Sunset cruise in the age of Covid-19: a wonderful way to get away from things for a couple hours. Crew was great, the boat is gorgeous, the weather cooperated and there was a beautiful sunset. Highly recommend and will definitely do again - but understand youre on a boat on the WATER so you are probably going to get wet from the spray, its all part of the sailing experience! (If you order a drink stick with something in a can, much easier to drink from/not spill than a glass of wine!) I really liked there being space on the boat/it not being crowded and we didnt have to worry about being too close to other people.

We went out on the Woodwind Schooner II yesterday and we had the most delightful time. The Captain and crew were funny, friendly, and all-business when it came to the operation of that sailboat. It’s a fun time and gives you a taste of all that’s involved in sailing a vessel that size - easily managed with three people who know what they’re doing. Highly recommend.

We enjoyed ourselves greatly. The crew was so friendly and the Captain extremely knowledgeable. It was a great day. We look forward to going back!

Exceptional nice and knowledgeable crew make this one of our highlights this summer. Two full hours of entertainment and sailing enjoyment. We even had a beer tasting experience on board. Highly recommend.

My girlfriend and I had a great trip with this awesome crew. We had took a relaxing 2 hour trip around the Chesapeake bay that was full of education and history. They are open until Halloween so I recommend getting a charter booked asap!

Had the chance to experience a great sail with my wife. She did a story on Schooner and we had an amazing time with the captain and the crew. Out first time in Annapolis and Schooner made it memorable. Highly recommended! Will be coming back again.

Just spent two consecutive days sailing on the Woodwind. Cant say enough about the boat and the crew. Two days of flawless Fall weather did not hurt. Will go again in a heartbeat and plan to do so.

Waited for a rain to stop , so our trip was 1 1/2 hr.. NO wind , I was bored. motoring. The captain was very knowledgeable and experienced. Recommend to try it on a windy day with full sail .

Taking kids on any type of experience like this, especially on the water, can make any parent nervous. Im not talking about safety, though thats certainly a concern (and one that Schooner Woodwind has nailed down). Im talking about the following. Will they behave? Will they get bored? Is there enough for them to do? Is watching the staff sail enough for them? I will say this... my kids were in awe. They sat in our zone for almost the entire duration of our trip without a single complaint. They watched the other boats, waved to other people on the water, spotted osprey and crab cages. They asked questions of the staff and bonded with each other. It was a lovely thing to watch and experience.Watching the teamwork of the staff was awesome, so much so that my oldest even commented on how well they work together. It was a good lesson for my kids, who have practiced sailing together several times since our trip.All in all, our afternoon was magical. A sailing on the Woodwind is a family activity you wont forget, and an afternoon of fun I think we all need. Fun, safe, educational. Does it even get better than that?

We took a large group on a Sunday two hour public cruise. The staff was great. The ticket comes with a free soda/water and snack. They sell craft beer, wine and champagne too. I dont know how to sail and it was cool to see the crew do their thing. Bring sunblock. It gets hot in the summer. Great views and good times.

We had a wonderful experience. Very relaxing and peaceful.

The whole crew does a great job making the most out of the situation. We have sailed with them before, and even with COVID restrictions, they have found a way to make this fun and are not lowering their service quality.We originally had reservations for a fireworks cruise, but when the fireworks were cancelled, we still wanted to go. I had pretty big plans for that night (proposing) and did not want the uncertainty of waiting until the last minute to find out if I could get on. After reaching out to Beth about my plans and the fact that I had been reserved on the original sail for that night, Beth got me approved for a reservation ahead of time. She was in constant communication with me along the way too. She went out of her way to make my plan work, and the final result was a YES.We will be back again...maybe for an anniversary cruise!

First time sailing, and I wasnt sure it will be family friendly. It turned out the crew gave me and my family a wonderful experience. They are very friendly and patient. Captain Jen was great all around. I got to help pull the sail, and my 8 yr old son helped steered the boat. Watching the sail filled with wind and boat quietly cut through the water was such a beautiful experience.

