Thank you,

I learned a lot last week, you were a very good instructor and helped keep us all on task.
Sure glad that I found you in my google search.

Advanced Coastal Cruising-ASA 106 with Joan, August 2023

I want to thank you again for providing this sailing opportunity on Saturday, June 10.

It was one of the best days I’ve had since the snow has melted😎

Cynthia is so skilled at what she does in both technical knowledge and teaching skills.

The other sailor (Arlene I think) was just delightful as well!



Lesson on Lake Minnetonka

Hi Captain Joan! I just wanted to say thank you for a great class! I had a great time and learned so much. Excited to keep learning and very interested in signing up for the ASA 103 & 104 in Lake Superior.


May 2023; ASA 101 on Lake Minnetonka

Hi Joan, This has been an outstanding learning opportunity and a fantastic sailing experience all around. Thank you!


Sept 2020; ASA-103/104 on Lake Superior

Hi Joan: just want to thank you for a fun and informative class. I’m really missing being on the boat with you and the other students. I can’t wait to get on my 23’ O’day and refine the skills you taught me. I will definitely sign up for another class next June.


June 2018 - Basic Keelboat

Hello Joan, A couple of things…I have been meaning to reply to you to say thanks again for the awesome class in Bayfield last month! I learned a lot from both textbooks but most from sailing and discussing the many questions a beginning great lake sailor has. I wish I could be in the ASA 106 class next week but my schedule is too crazy.


4-day ASA 103 & 104

Thank you so much Joan, it was a wealth of knowledge. I’m excited to get to my boat this weekend and practice what I have learned! It was also great getting to know you better, you made the experience awesome and I can’t wait to continue taking lessons with you!


June 2019; ASA 103 & 104 on Lake Superior

The class was really delightful, I know that I learned a great deal. Our sailing group have already been discussing the next stage lessons in the British Virgin Islands.


Basic Keelboat

Hi Joan: I’ve been meaning to write and thank you for a great sailing lesson experience. Both Matt and I were impressed by the breadth of your knowledge, diligence and teaching skills. I look forward to seeing you soon to take that gol dern test.

Lia Rivamonte

ASA 101 & ASA 103 on their 28′ Spirit in Bayfield, Wi with Joan – July 2014

Thank you so much for your kindness, patience and professionalism. I intend to continue to gain Sailing experience. I will keep your email and hope our paths cross again.



I had a great time and learned so much about the principles of docking. I am grateful that I could be taught by you. Thank you.. It was a great class and I highly recommend it to anyone.. thank you for your commitment and dedication to teaching us to be better sailors.



Thanks again for the sailing lesson. Jerry and I agree that we learned a lot, and had a lot of fun too. I am now determined to get my sailboat down to the Cities next summer.


2-Hour Private Lesson

I have to say the quality of Sail Away Sailing School (You and Claudia) has been top notch. Thank you.


ASA-101, 103, 104

Thanks for the excellent instruction. We both learned and enjoyed the time on the water. I look forward to owning my own sailboat and learning to do cruising.



The class was great. I learned a lot and Chris is a very clear, encouraging instructor. Thank you!



Chris did a great job, the weather was perfect and we had the added bonus of no speed boat noise due to the high water levels. I would be interested in finding out more information about future classes.


Sailing Discovery

Hello Joan –
I just want to reach out and express my thanks to you for a wonderful weekend of sailing, teaching and learning.  I enjoyed it tremendously.  There is sooo much to learn.  And every minute on the water helps.  And I appreciate your willingness to work with me at my ability, to answer questions, and of course to provision the boat! It was a great weekend all around.
I’ll certainly. recommend you to others interested in learning.  And I hopefully will bump into the guys at Lake Harriet sometime!

ASA 103/104 in Bayfield, WI – June 2023

Hi Joan It was a great two days of sailing in Duluth. Learned so much and can’t wait to use my new learned skills. Attached is my form for the BVI’s in 2020. I look forward to the adventure and learning.

