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Summer Staycation Series: Sailing Cruise w/ Schooner Woodwind

Enjoy a Socially Distanced Public Sailing Cruise with Schooner Woodwind

By Nicole Donnelly, MK Annapolis July 9, 2020

With the COVID-19 pandemic wreaking havoc on many families' summer vacation plans, we want to provide you with a plethora of options to make your summer the best it can be right in your own neighborhoods. Yes, maybe your flight to Florida was canceled, but we have so much to offer right here in Annapolis and Edgewater to make your summer break memorable. Stick with Macaroni Kid Annapolis each week for more Summer Staycation ideas!





Schooner Woodwind is sailing!

As you know, we've been searching Annapolis for some of the best staycation activities and experiences. After being stuck in the house for several months, we're ready to get out! When we saw Schooner Woodwind is back up and sailing, we knew how we'd spend at least one afternoon this summer.

While discussing our afternoon with our two boys, my family ended up making a list of our top "Things we Loved" about our sailing cruise on the Woodwind II. What better way to review our experience than to share that list with you? (Mom's notes are in italics underneath each list item!)

Nick, age 7
  1. I liked being on the big sailboat. It felt like we were in a cartoon or in a movie.
    (It was definitely cool. And a little fun fact for you: the Woodwind II was the sailboat driven by Christopher Walken in the movie Wedding Crashers. For more fun facts about Schooner Woodwind, click here.)
  2. I really liked it when they taught me how to tie different kinds of knots in the rope.
    (Because of social distancing, we didn't have a lot of time to explore the boat, so I appreciated that the staff brought different parts of the boat TO my family to check out and made it as interactive as they could.)
  3. It was cool when they pointed out cool things for us to look at, like the big boat that looked like the Titanic and the osprey nests.
    (I loved that the staff kept the fact that there were kids on board in mind the entire time. You could tell they were working hard to keep them engaged and entertained during the trip.)



Alex, age 5
  1. I liked that the teacher answered all of the questions I had about the boat, fish, and seaweed.
    (The "teacher" was actually a staff member, and she really did have great age-appropriate answers for all of my son's MANY questions... including "why are humans alive?" Now THAT'S a good team member.)
  2. It was fun drinking Coke on the boat.
    (When you're onboard the Woodwind, they serve complimentary soft drinks and water. They also have a variety of wines, beers, and sparking seltzers for purchase. The soda was raved about by both of my sons, who normally don't drink much of it!)
  3. One of the best parts was helping them put the sails up in the beginning. I helped sail the boat!
    (While his interpretation isn't completely accurate, my boys did get to help "guide a rope" while the sails went up and duck a few times to make room for a swinging sail.)



Husband, age "you better not put my age"
  1. It was a very relaxing trip. We had a beautiful day and the breeze and sun were absolutely perfect. It was nice spending that time with our kids with nothing to interrupt.
    (So, so true. The trip was very relaxing and we had some great conversations with our boys. Being out on the bay with the wind against your face, knowing that you're connecting with your family is a great feeling.)
  2. They took great precautions considering COVID-19. I felt comfortable being on the boat knowing we were keeping socially distant from other groups while enjoying the trip.
    (Guests on the sailboat wore masks while boarding and deboarding the boat. We also wore them until the sails were up since the staff was moving around the boat getting us going. Once the sails were up, we were cleared to take off our masks. Seats are sold by zones for each sailing and your group of 2, 4, and/or 6 are socially distanced on the boat.)
  3. The boat itself is impressive. It was in pristine condition, immaculately cleaned, and had a full bathroom and plenty of space for their zoned groups. I definitely did not feel like we were in the middle of a pandemic crisis with how natural the entire afternoon felt with their staff.
    (I love this point because it's dead on. The boat is gorgeous and knowing there is a bathroom on the ship was a great relief for us as parents... especially after the kids started drinking their sodas!)




Me! Mom!, age 25 (obviously)
  1. I love giving my kids experiences that they won't forget and this was one of them. They were able to help on the boat as restrictions allowed and they got to experience sailing which they normally wouldn't have access to.
  2. Taking kids on any type of experience like this, especially on the water, can make any parent nervous. I'm not talking about safety, though that's certainly a concern (and one that Schooner Woodwind has nailed down). I'm 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.
  3. 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 won't forget, and an afternoon of fun I think we all need. Fun, safe, educational. Does it even get better than that?

Enjoy yourself, the views, and your family's company as the Woodwind sails from the historic Annapolis waterfront, past the Naval Academy, and cruises into the Chesapeake Bay. As a family business, they take great pride in making your sailing experience a memorable one.

Click here to book your own sailing adventure with your family. Be sure to tell them Macaroni Kid sent you!


My group was provided a complimentary sailing experience for consideration for this review. All opinions are my own.