We had an absolutely amazing time sailing aboard the woodwind for the sunset cruise. The captain and crew were all friendly, knowledgeable and fun. The crew encourages volunteers to help raise the sails - so you can get involved if you want. With that said - you by no means need to feel obligated to help. Alcohol is served via cash bar. All and all this is the number 1 thing I recommend to tourist or friends asking for the best way to experience Annapolis.The only way to experience Annapolis is on the water, and the woodwind is the most enjoyable way to do so.(Ide like to put out there that is a review for our 3rd time on the woodwind, all of which were amazing.)

Great experience. Solid crew, beautiful boat, gorgeous weather. Highly recommend. Thanks!

The crew and captain alone make this trip worthwhile, but the entire experience is not to be missed if youre in Annapolis!

Wonderful gift from my brother Phil, of a 2 hr. sail from Annapolis harbor to Bay Bridge n back. Capt. & crew were excellent & very knowledgeable; even to someone who grew up in area.

Captain Mickey & the crew gave us a wonderful experience. Well hopefully do this sail again. Captain Jen was great to work with the night before when the weather didnt cooperate. First rate organization.

I should be up front that I can only comment on the process of scheduling and embarking on a sail; I did not sail on the ship itself.I had a sail set for the weekend of the Annapolis Boat Show, to depart at 5:45 p.m. Unfortunately, during the day of the sail, Annapolis, and all of the Chesapeake area, experienced a severe high tide that caused flooding in and around the area of the Annapolis City Dock. As a result, the Boat Show was canceled early, and when my party arrived around 5:00 p.m., we werent exactly sure where to go.The ticket contained instructions detailing which slip to look for, but as someone who has never been to the Annapolis Dock, it was very difficult for me to figure out where that slip was, as there was no address or directions. It was just US Sail Boat Show - Dock F2. Which would probably have been enough, if anyone from the Boat Show had been able to help us, but they had all already left, or were busy trying the mitigate the flooding.We tried calling Woodwind to clarify where we should be, but no one answered; their ticket office was closed for the weekend, and there were no alternate numbers provided.I decided to check my email, to see if updates had been provided, and Woodwind had in fact sent an email noting the state of the boat show. However, to clarify they only gave vague directions, saying things like the hotel closest to the yacht basin parking lot. As mentioned above, we were not at all familiar with Annapolis, so this could have been any of several buildings, and because large portions of the surrounding streets were flooded or closed off by police, checking on each of them was a difficult prospect. Without going into detail, we gave up trying to find the dock at about 5:50, when we were pretty sure the boat would have already left without us, as the follow-up e-mail explicitly noted that the boat was still sailing.I feel like there was very poor support for this event. I am sure that hosting sails during the Boat Show complicates matters, but at no point in either the original ticket or the follow-up e-mail was sufficient detail given to make things easier. There are no addresses or step-by-step directions, which feels like it would be sort of expected for an event like this. And to boot, there was no way to talk with anyone on the Woodwind team, as their ticket office was closed and no other number listed. I would think that there would be a way to reach someone at the company whenever there is a sail scheduled, to help answer questions and provide information for unforeseen events.Based on the above, I would advise being cautious about sailing on the Woodwind during a special event if you are not an Annapolis native, or at least familiar with the area. Their support was nonexistent, and does not feel like a professional business. I am sure the boat and sail themselves are wonderful, but getting to them, for me at least, was unpleasant and frustrating.

Excellent sailboat tour experience, would highly recommend this to anyone. Great friendly staff, drinks available aboard, cant go wrong!

Another great cruise on Woodwind II. This was the sunset cruise on the Saturday evening of the Annapolis Sailboat Show. The wind was a steady 20 knots and we moved briskly through the bay at 8+ knots. The crew was friendly and knowledgeable as always, and I got my usual turn at the helm. All in all a splendid evening. Ill do it again sooner than later

We had a perfect day for the sunset sail. The staff was great, and the cruise was just lovely. Price is really good, too. Definitely hoping to do this again!

