164 Reviews
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Toni Banket
· September 19, 2016
I totally disagree with John's experience below. We had a spectacular time. Captain and crew were extremely pleasant and professional. When signing up for t...his adventure/experience you know you will be on a group boat outing. It is not a private sail therefore you do need to plan. Regardless of your seat preference when leaving dock, you can and we did move about the boat during sail. We were fortunate enough to board the boat that had music - local musicians join for the sail. Very nice touch. Likewise, the crew was wonderful. They took photos when requested, shared stories about the waterway, highlighted key points, shared the weekly schedule of events aboard the Woodwind. For the price point, it is a well worth adventure to take in a sunset, see Annapolis from the waterfront vs. from land and enjoy the serenity of the Cheasapeake. See More
John Perceful
· September 17, 2016
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 a...dvertising tarp, with no breeze. The captain and crew do not seem to care that everyone has an enjoyable experience. Hated every bit of this experience. Would not recommend this company to anyone. See More
Lindsay Reilley Roark
· September 10, 2016
Booked tickets 3 days prior to a 530 cruise. From working at Pussers for years, I knew the sunset cruises can get crowded, so planned to be there 30 minutes pri...or. A usual 10 minute ride took 40 minutes after some kind of crazy car accident. I called them and told them we were doing everything we could to get there. They were polite on the phone. Literally ran from our car at 535 to see the boat sailing away. No refunds no exchanges. They called back, which I appreciate (hence the 2 stars), however I do not think buying tickets in advance is worth the risk as they will not accommodate. See More
Sherry Snyder Evans
· September 18, 2016
It was a Beautiful day yesterday for a Sailboat Cruise. It was amazing, relaxing and beautiful. The staff was spectacular, informative and fun.
I got to put one of the Sails up and Play Captain manning the wheel. Great Fun!
Thank you again for a marvelous time.
Reggie Mark Stout
· August 16, 2016
I got it! We were not feeling real positive heading out to sail around and then watch the fireworks on a rainy overcast day. Oh, it wasn't raining by fireworks ...time, and that was nice, but OMG! Skimming across the Severn and the bay with wind and rain pelting my face was the best fun I've had since...well...we won't talk about that. I had a BLAST. See More
Fran Gurkin
· October 24, 2016
We had a wonderful time on the cruise and the crew couldn't have been nicer and more accommodating. They made sure everyone had opportunities to participate! Captain Mickey and his crew were by far, the best!
Howie Hoffman
· August 7, 2016
Captain Jenn is the best! We did the sunset cruise and B&B for our 33rd anniversary! Couldn't ask for a better sailing experience. Looking forward to going back!
Barney La Prad
· November 10, 2016
Jon and I were married on the Woodwind II on September 11, 1999. We had the most lovely time with family and friends.... 17 years of honeymooning going strong
Bethany Roberts
· August 27, 2016
Beautiful boats and the crew were all extremely helpful and knowledgeable. Great sight-seeing tour that I would highly recommend!
Dan Fowler
· June 23, 2016
The Schooner Woodwind Races are definitely the Best thing going on Wednesday Nights in Annapolis! They are awesome boats with a great crew. There is nothing like the power of a Big Schooner cruising the wind on the Chesapeake!
Maria Elena
· October 30, 2016
Espectacular!! Amazing experience. Captain and crew were very friendly and helpful!!
Pete Carrico
· September 25, 2016
It's always a pleasure to see Woodwind I and II gracing the water with their elegance.
Melissa Blanchard Arroyo
· May 8, 2014
We had a fabulous time this evening on the Woodwind II for our sunset cruise. This is our 3rd time sailing with you all and Captain Mickey and his crew made it ...very memorable for my two kids. Despite the older crowd, he made sure my kids had an experience they will not soon forget. My son Ben will be talking about how he got to Captain the boat for a long time. :)
Thanks once again for everything and we are looking forward to our next sail with you all. :)
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Jack Irons
· September 7, 2016
We had a great time. Would do it again if given the chance.
Linda Bagby Gilmer
· June 23, 2014
Fantastic Crew! Fantastic Schooner! Fantastic Cruise We had a blast Tuesday (6-16) with the Flying Dog Beer tastings. This was a Father's day gift, one we'll ne...ver forget!!! We'll be back for sure! If you are in the area this is a must do experience... Worth every dollar and before or after... enjoy a bite to eat at the only on the waterfront eatery in Annapolis, next door at the Marriott... You'll be glad you did this excursion on the Woodwind ! See More
Vicki Windham
· August 10, 2016
It was a fun and information filled sailboat ride. The crew was very helpful and polite. We saw many sights of Annapolis from the boat.
Ryan Saunders
· August 28, 2015
Mothers Day weekend 2015
Light winds . A glass (bottle) of wine . Great crew . A bottle of wine.
Left the dock at the Marriott (Pussers) mid day. Skies wer...e beautiful. Once out beyond the noise of motorboats,you really get a sense if how life was on the Chesepeake the quiet movement under sail really gave me I different perspective on what life was like
Quite romantic even
With so many different sailing experiences you can have Schooner Woodwind. There is something for everyone
My 10 yr old son , wife and I really enjoyed the trip under the bay bridge . The trip really made for a great others Day Weekend
Highly recommend it
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Clint Davis
· July 26, 2016
This is a quality operation with seasoned professionals providing an excellent sailing experience, particularly for group events.
Laura Kelter
· September 19, 2016
Captain Jen was so fun, crew was great. Will return.
Jane Townsend
· August 31, 2016
Lovely cruise around the harbor. Crew was very helpful.
Sailing on the Schooner Woodwind
Launching of Woodwind 3-31-14
Sailing on the Woodwinds on 4th of July Weekend!

