Daily Sailing Cruises

Relax and enjoy the beauty of Annapolis and the Chesapeake Bay.

Top Rated Tours

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"An Annapolis must!"

Custom-Catering-aboard-the-schooner-woodwind

Celebrate on the Chesapeake

Our specialty sailing cruises make any day exceptional. Embark on an unforgettable tour with a carefully crafted menu of food and drink.

SPECIAL EVENTS

Welcome Aboard!

Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland.

Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us!

Make your sailing experience a memorable one! Sail away with us!

Contract of Carriage

Lisa Reed

16:20 17 Jun 22

We had a wonderful trip! The Captain and crew were professional and personable. They shared interesting information about the area and wildlife as we sailed. We saw Ospreys and their nests and Seagulls catching fish. We sailed all the way to the Bay Bridge and went underneath it and between the bridges passing a Princess cruise ship, huge container ships and a coal ship. The weather was incredible and I was sorry to come back to dock. It was a sunset cruise and we also had an almost full moon. I would love to do it again!

Andrew Corl

13:19 03 Oct 22

This cruise was so much fun and relaxing. The Captain and crew were great at getting the passengers involved in operating the boat, hoisting the sails, and steering the boat. Even though it was a cloudy and windy day it was great to be sailing on the bay. Yes we would return again.

Karen Holyfield

21:45 11 Jul 22

I loved the crew! You can't fake personality and true love for what you do. I booked in advance and used the link in the info email to help me find parking since I'm from out of town. We were introduced to the crew and given safety instructions. They explained everything that was going on in sailing terms and layman's terms. I actually got to steer the boat (not well, but...) so the pic attached isn't just a prop! I also got to help hoist a sail! The water was great, the crew was phenomenal and very knowledgeable about the area (Thanks, Sofia, for the best ice cream in Annapolis tip! It was great! Definitely would do this again and again!

Zach Johnson

21:59 08 Aug 22

First time on a sailboat I must say the group that was with us had a blast. Beautiful little cruise with lots of good memories. The crew was very tentative to any needs we had. Definitely would recommend and do it again. Safe travels

Brad Miller

20:58 21 Jul 22

Booked the sunset cruise as part of a birthday gift. We got lucky with perfect weather and a wonderful sunset. The cruise was amazing and the crew was wonderful! We loved the action of seeing the crew maneuver the sails. Their special IPA beer was great too. Highly recommend 👌.

Jessica Jordan

01:23 06 May 23

Woodwind Sailboat Cruises is a top-rated sailing tour company in Annapolis, Maryland that provides an unforgettable experience for guests. One of the standout features of Woodwind is their exceptional communication and expertise, ensuring that each guest feels comfortable and informed throughout the entire experience.From booking the tour to boarding the sailboat, the Woodwind staff is helpful and knowledgeable, providing guests with all the information they need to know about the tour and the area.The sailboat itself is a beautiful vessel, well-maintained and spacious, with plenty of seating and a great sound system for guests to enjoy. The views of the Annapolis harbor and the Chesapeake Bay are absolutely stunning, providing a great backdrop for photos and creating a relaxing and serene atmosphere.Woodwind Sailboat Cruises is also a perfect activity for bachelorette groups, providing a unique and fun way to celebrate with friends while taking in the beautiful surroundings. The staff is accommodating and can even provide custom packages for groups, making it easy to plan a memorable and special experience.Overall, Woodwind Sailboat Cruises is a top-notch tour company that provides an exceptional experience for guests. With their communication, expertise, and dedication to customer service, they are the perfect choice for anyone looking to explore the Annapolis area by sailboat.

Stephanie Fuller

01:17 07 May 23

Such a fun experience! Went on a Sunday brunch music cruise with many friends and two amazing artists. The crew was friendly and fun. I'd never been on a "sailboat" before, I was nervous. We had the best weather we could have asked for, but I think it would have been great even in rain or cold or hot.

Cheyenne Mills

14:55 16 May 23

Had a fantastic time! The crew was awesome! I highly recommend Mondays because they typically don't sell out and u get extra room! The crew interacts with you and asks if anyone would like to help raise the sails or would like to steer! I highly recommend this tour!

