We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

“Great sailing boat, even better classic wooden boat regatta!”
Review of Schooner Woodwind

Schooner Woodwind
Ranked #3 of 31 Tours in Annapolis
Certificate of Excellence
More attraction details
Attraction details
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 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
Write a ReviewReviews (254)
Traveller rating
Traveller type
Time of year
All reviews
"sunset cruise"
in 32 reviews
"captain and crew"
in 26 reviews
"hour sail"
in 14 reviews
"beer and wine"
in 9 reviews
"chesapeake bay"
in 24 reviews
"wedding crashers"
in 7 reviews
"bag of chips"
in 4 reviews
"amazing ride"
in 3 reviews
"two hours"
in 15 reviews
"wednesday night"
in 7 reviews
"relaxing afternoon"
in 4 reviews
"great sailing"
in 6 reviews
"perfect weather"
in 4 reviews
"sailing experience"
in 5 reviews
"lots of fun"
in 4 reviews
"visiting annapolis"
in 5 reviews
"severn river"
in 6 reviews

11 - 15 of 254 reviews

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
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
Reviewed 3 September 2017

We took our family on the Sunset Sail a few weeks ago. It was lots of fun. The crew was very friendly and the sunset was amazing.

Thank lparker220
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
See more reviews
Reviewed 3 September 2017

I made the mistake of buying tickets six days in advance. 3 days before the trip, the weather report went from great to horrible. Hurricane Harvey was coming up this way and was going to dump a bunch of rain. I called them and explained that I'd be traveling with 6, 7, 83 and 85 year olds and had reservations about putting them on a boat in the pouring rain. I was bluntly told no changes allowed even due to weather. They had plenty of spaces available over the next few days. The day of the trip, I called 3 hours before departure time to get the status of the trip and was told that they just had a cruise come back and everyone had a great time sailing in the rain. Once again, no effort was made to accommodate my concerns or allow any changes. Once you buy a ticket, you either get on board for that trip or you're out of the money you spent. Yes, it was my fault for not paying close enough attention to the language on the ticket purchase page which says no changes, but this truly is a company that has no concern for its customers. According to the Weather Channel, it rained the entire time the trip was to take place. I don't regret making a responsible decision to keep my entire family out of that mess and I certainly won't regret sending this company any more money.

1  Thank stevear98
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Bill M, Manager at Schooner Woodwind, responded to this reviewResponded 6 September 2017

Thank you for taking the time to provide your feedback, we hope that many future customers take the time to read your review as well as this response. You are absolutely correct that we do uphold our policy of sailing rain or shine unless the captain deems the conditions unsafe to sail. We are very upfront about this policy and it is the first policy listed on our "Buy Tickets" page directly to the right of the rain cloud graphic on the page. No refunds or exchanges is the next policy listed on the page. These policies are reiterated in our Contract of Carriage as well as on the receipt/itinerary that is sent via email following purchase. This is no different than when you purchase tickets for an outdoor concert or ball game.

On Saturday, 9/2/17 the Annapolis area received remnants of Harvey. It did rain most of the day, but there was never a question of safety to passengers or the boats themselves. The wind was coming from the right direction allowing the Woodwind to sail past the most photographed and painted lighthouse on the Bay, Thomas Point Light. Which we only get to about 10% of the time due to conditions. We ran 5 trips that day and received positive feedback from guests throughout the day.

We are very sorry that you chose to not make the trip and enjoy this sailing experience like so many others. We also hope that future guests will read this review/response and think about any special needs or limitations before purchasing advance tickets. While we always suggest purchasing tickets as far in advance as allowed in order to prevent the disappointment of a sold out cruise, there are circumstances where waiting for weather reports to improve before purchasing tickets is the better course of action.

Thank you again for your feedback, we hope to be able to welcome you aboard sometime in the future.

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC

Been to Schooner Woodwind? Share your experiences!

Write a Review Add Photos & Videos

Owners: What's your side of the story?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing