Daily Sailing Cruises

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

Top Rated Tours

Don’t take our word for it—Check us out on Trip Advisor & Yelp.

"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!

October Sailing Schedule

anemptytextlline

Learn More
Special Events Calendar

Special Events

Special Events On Sale Now

anemptytextlline

Learn More
Private Sailing Cruises

Private Sailing Cruises

anemptytextlline

Learn More
Sailing Cruises: October 12-15 from the U.S. Sailboat Show

anemptytextlline

Learn More
Student Cruises

anemptytextlline

Learn More

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 🌅