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“great way to experience sailing and the Chesapeake Bay”
Review of Schooner Woodwind

Schooner Woodwind
Ranked #5 of 31 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 10 October 2017

This was a great trip. I was thrilled that we were able to book so short notice. I called and left a voicemail around 9am. They called me back at 10am and were able to fit us in that afternoon (and during the sailboat show which is a crazy busy weekend.) I almost didn't call; it seemed like such a longshot. And I'm so glad we did it. This schooner is an amazing sailboat. We had good winds and we could really see how fast this boat could move. Our captain was amazing. She could maneuver this huge boat through a crowded harbor so effortlessly. I was very impressed. I am not an avid sailor, have sailed a few times in the Caribbean. This was my first time on the Chesapeake Bay. I can't wait to do it again. Oh and the price was very reasonable. $35/person for 1 and 1/2 hours of sailing.

BTW, I see a couple reviews from others complaining they couldn't get a refund or change their reservation to a different day or time. I have to say, there aren't too many activities/events that would allow you to do that. And in our case, when I made the reservation, they were very clear about the policy.

1  Thank mquest
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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28 - 32 of 273 reviews

Reviewed 26 September 2017 via mobile

I am a seasoned boater and this was a first for myself and fiancé. What a wonderfully relaxing afternoon. We did the 3 pm tour and there was about 10 of us and crew was personable and knowledgeable. I got to steer the boat and for quite awhile. We bought our tickets 15 minutes before sail but end of season and a Monday. Highly recommend Monday or Tuesday their slow days.
Can't wait to do it again and bring my family! Thanks again for making memories with us!

Thank lisabN5049RG
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 18 September 2017

My husband and I booked a "specialty cruise" for Sunday, September 17. It was a participatory sporting for the sail boat, AND 21 other classic wooden boats.

This regatta is an annual event in Annapolis, and we were fortunate that the weather [mostly] cooperated. The course consisted of 3 laps around a present course on the Severn River. Our cruise lasted about 3.5 hours, so it was both longer, and more expensive than many of the other Woodwind cruise offerings.

Lunch, soft drinks, and bottled water were included in the price. We were pleasantly surprised by the quality of the bagged lunch, choice of sandwiches, vegetarian option, and sides as well as dessert.

The crew was pleasant and efficient, as again, they were racing the other schooner, Woodwind II. It was a unique sailing experience, to see the crew in action, competing in the regatta. Additionally, the were info sheets about many of the other participating boats, which added to the fun.

Our captain, Jen, was engaging, and pointed out some of the landmarks on the coast, explained the course, and made periodic announcements about the progress we and the other boats were making.

Young children aboard our boat were invited to steer the boat, as well as to assist in taking down the sales as we headed back to our bert. Overall, can't say enough about this great experience!

Thank Deborah C
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 17 September 2017

This company refused to offer us a refund or even a different sail time when our son was sick and would be unable to sail the day we bought the tickets for. Only when we went to our bank to contest the charge did they offer us a "standby sail" which meant we would have to wait by the boat to see if 4 people didn't show up for the cruise and then we could board. Totally unreasonable...and VERY unfriendly customer service. I would not recommend anyone with a family choosing this sailing service.

I can't comment on the actual sail because we were never able to actually go on one even though we paid them $160.

2  Thank ford4040
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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Reviewed 10 September 2017 via mobile

For nearly 20 years the Schooner Woodwind has been, literally, my happy place. Typically it's my husband and me, celebrating an anniversary and it's always amazing. But sometimes we bring small children or teenagers or out of town guests and it's still amazing. The crew always goes out of their way to make sure your experience is the best it can be. Today the sail was a bit cool and my teens were chilly and suddenly - blankets were produced! I swear they anticipate everything. Do yourself a favor - book a cruise asap

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

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