Fun day interacting with kids at the Maritime Career Fair. Favorite line, "thanks for teaching me how to tie a square knot, now I know how to fix my shoelaces when they break."

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A reminder join us at the 7th Annual Marine and Maritime Career Fair, Saturday, Feb 25 from Noon to 3:00 pm at Annapolis High School
FREE for All Students (Grades 6 - 12+)…/maritime-ca…/2017-career-fair

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Thanks Pride of Baltimore II for the reminder of this great shot when Schooner Woodwind: Annapolis Sailing Cruises found you on the Bay and chased you down. What great memories. So warm today, we all feel like sailing!

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Pride of Baltimore II with Palle Christensen and Schooner Woodwind: Annapolis Sailing Cruises.

Is it sailing season yet? @schoonerwoodwind #allwoodallgood 📷Phil Wieser

Love, Love, Love all of our FB Friends! Wishing you all a wonderful Valentine's Day. #valentinesday #lovesailing

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Check it out, we are now on Instagram. Follow us @schoonerwoodwind #springiscoming


Finishing up projects on the Woodwinds! Cabin tops got brand new anti-skid paint.

Know of any middle school, high school or college kids that might want to explore a job or career in the Marine Industry? Check this Career Fair out on Saturday, February 25 at Annapolis High School. (We will be there, too!)…/maritime-ca…/2017-career-fair
Schooner Woodwind: Annapolis Sailing Cruises added 5 new photos to the album: Bottom Painting Party — with Bill Malachowski at Bert Jabin Yacht Yard.
January 25

It's so warm out that our professional maintenance team can get a coat of bottom paint on!

Great tips, and an added surprise! Check out the article. Thanks, Travel Addicts!

One of our favorite things about travel is taking photographs. We're always trying to do it better and have put together a list of some of the things we've learned along the way.

By keeping just 15 travel photography tips in mind, even the most amateur of photographer can capture great images.|By Travel Addicts

Road Trip Masters came to Annapolis last summer and had fun checking out our amazing town! Congrats to Captain Andy Barton and the crew aboard that day for a job well done. The full length version will be re-aired in April and broadcasted nationally.

Enjoy this short version of Road Trip Masters, a half hour TV show that airs on Discovery's "Destination America" channel. Experience the Road Tripper's jour...

Congratulations to the Skipjack Stanley Norman- 115 Years Old! With our awesome maintenance team, we are making sure the Woodwinds can go past 115 years old. Think about all the stories that boat has! Wow.

Built in 1902 in Salisbury, Maryland, the Stanley Norman, is a single-masted, Bay-built sailing vessel designed to harvest oysters with a pair of dredges that are dragged across the bottom of the Bay. The Chesapeake Bay Foundation acquired the Stanley Norman to play a unique and active role as CBF's...

Updated- we are now SOLD OUT! Tickets are going fast!! As of right now we have 11 tickets left for all of our Blue Angels cruises for May.…/blue-angels-performance-…/

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 p...
Sail aboard two identical, wooden 74-foot schooners that sail out of Annapolis, Maryland. Public Cruise or Private Events can be arranged.
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