John Watson

Basic Keelboat 2-Day course in Duluth – July 2019

Hello, Joan, I thoroughly enjoyed our 3 day check-out this week. Even though I’ve been sailing 50 years, I learned a lot that will make future cruises and charters safer and better for all aboard. You do a marvelous job at teaching the many skills needed to run a boat.


ASA 101 & 103 Test-Out, and ASA 104 on his 38′ Catalina on Lake Superior, Duluth – June 2018

Thanks Joan! I have been sailing like mad since our class on my 23 Oday when I can. I use so many of the skills I learned from the courses that I can’t even list them all! I really appreciate you and the classes I took. Take care and thanks again!


2019 Student of ASA-101, 103, 104

Joan hello. Just wanted to thank you for the class. You’re an awesome instructor and a nice person! I learned a ton. My confidence level is lifted a few notches- so merci bien!


ASA 118

It was a real pleasure to meet you and have the opportunity to learn under your tutelage. The last four days were wonderful. You really are a wonderful instructor. Thank You for everything I learned this past week. I am now looking at the 105 class. Did you say it would be “on line”? Thank You again


Aug 2020; ASA 103 & 104 - Lake Superior

Hi Joan, I just wanted to let you know that my wife and I enjoyed our sailing experience. I wrote up a little blog post about it with pictures which you can see here. Thanks for the experience!

David F

Sailing Discovery

Thanks again from Candace & me for the great sailing lessons last week….we both learned a lot and feel much more at ease with our boat on the water. I thought that you were a very good, patient, but firm teacher and appreciated your insights into our boat and how we were handling it. We wish you the best for the rest of the summer classes and for your continuing work to attract more people to sailing.

Bruce Karstadt

Private Lesson

I was sailing this weekend and I remarked on how much I have learned from you! So many things, including the preventer, jibing properly, hoisting sail, steering a course, docking, safety, all kinds of things! …thank you for making such a big difference in my enjoyment of sailing. It really has been life changing! I had the boat heeled at 20-30degrees Sunday in a decent breeze and my girlfriend said “wow, you were always nervous when it heeled this much now you are searching out the wind”! I am very grateful for the knowledge and skills you imparted on me. Thank YOU!


ASA 103 & 104

We had an awesome time with you this weekend. Ryan and I both learned a lot! I hope we get to go sailing with you again soon. You are definitely a great source of knowledge and experience that we can learn from.


ASA-103 & 104 on their 38' Beneteau

Thanks again for the amazing experience of learning to sail. Even now after we are done I almost don’t even believe it was real. I had such an amazing time and learned so much from you from techniques and terminology to tips and advice. I really appreciate all of your patience during class and making it a wonderful experience for me and the rest of our group. Thanks again for introducing me into this new world of sailing. I’m look forward to many, many years of sailing based on everything we learned in this first class. Hopefully I’ll see you at the race on the 13th and if not, happy sailing in the future!



I wanted to reach out and let you know that Becky and I had a great time out on the water with Cynthia. 
Becky and I both had a decent amount of past dinghy sailing experience, albeit many years ago, and Cynthia did a great job getting us up to speed on a Keelboat. She had a great teaching style and empowered us all to learn by doing.

Basic Keelboat with Cynthia – June 2023

Hi Joan, Me and Alecia had such a good time yesterday. Thank you so much. We look forward to taking more classes with you. 🙂 Thank you again!

Suprabha H.

Sailing Discovery 2-hour course – September 2019

Dear Joan, Thank you for a wonderful sailing class! Jane and Conrad and I all had a great sense of accomplishment as well as a lot of fun.

Dr. Heidi Jerome, New York, NY

Basic Keelboat - August 2017

Hi Joan, Thanks for being such a great teacher, sailing mentor and sailing career council. I look forward to more and greater sailing adventures.


