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.
Support this operator:Times are tough for the travel community right now. To show your support, consider leaving a review or posting photos of tours and experiences you have taken. Your support will go a long way in helping tour operators worldwide get back on their feet down the road

Schooner Woodwind Annapolis Sailing Cruises

Annapolis, MD, USA
About Schooner Woodwind Annapolis Sailing Cruises
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. Come Sail Away!
Closed today
Hours Today: Closed
Certificate of Excellence
Travelers talk about
Traveler rating
  • 248
  • 32
  • 8
  • 2
  • 8
Traveler type
Time of year
Selected filters
  • Filter
  • English
Popular mentions
I just completed a cruise on the Windward with Captain John and crew. I have been a sailor for over 30 years and love the water. While some “tourist” trips are a little boring with the boat motoring with one sail up. Woodward carried full sail and it was awesome to see the
Read more
We loved our sailing trip. The trip was well organized and staff were very pleasant. I would recommend it.
Read more
I found the sunset cruise a little boring. There wasn’t much to take a picture other than the schooner and the sunset, although the sunset was great on the water. You just go straight out and straight back in. The crew were all great. The enjoy their jobs and are entertaining.
Read more
I have been sailing for over thirty years and the crew of the Woodwind was fun, attentive and professional. We were with friends and we had a relaxing time catching up and enjoyed a magnificent two-hour cruise in Spa Creek & Severn River. This is great way to have a great time
Read more
Response from Jennifer K, Owner at Schooner Woodwind Annapolis Sailing Cruises
Responded Sep 16, 2019
I love this comment! I know when we started this company 26 years ago, my family and I knew we did the right business, when many people used our boat to entertain out of town guests instead of getting their boat "ready" for guests and people that didn't know how to sail. It is a bit easier. :) Thanks.
Read more
Our evening sunset cruise was wonderful. This was the first time I had been on a sailboat along with my friends. Captain Jen was very personable and her crew was top notch! We’ll be back!
Read more