527480000&id=155

History Monday Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

History Monday Sunset Sail

May 28, 2018

Sunset Sails & History, aboard a 74-foot, classic wooden schooner, Woodwind. with Tom Guay speaking on Tales and Tunes of the Golden Age of Annapolis. Enjoy a historically guided 2 hour sunset sailing cruise.   You will enjoy tunes and tales of life during the Golden Age of Annapolis; the balls, the theater, the songs, the social season, which abruptly ended, forever, with the burning of the Peggy Stewart in 1774.  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. Beer and wine are available for purchase. www.schoonerwoodwind.com   410-263-7837 .

Local Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Local Music Sunset Sail

May 24, 2018

Enjoy music performed by Don Shappelle during a two-hour sunset cruise aboard the 74-foot Schooner Woodwind.  Don Shappelle sings and writes many songs about the Chesapeake Bay, it’s people, it’s boats and the many rivers that flow into the bay. Don grew up on the banks of the mighty Susquehanna River so many of his songs are influenced by that great river. Don also performs sailing and water oriented songs by other artists. Don Shappelle accompanies his songs on 6 & 12 string guitar and harmonica. He has performed up and down the Chesapeake Bay in many settings over the years and counts singing onboard the Woodwind as one of his favorites.

Blue Angels Show Cruise - SOLD OUT
Annapolis Sailing Cruises: Schooner Woodwind

Blue Angels Show Cruise - SOLD OUT

May 23, 2018

Watch the Blue Angels perform their aero-acrobatics during this special cruise. Depart from Annapolis at 11:30 am and return at 3:30 pm. Typically, we sail for a 2-hour cruise and then we anchor up front in the “spectator zone” for the best view of the performance which usually happens around 2:00 pm. Advanced ticket purchase required, includes box lunch, soda, and snacks; $106 per person, $68 per child w/child’s lunch. Maximum 40 guests.  SOLD OUT

History Monday Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

History Monday Sunset Sail

May 21, 2018

Sunset Sails & History, aboard a 74-foot, classic wooden schooner, Woodwind. with Mechelle Kerns speaking on Forts on the Chesapeake. An overview of the military forts located in the Chesapeake Bay including those related to Annapolis and Baltimore. USNA was established in 1845 but the Yard was once an Army installation called Fort Severn with two forts constructed between 1807 and 1811. Dr. Mechelle Kerns is a Historical Archaeologist and History Professor (USNA and UMUC). She specializes in topics related to Colonial America and maritime history. 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. Beer and wine are available for purchase. www.schoonerwoodwind.com   410-263-7837 .

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.

Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Beer Tasting Sunset Sail

May 15, 2018

Sample beer from DC Brau Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. When co-founders Brandon Skall and Jeff Hancock opened the doors to their brewery in 2011 on Bladensburg Road in NE Washington, DC Brau Brewing Company became the first packaging brewery in the District of Columbia since 1956.  DC Brau’s signature brews include: The Public (Pale Ale), The Corruption (IPA), The Citizen (Belgian-style Ale), Brau Pils (German-style Pilsner), and Penn Quarter Porter (Robust Porter), with seasonal and special brews available throughout the year including the award-winning On the Wings of Armageddon (Double IPA). For more information on DC Brau, visit http://www.dcbrau.com, and follow on social media @dcbrau