ASA-105, Coastal Navigation - Nov 2018

Hi Joan, Thanks for a great class! It was very educational and enjoyable.


ASA 103 - St. Croix River - Nov 2018

Thanks so much for leading us in the intensive Small Boat Instructor Training course this summer. It was indeed intense, and in a good way. It was much more than I expected, with a thorough review and expansion of sailing skills communicated in a personal style that is firm and challenging while at the same time builds confidence with warm and friendly encouragement. The amount of experience you have with students of all ages was plainly evident as you reviewed with us the approaches for teaching the range of students we will encounter, from grade school kids to seniors. But most of all, I appreciate how you embody the joy of sailing. Even with the exhausting schedule, each day I began and ended the day with more eagerness to get back out on the water and try more of what we were learning. Even now as the winter weather comes in, I can’t wait for the spring and the opportunity to get out again and to pass on what I have learned, both the skills and the enthusiasm, to new sailors.

Lang Craighill

ASA 210 in Nagano, Japan, July 2015

Joan, thank you so much for your help yesterday. Your expertise and teaching are unparalleled. We both feel so much better after your instruction.

Julia McGregor

Private Lesson on a 32' Ericson

Just back from Abaco, Bahamas, where I spent 5 days on a 36 monohull with one friend. We had a super time, with warm weather, no crowds, and plenty of wind….. Mis-read some markings (actually, a couple of marks were missing) and we ran aground on a falling tide, so we got some experience with kedging off. All-in-all, an excellent trip. … So many of the things that you taught me during our “refresher course” came in handy, in particular: -Practice turning the boat under motor -Amounts of sail to use under different weather conditions -Heaving to when we needed a break from the action -Marking the anchor chain, and taking along gardening gloves to handle chain We would love to take the racing course next summer. Please keep us on your mailing list.

Bob M

3 Hour Refresher Course

As someone who started to sail later in life, I’m glad that I found the Sail Away Sailing School/Upper Minnetonka Sailing School. Captain Joan and the other certified instructors are truly expert sailors and teachers who enjoy sharing their passion for sailing with students of all ages. The sailing curriculum at the Sail Away Sailing School/Upper Minnetonka Sailing School is based on proven educational objectives of the American Sailing Association, and the instructors emphasize safety, theoretical knowledge of boat handling and sailing conditions, and most importantly, on-the-water performance, in making the sport of sailing accessible to all students. From Lake Minnetonka to the crystal blue waters of the British Virgin Islands, the Sail Away Sailing School/Upper Minnetonka Sailing School makes sailing, racing, and cruising safe and fun!

Byron S.

Cynthia was the perfect instructor for me.  She gave good direction and ensured I felt successful in everything we did over the two days.  Her encouragement was exactly what I needed to feel more confident on the water.  We had steady winds Saturday so conditions were optimal for practice.  I honestly don’t think I could have had a more perfect day.  Sunday again proved to be a day of confidence building.  The very strong winds, and gusts I have come to expect on Lake Superior, were a worthy challenge for us practicing precision sailing with mooring and MOB drills.  Cynthia showed her strength remaining calm and providing good direction when the motor died and we needed to raise the mainsail quickly.  Kudos to Cynthia!  Her inclusive discussion and decision making really helped me feel ready to get out on my own boat with way more confidence.
I could not have imagined a better experience than what I had over the weekend.

101 Basic Keelboat, June 2023

Hi Joan, I just wanted to say thank you for your help tonight. You were kind, patient, and truly helpful and I so appreciate you and your services. I would love to be connected with anyone who might want a sailing partner as you mentioned towards the end of the lesson. Thanks again!


June 2020; Private Lesson on Capri-14

Hi Joan, Thank you so much for teaching our class. It was a wonderful experience and I’m very excited to learn more.

Roger Anderson

ASA 101 with Joan – July 2018

Joan, thank you for a great experience this last weekend. I loved the way I was stretched out of my comfort zone! Have a great summer!