Y. K.

13:35 15 Jun 23

My husband and I had a great time on Wednesday night racing tour at Annapolis. It was our first experience with Woodwind tours and we absolutely loved it!

Peggy Smith

14:38 15 Jun 23

Absolutely loved being part of the Regatta races on June 14th, 2023. The Woodwind wins and the crew of the Woodwind were amazing. Thank you for making my husband's birthday so extra special!

Diane Stevens

17:13 27 Jun 23

We went on a Schooner boat ride as part of my fiance's family reunion and had a wonderful time! The captain and all hands on deck were friendly, knowledgeable and took very good care of us. We were worried that we may encounter rain, but the whole 3 hour tour was enjoyable!

Jill Scherling

13:04 24 Jul 23

Phenomenal sunset cruise with Capt. Andy and crew. He was personable and knowledgeable; sharing information about the harbor and the Chesapeake Bay. Saw several boat races going on and our captain explained what would be taking place with each of the boats. Great cocktails on board, too.

Aubrey Winum

12:41 30 Jul 23

We had a great time sailing with Captain Jen! The crew were so friendly & knowledgeable, we even got to help raise the sails and steer the boat! It was a lot of fun seeing the area from water & the experience of sailing. We went on the sunset sail where we were lucky to have a beautiful night!

Timothy White

13:23 03 Aug 23

We went to spend the day in Annapolis and popped by the information station. We inquired about cruises and this one caught our attention. I have done design work on the mansion featured in “Wedding Crashers”. When I heard the schooner was too, I thought serendipitously we must take this boat!We booked in the early afternoon, Tuesday August 1st. The weather was perfect to sail!An added bonus - There Are beer tastings on Tuesday!!Jen and her team were very attentive and made the trip enjoyable.

Harry Rieth

12:58 03 Aug 23

Was a great trip and Capt. Andy, Michael & Nellie were wonderful. They made sure everyone was safe, kept us informed and answered our questions. We couldn't have asked for better weather. Would definitely do it again.

K Stake

15:52 31 Aug 23

We had a wonderful time aboard the Woodwind II. The captain and crew were all very friendly and welcoming. I had trouble finding the check-in location but when I walked to the dock, I was taken care of. We were out for a full 2 hours. Weather was beautiful (which they have no control over.). I would highly recommend this activity.

Jacob B. (Jakeycakes)

13:12 23 Sep 23

Absolutely wonderful experience. Captain Jen and her crew took us for the perfect 2 hour ride and even chased the sunset as it was cloudy until this stunning surprise (see pictures) over Annapolis. Pre-order beers or bubbly to enhance the experience. Be prepared to get a little sea spray and enjoy the ride!

Helen C

22:21 24 Sep 23

Great cruise with really friendly informative crew. Opportunities to assist the crew, on board drinks at reasonable prices and a loyalty programme. We had a great trip out into the bay and were treated to a fantastic sunset 🌅

Ashley Scott

15:07 02 Oct 23

My husband and I went on the mid-day sail at 1:30pm and it was great.In our case, the weather was perfect so there was minimal chop + a nice light breeze made for a great outting. The crew was welcoming and not overly enthusiastic which we preferred. If you have ever been on a Disney cruise or something similar, that "forced fun" and fake enthusiasm is awful. The crew of the Woodwind II were all genuinely enthusiastic and upbeat. Overall it was a pleasant day out on the bay.We learned a lot about the bay and connecting rivers, and meeting others on the boat was an added bonus. We will definitely sail with them again no doubt.(There is a restroom on board if you were panicking about your bladders capacity)

Chris Jensen

17:42 14 Apr 24

The absolute best way to see and appreciate Annapolis. The crew is professional and fun; the schooner is beautiful. We go whenever we have guests in town. Yesterday was the first sail of the season and the wind was howling -- no better place to enjoy it than on the Woodwind.

Kelsey Stout

19:50 14 Apr 24

The opening day of sailing was incredible with schooner woodwind! Had a great time from start to finish - captains and crew were kind, welcoming, and involved the guests in the experience hands on! I will definitely go again and recommend this tour!