Very relaxing and fun experience. The crew was very engaging and informative. A great time. A shout out to the man selling the tickets who helped this rookie with my ticket purchase. His efforts and kindness will make us return and tell others.

Absolutely amazing two hour trip, great captain and crew, also picked a less busy time to sail, it was relaxing and as perfect as it could be. Must do if visiting Annapolis, these are 74 ft sailing schooners, impeccibly maintained and staffed, what a wonderful experience.

Great time and very competent!

Such a great time as always. Beautiful evening sail, and the crew was awesome.

My second cruise on the Schooner Woodwind was lovely. The crew is always so fun and friendly. It was nice to get a soda/water and bag of snacks included with the cost.

The Boston College alumni from Baltimore, Washington DC and Annapolis had a great time aboard the Woodwind. Capt. Jenn and her crew were fantastic. We will be back!

Wow, I scheduled a boat trip with my girl here. She told me she sailed before to find when we arrived she hadnt. When we went to look at the boat, she didnt want to sail. I couldnt return the tickets and couldnt sell them. I wasted $100. It would be nice if the establishment could take the tickets and give a partial return payment but no return payment is punitive. I didnt like this policy. Im sure someone wanted the tickets for the time we selected but Ill never know. Anyway, it appears to be a nice date for any couple wanting to have fun. Make sure your partner really sails cause you cant get a refund at Schooner.

We had a bachelorette party weekend and the group sunset cruise was part of our activities. We had such a wonderful time, Captain Jen and crew were honestly amazing and made the sail for us. Favorite part of our weekend, we were laughing and having a great time for the entire cruise and even wished for it to be longer!!! I would recommend this to everyone!

Sunset cruise is very nice

We booked a cruise for 24 people the morning of my wedding as a guys cruise and it was awesome. Captain Jennifer was sooo nice and knowledgable and really truly loves her job (who wouldnt). Shes been doing it for 20+ years and it shows. The boat even with 40 people had more then enough room for everyone, and the other crew members were fun too. Highly recommend it especially for group trips

A sailing experience we will never forget. The crew were wonderful, cheerful, knowledgable about the area and experienced sailors. It was a very relaxing 2 hour ride.

Have sailed on the woodwind more than 8 or so times... always a great way to spend the afternoon

Great fun. Crew is knowledgeable and engaging. Boat is comfortable, beer is cold. A wonderful 2 hours on the water.

We took a beautiful sail boat ride with the family. It was gorgeous and the kids loved it. Highly recommended.

The highlight of our vacation! Just awesome to be on the water looking at all the beautiful landscape scenery. The crew were so friendly and knowledgeable, they made you feel comfortable immediately. The beer tasting was done in a classy fun manner. I highly recommend the Woodwind and we will be doing it again our next time in Annapolis.

2 hour sails departing daily, cash bar and fun people!

We had such a great time!! The crew was very friendly and helpful. It was a great day to be on the water!

Great cruise and crew! Had the fun to go on a racing night and really enjoyed everything! Thanks to the crew and captain!

Loved it. Great boat, great crew. Would definitely do it again.

The public sailing option is fantastic! My husband and I took some family members about a month ago and had so much fun that we took some different family members this past weekend. The crew is excellent and quick to assist (one in our group this time had a mobility issue). The banter between the crew and the captain is always family appropriate and entertaining. Captain Mickey is entertaining and knowledgeable about the area. He was very happy to share the history of what you can see along the Chesapeake. The food and beverage selection is great. Im sure this will be the favorite thing we do whenever we have folks visit us!

Wow, a new sailing story! Had a good time even in the rain. The crew taught us how to be a sailor and brought us back early to avoid heavier rain. Free snack and drink

I wouldn’t bother!

