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Creating Confident Sailors with Easygoing Personalized Training

Reviews from Yelp and around the Web:

Hello Island Dreamer

Just finished your courses 102-114 for myself and my wife participating but not trying be be licensed. It turned out to be a great experience for both of us. I accomplished some goals and we both had a great time.

Captain Derek and his understudy Jim LOL were great teachers and very easy to be in close quarters with for that length of time.

While captain Derek was teaching Jim was whipping up many taste sensations that would sweep the nation.

Traveled lots but this was truly a memorable vacation.

Highly recommend and great for couples!!

Randy and Yvet

“Best Biscayne Bay Sail!”

5 of 5 bubbles

We couldn't have asked for a better way to end our trip to South Florida. Jamey was an excellent guide, teaching us more about the Bay of Biscayne and sailing than we ever expected and also recommending a fabulous local joint to get dinner at (Rod Benders!) It was such a treat to be on the water, snorkel and paddle board through the mangroves of Adams' Key (even saw an adorable sea turtle!), and enjoy such a unique and lovely National Park.

Visited November 2016


“Captains Derrek and Stephanie are AWESOME!”

5 of 5 stars Reviewed 2 weeks ago

Don't let their ages fool you, they are two of the best ASA Instructors out there! We took the 101 and 103 class and are going to meet them at Grace Harbor Watersports, LLC in Oriental, NC this summer for 104. So, either FL or NC, look these guys up if you want to learn to sail! You will feel very confident sailing after living with them for 6 days on a well equipped sailboat! They are firm about testing and make sure you know the materials, politely reminding you if you aren't getting it. The food is great and they work hard to keep you from hunger pains during the day. While the classes are almost constant there is plenty of time for play swimming or kayaking and one night on shore. Not too many naps! They charter trips in Greece and one is coming up this Sept...I am sure that will be a good time! Thanks so much for a "non yelling" sailing class and thanks for not flunking me when I yelled at Mark a few times! I was politely scolded! Great time, worth every dime!


My husband and I just spent a week sailing with Capt Harold and Capt Margie. We had a terrific week earning sailing certifications and had a blast! I can't say enough great things about their level of experience and their hospitality. Would highly recommend them!


“Relaxing day of sailing in Biscayne National Park”

5 of 5 stars Reviewed 2 days ago

The sailing trip with Island Dreamer Sailing was an outstanding way to experience Biscayne National Park. The online booking was easy. We were contacted by the captain, Hans, ~5 days in advance of our trip to see if we could reschedule because the day we had chosen was going to be extremely windy and the trip would most likely be cancelled that day. We really appreciated this forward thinking, and he was able to reschedule our trip for a better day. Hans has a beautiful and well maintained sailboat, and we were very comfortable while aboard. We sailed to one of the outer islands, Boca Chita. During the trip Hans told us about the history and nature of the area and he was very enjoyable to talk to. When we got to the island, 2 people in our group took out the kayak and one attempted to SUP. We paddled around the neighboring island and then enjoyed a picnic lunch on Boca Chita. Unless you have your own boat, I don't know how else you could truly experience this park. All in all, we had a fantastic day.

Visited January 2016

“On Yelp today;

5.0 star rating 12/24/2015

Awesome day sailing trip in Biscayne National Park. The staff was terrific teaching sailing to everyone on board who wanted to learn, including our teenage boys, very patient. Knowledgable about the area, and created a friendly atmosphere on the boat. Great time snorkeling and paddle boarding.

Great day sail”

5 of 5 starsReviewed 5 days ago NEW

We had a great day sail in Biscayne National Park. Harold and Margie are natural teachers. They were very patient with ours teenage boys and anyone on board who wanted to learn about sailing. Friendly atmosphere and great time snokeling.

Visited December 2015

Helpful? Thank Laura K


Ask Laura K about Island Dreamer Sailing

This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

Harold, I just wanted you to know that Carolyn and I had an exceptionally good time being educated by Stephanie and Derrek. Everything went perfect! Stephanie and Derrek were not only great teachers, but we enjoyed their company as well.  

It looks like Carolyn may be available in January for the next steps in our journey – 104 & 114. As our schedules firm up, we will contact you. If Stephanie and Derrek are available then, we would want them to continue being our teachers.