Georgij Nikonov

12:27 02 Oct 22

Highly recommend this experience for not only those visiting the area, but locals who are entertaining their guests and are seeking something else other than a boring crowded museum. This is my third time doing this, and it’s simply magical! Crew is entertaining, captain is highly knowledgeable about the area and the bay, history, etc. They have really good beer selection on deck. I do want to try wine tasting cruise as well! Again, a super fun way to spend the evening!

Steve Smalley

18:47 23 May 24

The weather wasn’t fabulous, but being out on the water cruising under an overcast sky was still great. The Captain made everyone feel welcome and a useful part of the crew. No big winds, but a delightful cruise around the bay and into the evening.

Jessica

15:29 20 May 24

Schooner Woodwind Sailing Cruises proved to be the ultimate venue for our bachelorette escapade. As we boarded, the friendly crew welcomed us with warm smiles and a great sense of excitement. The spacious deck accommodated our party with ease, allowing us to mingle, eat, drink and soak in the beauty of the ocean.The ability to purchase drinks on board added an extra touch of indulgence to our experience. They offered a great variety of beers, wine, champagne and other drinks. One free non-alcoholic beverage was offered with every ticket.We had the opportunity to steer the boat and capture some great pictures. The Woodwind crew went above and beyond to capture our memories. Moreover, the smooth sailing conditions made for a comfortable and enjoyable ride.Overall, our experience with Schooner Woodwind Sailing Cruises exceeded all expectations, providing the perfect blend of adventure, relaxation, and celebration. For any group seeking a memorable outing in Annapolis, a sailing cruise with Woodwind is an absolute must.

Karl Hanson

13:10 28 May 24

This was a great experience. I would highly recommend this activity. The captain and crew were great! The ride was smooth. The boat is SLICK n SICK!

Vickie SD

12:39 03 Jun 24

Taking a ride on a sailboat was an experience we wanted to take on our mother/daughter getaway to Annapolis. The weather was perfect for this adventure being sunny, bright and clear. Captain Delaney and crew were accommodating, helpful and provided us with information about the area and the sailboat. Passengers were able to assist with hoisting the sails and steering if they wanted. Our ride left Annapolis waterfront and sailed out to the Chesapeake Bay Bridge. It was the highlight of our weekend!

Victoria Connell

20:29 02 Jun 24

I had a wonderful time! The crew - Captain Delaney, Andrew and Sophia - were super relaxed but obviously knew what they were doing and ran the whole operation like pros which allowed me to relax. The boat was in excellent condition, either very new or just very well maintained. Had a fabulous two hours out on the water. My only suggestion would be seat cushions of some kind to make our bums a little comfier while we’re relaxing.

Amy Tilow

11:25 01 Jul 24

Visiting our friend, Gus, in DC, he made plans for us to sail. So grateful he did!!The experience was amazing! From the land crew (Thanks Joe!) to the ship crew (Sophia and Michael) this team was on their game! Captain Jen made things fun by encouraging folks to participate with hoisting sails and taking the helm! It's been more than 20 years since I did that, I loved every minute!! Also enjoyed hearing of Jen's Atlantic excursion!! Awesome!!We had gorgeous weather with good wind pushing us along!We will definitely be back for more adventures at Sea!!Sails up!Amy and Ralph TilowCleveland, OH

Ed Dillon

09:47 01 Jul 24

We had a great time! Great views, great crew and captain (Jen). 10 out of 10 would come back again if we're ever in the area!! Thank you for the great family memories!!!

Amelia Halsted

14:21 09 Jul 24

This boat was recommended by a local. We travel to Maryland for lacrosse tournaments and are always looking for things to do with free time.We wanted to get on the water during a hot afternoon and even my grouchy teenager had a great time! Highly recommend, we will be back next time we are near Annapolis!!

Elizabeth Preston

16:01 11 Jul 24

A friend and I decided to take cruise in hopes to beat the heat and had a great time! Purchased our tickets online and arrived at suggested time. We lucked out as there was nice wind which resulted in a “sporty” sail! The crew were entertaining and knowledgeable - they all contributed to a great time!

Snofroman Snofroman

22:26 18 Jul 24

Had a great sail on a Thursday afternoon 4:00-6:00 pm. Captain Andy and mates Andrew and Sophia were great. All spent appropriate time chatting with passengers. Very competent/knowledgeable but also very relaxed. Our cruise calm and relaxing with moderate wind. We made it close to Bay Bridge. Everyone got a chance to steer and to raise a sail as it was not crowded. The price was very fair for 2 hours on the water. The boat was in excellent shape. I would happily do again!