We had a great time. Only wish was that it was longer.

We had a wonderful experience sailing the Chesapeake on this amazing boat! Your ticket comes with a soda, & chips but for an additional fee(small about $5-$7 bucks), you can get beer and wine. Totally worth the money, and the restaurant attached(Pussers)is great! Parking is NUTS however, directly across the street from the site at the elementary school, they do offer unlimited parking for $10.00 which is also worth it as you can stay in Annapolis all youd like without worrying about your meter running out.

Great experience on sunset sail. Highly recomend.

I have taken multiple trips on the Woodwind ships and they are a great way to see the Annapolis and nearby waterways. Staff is friendly and knowledgeable about the boat and surrounding area. They seek out passenger participation to help raise and lower sails as well as steer the ship. This is great for kinds(or adults that love sailing). A great experience for anyone who cant afford their own 60 ft sailboat!

Its a beautiful setup for a cordial date. I didnt like the no Refund policy.

Celebrated our 30th anniversary with a cruise. It was fantastic! I want to learn how to sail now! We had a great time, and will be back for a sunset cruise asap. The crew is friendly and funny, we had a great time.

Went on a cruise as part of a professional development institute. Crew was very friendly and entertaining. The event was actually a sailing race between our boat and another, but still ended up being rather relaxing. It was a beer tasting cruise as well, so drinks were on board. Great time on the whole.

Were locals and love going out on the Woodwind!

Was very compassionate and worked with my fiancé and I, in order to have a wonderful experience.

Had a great time. cheryl was especially friendly and helpful.

This was so cool. The view on the sunset sail was unbelievable. Great local craft beers reasonably priced. Crew was friendly. Highly recommend it. There were only about 10 passengers so there was a lot of room. Some music would have been a nice addition though.

Nice relaxing time we had....good selection of snacks and drinks. Friendly service.

Went sailing in late July, it was an interesting experience getting loaded up on the boats. When booking, the first vessel sold out quickly, which gave me the impression there were only 10-20 seats on board, however when boarding, there must have been 30-40 individuals on the boat, making it very difficult to maneuver and were pretty much resigned to our seat the entire time. The sail itself was fun, though I would have liked to move around to different parts of the vessel more.There was a cash bar on board which was priced reasonably, and while it did start to rain while we were sailing, ponchos were provided which we had fun with.

This was a great early evening outing. Two hour sail from Annapolis harbor. This cruise also included a gentleman doing local history and songs. I highly recommend this for anyone.

Great crew make sure you get Justin on the crew. Great guy!!! Wonderful boat. The only suggestion is they need to give out the soft drink and the snacks at the same time they do it a little backwards. And possibly get some real food on there may be some pre-made salads or excellent sandwiches other than that great

Absolutely, best way to spend the afternoon. Free snacks and beverage for first round and Captain offers a great spoken tour

Amazing place to work and take cruises with!

Schooner Woodwind Sailing Cruises was a great experience. We went with a group of Girl Scouts. We were broken into several groups and rotated around the world boat taking turns learning and completing tasks that aided in the sailing of the boat. The staff was knowledgeable and fun.

The sail was great, the overnight boat and breakfast was great, at least in concept. Berths are cramped, heads are very small, and breakfast didnt really have much of an option that didnt include shellfish (crab & asparagus quiche) for those with allergies. But those were small gripes that didnt ruin the overall experience.

Great views, great staff, great boat. Something we do yearly as a family. Kids get to help raise sails and steer the boat. Friendly staff providing drinks and stories throughout the trip. Pussers is a good place to eat and drink before the cruise. Id recommend the sunset cruise in the summer months.

Annapolis, MDFabulous experience! Boat was very nice and very clean. Crew was very professional, but fun. I feel for the ticket cost it was worth every penny. I felt very safe the entire 2 hour trip.