Harold: just a quick note from some former students, Michael L and Rebecca K. We did our final two bareboat cert. courses through Island Dreamer back in 2011/12. Crazy Chuck Koucky was our captain. Anyway, not six months after we got our certifications we chartered a 37ft. Hanse in the Dodecanese Islands of Greece and sailed for 2 weeks between Kos and Patmos. We took a captain for 4 days, it being our first charter, and we were glad we did. Right out of Kos Harbor the winds were blowing 30 knots and the seas were 7 to 8ft.. Nothing we ever encountered in blissful Biscayne Bay. Anyway, it was a huge learning experience, along with figuring out Mediterranean docking, something we became quite proficient at. We followed that charter with a 2 week charter in the Grenadines, sailing from St. Vincent to Grenada and back. again, we took a captain for several days and, again, were glad we did, as we quickly learned how to reduce sail when a squall hits, and I mean “reduce” sail at your peril. So now, we are headed back to greece to sail a 39 Oceanis for 2 weeks in the Cyclades. It’s been a great experience and each one has taught us a tremendous amount about sailing. Anyway, just wanted to let you know you’ve given birth to a couple of Boat Heads. Say hi to Chuck for us and tell him our sailing lessons have been put to good use and we’ll never forget that night at Cape Sable. Take care, Michael L, Coconut Grove.

Good morning Harold and Margie.  I just wanted to drop a little note to tell you that Sharon and I are finally going for it.  We will be moving aboard our new home - "Temptress", a 1984 Moorings Morgan 50 - in our beloved Virgin Islands this January.  As you might remember, we were heavily contemplating our current "life" and what it's all about when we sailed with you.  2014 turned out to be brutal for loss of friends and family to cancer far before their time.  This combined with an opportunity that seemingly came out of nowhere was the push it took for us to make the move.  It's time to stop letting life pass us by and to start living it.

We are excited and terrified all at the same time.  Selling our possessions and preparing for the move is an emotional and scary transition, full of uncertainty.  One thing is certain though, I feel we chose the right school with you and I have no regrets for that.  You made Sharon believe we could do this and made her comfortable throughout our ASA coursework.

When we departed Island Dreamer, we wrote in a thank you card that one day we hoped to send you a picture taken from the bow of our boat in the Caribbean.  I'm excited to say that day is soon coming.  We launch Temptress this November and our final move comes in the first week of January.  2015 will be the first chapter of our new life.

Tim And Sharon W.


Terrific husband-&-wife co-captains, Harold & Margie(also a great chef) Ochstein, Hoosiers who moved to FL! Took us on a hike to the top of a volcano, ate at taverna along the way. The 6 of us clicked right away(same age) -- Harold kept buying sweets/had radar for bakeries & chocolate shops. Drank Mythos & Fix beer with Margie, who shared recipes & sailing tips. Pat and Maribel P.


Good day Harold,

 Donna and I are now back home in Pennsylvania from our week long sailing adventure with Stephanie and Derrek.  We can’t believe it’s over already.  We want you to know we had a fantastic time and learned so much from Stephanie and Derrek.  They have a huge skill set not only with sailing, but with teaching, mentoring, advising and making us feel welcome and comfortable.  Their level of experience, maturity and professionalism is greatly appreciated.

 Our week was filled with learning, getting our confidence level up and working on the necessary skills for our certification goals.  We appreciate all that Stephanie and Derrek have done for us and I’m especially grateful in how they were able to keep us at ease (relatively speaking) and elevate our skills allowing us to confidently demonstrate what was learned.  I could see Donna’s progression to the point of her showing command of managing the vessel.

 We highly recommend Stephanie and Derrek as ASA instructors and have absolutely no hesitation in utilizing their services in the future.  You have two winners in Stephanie and Derrek.  If they were part of my staff I, personally, would do what it takes to keep them.  This trip and learning experience truly exceeded our expectations.

 Thank you for offering a concept that works for couples.  It did for us.  We hope to continue our relationship with Island-Dreamer for further ASA certifications as well as future charters.  Please feel free to use any/all of this review on your website and advertising materials.  We hope to see you again in Annapolis this year.


 Paul and Donna W.

2/21/14 Stephanie & Derrek,

 Linda, Michael and I would like to thank you for the great sailing week we had sailing with you.

 The ASA instruction for Michaels ASA 103 & 104 certification was the top of the line, very good job. The boat was excellent for training, the shallow keel allowed us to go into some anchorages we otherwise would not have seen, just an all-around great experience for us all.

 Stephanie and Derrek you  are both excellent sailors and teachers, and the food was great also.

 We hope to sail with you again in the future, keep up the  good work.

Paul, Linda & Michael  

2/19/2014 Russell and I just wanted to send a note to say what a wonderful weekend we had sailing with Derek and Stephanie.  We really learned a lot and they were great teachers.

Thanks.  And thanks to a great anniversary weekend learning how to sail.

Julie and Russell

 1/28/2014 Hi Harold,  I had a great time sailing with Stephanie and Derek this weekend! They are incredible captains and instructors, I really learned a lot on this trip. The boat surpassed my expectations and all of the food/hospitality was fantastic and much appreciated.   Thank you for squeezing me in last minute and making everything work. Another big thanks to Derek and Stephanie for all of their hard work in helping me become a stronger and more confident sailor. You have a great team and I hope to return sometime for 104.  Thanks again, Jayne

9/23/2013 Captains Harold & Margie made our trip to Greece a wonderful, relaxing and informative trip. Sailing, snorkeling and dining in the Northern Cyclades Islands was a dream come true.

