Google users rate Annapolis Sailing Adventures, LLC five out of five stars based on fifty-three reviews, with the owner responding to seventy-four percent of them. Customers consistently praise the knowledgeable and accommodating crew, who provide educational sailing lessons and handle weather-related rescheduling effectively. The vessel is described as spacious and well-maintained, suitable for groups and families, while the service includes helpful communication and a comfortable atmosphere for private charters.
Data from Google, last updated October 25, 2026.
Reviews from Google, shown as published (original wording, unedited).
Amazing sailing trip with Rick and his first mate Matt. Very experienced and knowledgeable and learned a lot while enjoying the beautiful waters! Highly recommended if you are looking for a sailing trip in Annapolis!
Thanks Elaine - great sailing with you all!
Captain Rick gave us an exceptional boat tour of the Chesapeake bay! Highly recommend, no better boat tour in Annapolis!
Thanks Chris - hope you join us again!
My wife and I had a great experience sailing with Rick and Annette. I would highly recommend them. They’re both very knowledgeable and accommodating. Thanks for making our anniversary special!!
Thanks Shane - hope to see you both again!
We had a great trip with Rick and Annette. I would go again!
Thanks - hope you sail with us again after the big day!
We had such a wonderful experience with this sailing company for our engagement photos! Rick was incredibly responsive throughout the entire planning process and was especially helpful when we needed to come up with a rain plan. He made everything so easy and stress-free. The sail itself was absolutely beautiful, and our engagement photos turned out perfect! It was such a fun and unique way to capture this special time for us, and we couldn’t be happier with how everything turned out. We highly recommend them for anyone looking for a beautiful and memorable experience on the water!
We had the most incredible day with Annapolis Sailing Adventures! Our family of six (including an 11-year-old and a 9-year-old) booked a sailing and motorboat adventure, and it completely exceeded our expectations. Rick and Annette are beyond experts in their craft, but what truly made the experience unforgettable was how wonderful they were with the kids. They spent so much time teaching them the ropes, explaining how everything worked, and showing absolute patience the entire time. They made the kids feel like an important part of the crew. We couldn't have asked for a better day on the water. The ultimate compliment came from my 9-year-old nephew, who announced at the end of the day, "Now I want to learn how to sail like Captain Rick!" If you are looking for a first-class, family-friendly boating experience in Annapolis, look no further. Thank you, Rick and Annette, for the amazing memories! We will definitely be back.
Thanks Nicole - hope you all join us again! Austin will make a fine sailor…
We had a fantastic day on the Bay with Rick and Matt! They were knowledgeable and personable and the boat is beautiful. Recommend without hesitation.
Joanie - enjoyed meeting you all - hope to see you again!
Our group of six had an amazing sailing charter with Rick and Annette! From the moment we stepped aboard, they made everyone feel welcome, comfortable, and at ease. The boat provided plenty of space for our group to relax and enjoy the experience together while taking in the beautiful scenery and peaceful atmosphere. Rick and Annette's knowledge of sailing was impressive, and they shared their expertise throughout the trip. We learned so much about sailing, navigation, and life on the water. One of the highlights for our group was the opportunity to be hands-on. We got to help raise the spinnaker and even take turns sailing the boat, which made the experience both exciting and educational. Whether you're sailing with family, friends, or a larger group like ours, we highly recommend a charter with Rick and Annette. It was the perfect combination of relaxation, learning, and fun. We left with great memories and a deeper appreciation for sailing.
Thanks Kimberly. Enjoyed meeting you all. Visit again sometime. Rick
Rick and Annette are lovely, experienced, and gave me and my family a great sail.
Thanks Jennifer. Hope you all sail with us again. Rick
Fantastic day on the Bay. Rick and Annette are 5 star hosts
Thanks Ken - hope you all join us again soon.