We had a fantastic sailing experience. It rained but they handed out plastic ponchos.The captain was very knowledgeable and professional.

Had a lot of fun aboard one of the schooners for my fiancés birthday with his family. There was live music and drinks on the water—what more could you want? Everyone was super friendly and the sunset cruise was beautiful!

Very nice staff. Sadly did not get to go on the boat because of a thunderstorm but they made refunds very easy. Hope to return for a sailboat another day.

The best cruise in Maryland!

Very fun sailing cruise around the Annapolis harbor. Highly recommend.

A lot of fun... Experienced and talking crew, learned a lot of things about sailing and the area during the cruise...

An experience of a lifetime do the complete package sail and spend the night. I love it!

Site set up is poor and unclear as to boarding policies. Got put on a superior cruise than my group without warning or any real attempt to rectify the situation. Would not try again.

We had a wonderful time sailing. The captain was great very entertaining. 10/10 would sale again

Great boat, great crew, and a great time being out on the water! Highly recommend!

Best wedding ever. Planning our special day was a snap with these guys and the wedding itself was unique and memorable.

A lovely way to spend a couple of hours on a sunny afternoon. At $44 it was quite expensive, however was worth it. The crew were incredibly friendly and if you took an interest they were more than willing to explain what was happening during the sailing.

The crew and captain were friendly and knowledgeable. I will definitely try another sailing cruise on a nice day.

Fun crew, great times! An informative and unique experience in Annapolis for tourists and locals alike.

I had a great time. The crew was great and friendly. It was great that they had drinks. Just wish they had more of a selection. Would do it again.

Excellent cruise around the bay. Crew was knowledgeable and made the trip fun.

Very fun experience but definitely would appreciate rain checks.

Had the most wonderful evening out on the Woodwind this past Thursday. I went with my boyfriend and could not have been happier with our decision to ride. The music onboard was wonderful. Brandon Hardesty of Bumpin Uglies played an amazing acoustic set that made the night so relaxing. The staff was attentive, informative, and helpful. Sage was wonderful to talk to! Will definitely be coming back. Totally worth the money for the sunset cruise.

It was great!

Fun sailing tour around the bay.

***TERRIBLE CUSTOMER SERVICE*** Really upset with our experience with these guys today. We planned a last minute trip to Annapolis and we were hoping to get on one of the boats as stand-by passengers. We went to the check in desk at 11 am to see how we could do this. We were told to show up 30 minutes prior to the time of the tour we wanted to take. As instructed, we came back at 3:30 to wait and see if there was availability for a 4 pm ride. At 4:02, we were told there were two tickets available. We paid, got on the boat and were really excited things worked out! At 4:15 right when we were about to leave the dock, two customers who had bought tickets earlier strolled in with Starbucks that they clearly just bought showing absolutely no urgency despite being 45 minutes late to the tour. After a bit of confusion, we were asked, in front of all of the other passengers, to get off the boat. My wife and I were mortified. All the other passengers were extremely displeased not only that they were leaving late, but that this company showed absolutely no respect. Their company policy seemed to not exist up to this point and the owner of the company was the one who personally had the moments of indecision then decision to boot us from the boat. They took the time of all their customers to embarrass us and lose loyalty to all but 2 very late arrivers. The situation was handled very poorly and we look forward to our Chesapeake tour on the Watermark!!!

Was a wonderful experience all the way round

Great sail on the Chesapeake bay

Really fun time. great views and drink specials

As stated in other reviews 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 advertising 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.

Makes for a pretty amazing evening to go for a sail on the Bay! Staff and Crew are very friendly and professional, will definitely go back!

Very nice ship. Crew was great.

Had a great cruise this summer!

Everything was wonderful. Beautiful at sunset.

Pleasant 2 hr sail on Chesapeake Bay.

It was fun a little pricey though

A very fun experience!

Amazing day, great crew!

Fun sail. Great crew!

Very nice sunset cruise