The local people were welcoming and  and full of smiles.

We felt at home on the boat as well as on the islands.

We also enjoyed getting to know our sailing companions from Texas.

Thanks a million Harold & Margie!

Happy sailing,

Tom & Cynthia Atha

Granville, Ohio

2/3/2013 Captain derrek and Captain Stephanie were great teachers and hosts on the Morning Dance!  We booked a 7 day trip to complete 3 levels of ASA certification. My husband and i were excited to do this together with another couple. We easily passed our tests thanks to our great captains who made sure we were fully prepared. Captains also made sure we had lots of time to learn and practice sailing techniques.  Lots of firsts for me since I had never even driven a power boat before!  We really enjoyed our trip and time with derrek and Stephanie.  They also prepared great meals and we were able to go to shore for a few meals as well!!!  Very memorable trip!!! Tammy H

 1/2/2013 My trip with Island Dreamer Sailing School was amazing, they did an excellent job of the instruction, food, etc.  I would recommend them strongly for captained charters and courses.  I sailed with Derrek and Stephanie for five days on the Morning Dance and successfully achieved the ASA 101 and ASA 103 courses.  Derrek and Stephanie are excellent instructors, my confidence level aboard a sail boat has increased greatly.  I look forward to booking another trip next year for the ASA bareboat and navigation certifications with Island Dreamer Sailing School.  I trained on the 20' Kermit sailboat for a day and it was very valuable; I highly recommend it for new sailors! The Morning Dance was a great boat to spend a 5 days on; the maintenance on the Morning Dance is good.  Kevin J

10/24/2012 We have sailed with Captains Harold and Margie three times.  They gave us the confince to buy a boat and we have crossed the Gulf Stream four times now.   You will not get a more knowledgeable team.   Looking forward to  sailing with them again. From Admiral Shirley and Captain Bob M


My girlfriend and I were visiting friends in Ft. Lauderdale and we decided to try to find an ASA-certified school that could give us intro lessons on short notice.  Luckily, we found Captain Harold and he bent over backwards to accommodate us and went on to give us great hands-on lessons and a very detailed treatment of the ideas and rules that govern sailing.  He was very kind and friendly throughout, and is very clearly an expert at what he does.  I would strongly recommend him to anyone interested in learning how to sail or building on their existing knowledge.  Thanks Capt. Harold!!  Tom G


We just returned from our four day couples sailing course and it was a wonderful (and unique) experience. Our goal was to achieve the ASA 101 and 103 certifications, and with Harold and Margie's help we did it with time to spare. Both of the Ochsteins are skilled sailors, patient teachers, and have an encyclopedic knowledge of the local waters in the Keys and the Miami area. We got plenty of sailing time in the big 41' Island Dreamer  and also in their smaller (and less intimidating) 21' boat, and still had time for a couple of fun evenings on shore. A bonus was the chance to see some of the local flora and fauna up close and personal - a big sea turtle, half a dozen porpoises, and and endless variety of birds native to the Keys. The calm, broad, shallow waters of the Keys turned out to be ideal for a couple of newbies with no sailing experience. What really makes this different from the average sailing school is that Harold and Margie aren't just good instructors; the Island Dreamer is also their year-round home (they live aboard), and we got to know these lovely and hospitable people very well by the end of our trip. If your taste in vacations runs to the intimate bed & breakfast experience, and you want to become a confident sailor, you'll love the Island Dreamer experience. If you're more the Marriott type, or think that twelve meals a day on a huge cruise ship is the perfect holiday, then you may want to think again; Island Dreamer (and sailing in general) may not be for you. It was perfect for us.  Wes N


The Very Best!!!!!!!!  Harold and Marge are the friends you have always known but you just haven't met yet.  The sailing and navigation training is the best you can recieve.  The experiance, well I was lucky enough to learn more about myself.  If you don't go sail with them you are missing one of life's special moments.  David & Deanne B 2010

Comments From Our Mailbox:

Harold and Margie- Thank you so much for a great week and helping us set our plans in motion. We have a long way to go but the skills and confidence you helped us gain this week are invaluable. We had a great time aboard Island Dreamer with you and enjoyed the night life as well. We hope to see you out on the water again soon. Tim and Sharon P.S. With any luck hopefully I can email you a picture from the bow of our boat in the Caribbean.

Hello Harold, Louise,

Thanks again for this 4-day ASA106 class in the Keys. Beside the fantastic weather we were lucky to have, the class was terrific and we truly learned more in that class than in any other previous practice classes.

Great accomplishment and great milestone in our sailing education.

Thanks again and looking forward to future sailing adventures with both of you.


Jean-Dominique T.


