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“A beautiful sunset sail”
Review of Schooner Woodwind

Schooner Woodwind
Ranked #5 of 32 Tours in Annapolis
Certificate of Excellence
More attraction details
Attraction details
Recommended length of visit: 2-3 hours
Owner description: The classic, wooden 74' Schooner Woodwind sails multiple cruises daily (in season) for public and private charters. Up to 48 passengers on each of our twin schooners. Whether a couple, family, party or corporate, we can accommodate you. We also have a Boat & Breakfast available (in season) on Saturdays. Come Sail Away!
Reviewed 30 August 2017

We went for my husband's birthday last Wednesday for a sailing race but due to no winds it was cancelled. However we had such a blast sailing into the sunset, it was just gorgeous. A perfect ride for a special occasion or if you are just visiting the city. Highly recommend it.

Thank MyTicklefeet
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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"sunset cruise"
in 36 reviews
"captain and crew"
in 28 reviews
"beer and wine"
in 10 reviews
"wedding crashers"
in 7 reviews
"bay bridge"
in 22 reviews
"bag of chips"
in 4 reviews
"wednesday evening"
in 5 reviews
"amazing ride"
in 3 reviews
"relaxing afternoon"
in 4 reviews
"two hours"
in 15 reviews
"great sailing"
in 6 reviews
"perfect weather"
in 4 reviews
"sailing experience"
in 5 reviews
"hour trip"
in 5 reviews
"lots of fun"
in 4 reviews
"naval academy"
in 15 reviews
"visiting annapolis"
in 5 reviews
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35 - 39 of 273 reviews

Reviewed 29 August 2017 via mobile

My wife and I did the boat and breakfast. When I called to make the reservation I was told exactly what to expect.
The sunset Cruise was beautiful. The crew was extremely helpful and attentive. They noticed I had an empty drink in my hand, they came by to throw it out, so I could enjoy the trip without having to throw it out myself. There was no pressure to purchase more drinks.
They pointed out all of the sites
Captain Jen was great. Breakfast was fantastic.
Sleeping on a sailing ship is not for everyone, but if you ever wish to do it, I would highly recommend the Schooner Woodwind.

Thank MillerOD
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 27 August 2017

We had not been on the Woodwind in years, but bought tickets for a two-hour afternoon cruise on a glorious late August Saturday afternoon and we were not disappointed.

Brilliant sunshine and a brisk wind allowed us to sail most of the way across the Bay and back, to get up close and personal with all kinds of boats and ships on the Bay, to have a hand at hoisting sails and steering the boat and to interact with Jen, the very lively and personable owner.

Soft drinks (one included) as well as beer and wine are served on board, as are snacks. There are bathrooms ("heads") but you would be well advised to start the journey with your bladder on empty. Jen's autobiographical story of coming into the boat ownership and sail-for-hire business is most interesting and she tells it comically yet humbly. (Recommend you sit near the wheel to hear it).

Even though we are fairly local to Annapolis and have good knowledge of attractions, the Woodwind is something we would do again and again.

Thank 61Boss
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 24 August 2017

We did a Saturday afternoon sail and had perfect weather and wind conditions. We were on the Woodwind 2 with the all female crew, and they gave us quite a good sail.

The ship is well maintained and the crew is all well trained and professional while having a good time.

On our sail we made it almost all the way to the bay bridge but had to turn around just shy due to timing.

The trip was also great for the kids on board as well as some others who got to help raise the sails and also pilot the boat during the trip.

I would highly recommend taking a sail with this crew!

Thank gd1147
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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Reviewed 18 August 2017 via mobile

Although there wasn't much wind at all on the day we went out for the 11am sail, seeing the bay by sailboat was a treat. Much quieter and more relaxing than a motorboat tour, and the crew took great care of us with snacks and drinks. Two hours was a perfect duration cruise for our family group, and the Woodwind was conveniently located and well-priced.

Thank Kim D
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC

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