Tom N.

Basic Keelboat Instructor

Dear Joan, The 103/104 courses were challenging and educative. We really appreciated how you personalized the learning to make it relevant to each of your students, and adeptly administered to each of our personalities in an inclusive manner. Your sailing history and personal accounts complimented the course content and made it memorable and pertinent. Thank you for sharing your history, knowledge, and skill with us. We will confidently recommend your instruction to others.

Dr Kathleen Bailey

July 2015; ASA 103 & 104

Hi Joan, …… what a fantastic experience your sailing school was. I’m still in awe of all of us and what we accomplished. And in awe of what a fantastic teacher and skipper you are. I hope we get to do more together.

Conrad C

ASA 103 & 104

Thank you again for wonderful classes! I enjoyed them and learned so much. You are a gifted teacher!

Todd Thicksten

ASA Small Boat Instructor with Joan in Nagano, Japan – July 2013

I was just thinking about the docking class in July and wanted to tell you how much I feel I have benefited as a sailor because of it. I feel much more confident now about approaching and departing a dock. You might recall that I planned to charter “Rainbow” for the NLSC Barkers’ Island trip. On the trip, we pulled into a marina just inside the Lift Bridge and docked at a straight dock. When we left, we sprang the bow, just as you taught. Very cool!

Tony Solgard


Hi Joan, …..Patricia, Max and I are having a wonderful time learning to sail and we cannot thank you enough for your calm demeanor, thoughtfulness and expert instruction. We never realized how much fun sailing could be – we’re anxious to take the Basic Cruising ASA-103 course and very happy you’ll be our instructor. See you this Saturday. I hope we have some good wind behind our sails. Take Care, DR

Don R


I want to thank you for such an incredible experience this past weekend. I have thoroughly enjoyed starting the journey of learning how to sail. You are a phenomenal teacher and the amount of patience you have is quite remarkable.


ASA 101

What I was not prepared for was our instructor, Captain Joan Gilmore. Captain Joan is one of ASA’s best sailing instructors bar none and now I know why. Captain Joan put us through paces reminiscent of my military boot camp days. I think Captain Joan was a drill sergeant in a previous life. To say the least Captain Joan is one of the best instructors I’ve ever known. We knew about our catamaran from top to bottom and inside and out. We could handle those twin screws and snug that cat up to the dock as if we had been sailing a lifetime. I was thoroughly impressed with Joan’s teaching style and will always be grateful for instruction under her watchful eye.

Maj. Dennis Comer


The keelboat class was great. I learned a lot and feel comfortable taking out my own sailboat. Thanks so much!



Jeff’s Reviews

Thanks!!!! Had such a great time, Jeff is a great teacher. Despite only sailing these past two weekends I am definitely falling in love with the sport.



Hello Joan I attended and passed the ASA101 led by Jeff. I’d like to share that I had a fantastic experience. I am really happy and enjoyed the training. I really enjoyed Jeff’s teaching style, his patience and broad knowledge about sailing, boats and trips. He really helped me to get a few steps further on my sailing journey.



Jeff was a great instructor for 101! I really enjoyed the class with him! Thanks again!

Mark P


Hi, I just passed sailing 101 with Jeff. He was awesome and it gave me the confidence to take my boat out solo last weekend! I am interested in continuing with classes.



Joan, We had a great experience with Jeff last week.



Hi Joan, Class was great and Jeff was a great instructor!



Thanks much and thanks again for everything, it’s been a real treat going through these courses with you 🙂


ASA 101, 103, 104, 105, 106

Joan, I want to thank you for running an excellent program. Jeff is a terrific teacher. We couldn’t have been more pleased. Thanks to Jeff’s patient teaching my wife changed from hesitant to enthusiastic. We would definitely recommend your program to anyone. I think the same would be true for Steve and Barb. Thanks again for a great experience and special thanks to Jeff! We are already talking about next steps so you will likely hear from us again Best wishes for much success to both of you.



