Travel reviews by Trip Advisor

Trip Advisor Based on 90 traveler reviews
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Trip Advisor Friendly crew, interesting sights, fresh air, cold beer
Jan 19, 2014 by: Islandbruin from 
What more can you ask for? Only word of warning- we were in Annapolis on a weekday in July, and the parking was super-tight. Allow plenty of time to get from your car to the dock for sailing. Really enjoyed this short time on the bay.

Trip Advisor Finally did a Fall sail
Sep 29, 2013 by: Laurie_B_VA from Springfield, VA
We have been sailing on the Woodwind for 6 years now, and usually in the height of summer. Since we go more than once per year, yes, we love it. We love the serenity of being on the bay under sails--not like other harbor tours where you are on a motorized pub. The crew are always great and you can help (or not) with the sails. You never go exactly the same route because it actually does depend on the wind. Today was our first trip in Fall, and how wonderful, the boat was not full. It was very quiet and relaxed, just the right amount of chat from the Captain (Mickey) and time for a nice glass of wine. And, aha, with today's sail we are in line for our fourth free trip and shirt!

Trip Advisor Love this sunset cruise!
Sep 21, 2013 by: momheis from Millersburg, Pennsylvania
Every year we travel to Annapolis and take the schooner woodwind sunset cruise. The staff and captains are great. They ask for help to put the sails up and even let you take a turn sailing the boat. Drinks are served on the boat. We make this trip every year. After 5 sailings, you get a free sail. Check it out!

Trip Advisor Wonderful, relaxing experience
Sep 14, 2013 by: DogWorld from VA
The schooner is fast, sleek and clean. The crew is attentive and fun. It was fun to help raise the sails and steer the boat. The bay is beautiful and the two hour cruise is perfect. Definitely recommend it.

Trip Advisor What could be better than sailing in Chesapeake Bay?!
Sep 12, 2013 by: BirdieBaker from Vancouver, Washington
If you want to have a truly remarkable experience when visiting Annapolis, take a 2 hour sail on this beautiful boat! Our skipper, Mike, was interesting and fun as was his crew. You can help hoist the sails and steer the boat if you'd like. Annapolis is beautiful from the water, and the thrill of racing through the water on this spectacular schooner will not disappoint! You'll be shopping for sailboats next!

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