Harold & Margie,

Sorry for not writing sooner but since we arrived home from out trip with you (May 2010) our lives have been at full speed.  We cannot thank you enough for the hospitality and education you both provided during our ASA 103 & 104 classes.  

It was a great educational vacation.  From the moment we stepped on board the Island Dreamer, you and Margie made us feel at home.  Chris especially enjoyed Margie’s cooking.  Each morning started with a good breakfast and then right into the hands on education, which was the purpose of our trip.

Not only did we increase our skill level daily, but you made time for us to enjoy the sites, snorkel and even listen to some island music at the Tiki bars.  We loved stopping at the different Keys along our journey.

Once home, we went right into sailing season and we felt more confidence with our skills.  I raced against Chris last month.  We crewed for different captains on Hobie Tigers.  We had loads of fun, but I came in second.   I don’t mind, it was a learning experience and I hope to beat him next season.

Chris finished the spinnaker for our Hobie 16 and I am attaching a picture.  We also have video coming.

Thank you both for a wonderful vacation and an education we will use for a lifetime.

Best regards,

Kathleen & Chris G.

Virginia Beach, VA.

See you at the Sail Boat Show!

Hello Captain Harold,

First of all I wanted to once more thank you VERY much for such a great experience and sailing course.

My wife and I are very happy and pleased with the course and the entire experience.

Thank you once more to you and your wife for a very professional as well as personal experience.

Sincerely yours,


Greetings Captains Margie and Harold,

We had a fantastic week sailing with you on Island Dreamer in the Florida Key. The lessons, your excellent instructions and sailing knowledge are exceptional. After returning to sail our boat it was surprising how much our sailing skills had improved. The week of instruction, food, company, laughter and stops along the way truly exceeded our expectations.

Have a great Thanksgiving and Happy Sailing,

Monica and Keith

I don't believe we could have asked for better captains. What a terrific partnership and your knowledge and patience with the boys (and the parents!) was truly appreciated.  The memories you left us will be

forever cherished.  Thank you, thank you, thank you, thank you!

Robin N.

Thank you for the best sailing week.  Your patience and knowledge was very appreciated.  I have learned so many new things this week and loved listening to both of your lifestyles and experiences.  You are living what most people can only dream about.  You were both so kind to us - you

are truly amazing!  I am so thankful for this experience and feel so blessed to have had you both for our captains. We could not have asked for a better trip!!!  Thank you!!!

Mary P.

Your ability to educate and teach is incredible.  Thank you for a lifelong memory . . .Again, thank you for the great adventure last week.  We all had a great time and spent the entire return flight talking about our adventure.  It really was an experience we will never forget.

David C.

Kansas City, Kansas

What a great week sailing with you and the Boy Scouts. It was a most excellent trip.  It will always be a wonderful memory for James and I.

Bill B.

Once again, thanks so much for being such a large part of the crews successful trip.  They boys are still talking about it and I’m sure it will go on for quite some time.

Cal C.

West Point, NY

Thank you for the most awesome week!!!  Your patience was beyond our greatest expectations!  Thank you again.

Colleen B.

Thanks for a wonderful time!  This was one of the best scout trips I have ever been on.

L. A.

Thank you for a wonderful time.  You are a great team and were wonderful with the boys.

Mark N.

Thank you for a wonderful week of sailing.  Life aboard was a new world for most of this land-lubber crew.  Your expertise and skill were beyond expectations.  Your ability and patience to teach and work with the boys made the experience truly a life shaping experience.  Many thanks for an awesome week at sea.  

Phil R.

Westminster, CO

Thank you for making our trip a terrific experience.  The young men that were privileged to spend this week with the two of you will reflect upon this trip with great fondness.  In addition to all the fun they had, they also learned a tremendous amount from the both of you.  


The roses, thorns and rosebud talks were great!  We enjoyed the great education on sailing, deep-sea fishing, and snorkeling the best areas around.  Thank you for your great gifts, talents, and abilities that you have shared with us.  It was a great blessing to all of us!

Dr. Rick G.


What an inspiration for our boys--the snorkeling was great and the company was wonderful.  Thanks so much for the memories!

Dan T.

Your gift of teaching and providing a positive example . . . was a blessing.  Thank you both for the enlightening experience.  We with you the best in life and happiness.

David C.


Great fishing, great diving, awesome sailing.  A fantastic learning experience.  Captain created a great atmosphere for our group.

Warren S.

Colorado Springs, CO

We had a great week.  We learned a lot, saw a lot.  It was just a great experience.  Thanks!


I wanted to thank you for the good week that we had sailing, fishing and snorkeling with you. My son Kevin is still talking about the trip. He said that he felt right at home on the boat. The motion had no impact on him. Your temperament is well suited for working with the boys. I'm not sure that my patience would hold up as well as yours did.

Greg S

ASA 101,103,104 combo class sunset at the dock