Bjorn Guintu

15:34 27 Jul 24

First time sailing and it was a great experience! Great crew and glad they cap the number of folks on the boat where they do as we had ample space on deck. I recommend booking immediately as dates open up (7 day window) as spots fill up quickly.

Marcelo Pinheiro

15:34 04 Aug 24

Great boat. Great route. Great crew and captain. Fun all around! A must do in Annapolis.

Joelle Smith

22:44 04 Aug 24

Captain Andy's experience on the water was second to none! A storm was threatening to come in but we were all excited for the sailing trip. Captain Andy and his crew made sure our safety came first but we all had a great time on the water even though mother nature had her own plans. He constantly checked the weather and radar while we rode amazing winds in the sails across the Chesapeake. It was a beautiful evening, even had our 9 year old daughter in on the fun hoisting the staysail! The crew had us docking just as the clouds opened up with rain. Their experience and expertise on the water was remarkable!! Super fun time even though the weather didn't fully cooperate. Highly recommend this company and especially Captain Andy and his crew!! AMAZING TRIP!!

Ryan Carr

14:25 07 Aug 24

Had an amazing trip and the crew was great! The captain assured all passengers were safe, but also enjoyed their voyage through the bay! I did the sunset beer tasting cruise with my wife, and it was an awesome experience. I would definitely recommend this as part of your trip to Annapolis!

Eric C. Hinderberger

14:15 23 Aug 24

Highly recommend ⭐️⭐️⭐️⭐️⭐️Sailing on the Schooner Woodwind was an unforgettable experience! The crew was incredibly professional and friendly, making sure everyone on board was comfortable and engaged throughout the trip. The schooner itself is beautifully maintained, and there's nothing like the feeling of the wind in your hair as you cruise the Chesapeake Bay.The views were breathtaking, and the crew shared fascinating stories about the area and sailing in general. Whether you're a seasoned sailor or a first-timer, this is an experience you won’t want to miss. I especially loved the chance to help raise the sails—such a cool hands-on moment!Highly recommend this adventure to anyone looking to experience the beauty of Annapolis from the water. Can't wait to sail with them again!

Steven Ackerson

21:10 09 Sep 24

The Woodwind never disappoints, especially the sunset cruise on a warm late summer night. As an Annapolis resident, I always recommend a trip on the Woodwind for visiting family and friends. Great crew, views, and brews.

Amy Diaczenko

21:03 17 Sep 24

We did the sunset sailing tour this past Sunday. Captain Jen and her crew were very knowledgeable and courteous. The boat and sunset cruise were beautiful.

Jennifer Homer

15:17 23 Sep 24

We had an amazing experience on our sunset sailing cruise. It is a great way to see downtown Annapolis from the water. It was a slow cruise with beverages served. The crew was great and even allowed a few passengers to steer the sailboat. We would do this again in a heartbeat!

Kirsten Cordial

20:58 29 Sep 24

ALWAYS an awesome time. My third trip! Absolutely amazing when they cut those engines and you just hear/see the sails and the water close enough to touch. A complete de-stressor. Crew is always amazing and fun. Definitely a MUST DO in Annapolis! Can’t want to go back next year!

Mark Engel

21:45 19 Oct 24

Amazing crew and wonderful sail. Weather was wonderful and while the wind was low we still enjoyed being out on the water. Great way to experience Annapolis.

nicholle la vann

14:18 21 Oct 24

An exhilarating experience out on the Chesapeake Bay. Witnessing a woman captain on the water was inspiring to say the least. Big Kudos to Jenn and her kind crew that served cold refreshments like the tasty white wine to quench your thirst. The bay was live with the Navy doing their training and folks out on their sailboats having a good time in October. Just the type of Sunday cruising needed in life today with so much going on in the world it was a break well needed. The excursion allows you to steer and assist with the sails, from tacking to raising the sails it is truly a memorable ride. Meeting people from out of town from New Zealand and Maine were an added plus while sailing on the Schooner Windward.