Joan, First of all, I really enjoyed 101 with Jeff. He was a great instructor and I had a lot of fun; especially Sunday with the good wind.



By the way-Jeff was an amazing instructor and the couple that was in my class was wonderful. I would highly recommend this experience.



Jeff, thank you so much for being such a kind, patient and knowledgeable teacher. The 12 hours “sailed” by and all in all it was a wonderful experience. Can’t wait to get out on the water this summer and diligently practice all those maneuvers that still need work. This class makes me want to gain far more proficiency.



We just finished up our basic keelboat class. We had a great time and Jeff was a good, friendly, helpful instructor. We actually recently bought the same exact boat that the lessons were given on so that worked out great for us! Thanks much!

Karl & Heidi


Byron’s Reviews

Thank you for the exceptional lessons you offer. Byron was a fabulous instructor. Brad, Lucy, and I learned so much from him. He’s an absolute delight to spend time with and a terrific sailor. 

ASA 101 Basic Keelboat on White Bear Lake

Thank you so much for making my solo lesson work this weekend/    I loved it!  I had such a great time and learned a ton,  Byron is a fantastic instructor and a wonderful person

I look forward to joining your 103/104 class next spring on lake superior.

ASA 101 on White Bear Lake

I had two children in the North Oaks classes with [Byron]. They had a wonderful experience and hope to repeat next summer.


Small Boat Sailing Kids Camp

Captain Ric’s Unsolicited Feedback

Captain Ric was mature, obviously very experienced as a sailor, and most important a very patient, personable, and empathetic teacher. He treated every member of our group as if we mattered and acted as though instructing us towards our success was his only concern. Captain Ric was extremely professional and made us feel ok about our lack of experience. We all thought Captain Ric was one of the best instructors any of us has had in any subject. Captain Ric took a picture of the three of us by the boat at the end of the last day and emailed us a copy, this was a nice touch. We all went from having never sailed a boat to being able to maneuver a 23 foot sail boat through the man over board drill by the end of our two day course. We all learned how to command the crew, tack, jibe, heave to, run down wind, and how to rig the boat. It was a great success and we couldn’t imagine a better fit for us. My wife and I will definitely be returning in 2021 to complete our 103-104 combo class to gain the ability to charter larger boats for ourselves. We’re glad to be sailors and can’t wait to go to the Apostles or the British Virgin Islands and rent our own boat to cruise around with.

Hey, there—What a perfect weekend for sailing! We had a great time and Captain Ric was a superb instructor. I hope our paths cross again soon,



Captain Jay’s Unsolicited Feedback

Captain Jay Lk Superior class    Sincerely thank you Captain Jay for a great weekend and foundational learning experience! Wanted to share a quick recap of some of the highlights!

Nate - ASA 103/104 in Bayfield, WI

We had a great experience with Sailing 101. Although we had prior sailing experience, we are happy to have added heaving to, man overboard, rules of the road, and basic docking to our sailing toolkit. Our instructor, Jay Biggs, was patient, knowledgeable, and humorous!



Hi Joan, I passed my class 101 class today with Jay. I’m so happy. I learned so much these last two weekends and had a great time.




 Hey Joan,  Jay was great, I learned a lot and it was a good experience. I look forward to chartering my own boat this winter with this certification.


ASA-103/104 in Bayfield, Wisconsin

Alex C’s Unsolicited Feedback

We completed our saling class with Alex today. He was a great instructor. We learned a lot and had a great time. He was patient, calm and made learning feel easy.


ASA-101 Basic Keelboat

I really enjoyed the sailing course I just completed with Alex.  He was a wonderful instructor!   He pushed us to go beyond our comfort zone but was there to guide and coach the whole way through. Thanks for the opportunity to take a class with him.  I hope it can be the first of many.

ASA 101 Basic Keelboat