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Captain Margie and Captain Harold have been married for 32 years and Live Aboard their sailboat in the Florida Keys. They blog about their sailing adventures and the sailing and cruising lifestyle.
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Harold Ochstein
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Island Dreamer Sailing Exploring a Couples Life Aboard a Sailboat

English - Sailing, Cruising, Sailing School
Http://SailingTheIslands.com
Island Dreamer Sailing · 3M ago

Sail In Greece With Us This September

Margie and I have just made arrangements to charter a 50′ yacht with room for 3 couples to explore the Greek Isles surrounding Athens this September. We can’t wait! Join us for an unbelievable trip to a part of the world rich in history and culture.  We are partnering with Captain Valerie Winegard w
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Island Dreamer Sailing · 5M ago

Rare Christmas Week Sailing Charter Opening

Margie and I are currently open for a Liveaboard  sailing class in the Florida Keys for a couple or family starting the evening of  Christmas Day till after New Years. You can take advantage of our current special on an inclusive six day trip for two for $3,972.  Time to break out your shorts and [.
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Island Dreamer Sailing · 7M ago

Our Article about Sailing in Biscayne Bay

Captain Margie and I wrote an article for the American Sailing Association October 2011 Newsletter; Featured Charter Destination An Easygoing Exploration of Biscayne Bay By USCG/ASA Captains Margie and Harold Ochstein On the southeast edge of Florida at the foot of the modern, vibrant city of Miami
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Island Dreamer Sailing · 8M ago

BSA Eco-Adventure Comments

I can’t help but enjoy what two scouts from Minnesota  had to say about our last trip of the summer season; Dear Captain Harold, Thank you for being my captain on the Morning dance sailboat. I really liked swimming with the mako sharks and snorkeling at the reef.I liked the Led Zepplin music you let
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Island Dreamer Sailing · 10M ago

Colour My World, or Sailing With Travis McGee

What’s more fun than sailing the islands?  Sailing the islands with Travis McGee.  Well, more to the point, with the series of John D. MacDonald novels that made men want to be Travis and women want to posses him. The Travis McGee series is for the “salvage consultant” among us who likes to take “hi
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Island Dreamer Sailing · 11M ago

Profile: Captain Margie

My sister-in-law, Margie, is co-captain of Island Dreamer.  She has been married to my brother, Captain Harold, for 32 years. Margie’s interest in sailing began when she was a student at Balboa High School in the Panama Canal Zone.  There, she was a member of a young adult group affiliated with the
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Island Dreamer Sailing · 12M ago

Review from Couples Sailing Class

Within several days of hands-on experience and your non-threatening methods, though, we realized that both of us should attempt certification. We both ended our week with basic ASA certifications for Keelboat Sailing 101 and Coastal Cruising 103; and Herb, for Bareboat Chartering 104. Your attentio
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Island Dreamer Sailing · 1Y ago

What to Bring With You on Your Sailing Adventure

Sailing is an easy-going, laid-back, and totally groovy experience.  Be sure to bring items that will make your life aboard even more relaxed and easier – for you and for your fellow travelers. Duffle bags or soft-sided suitcases – this is not a Samsonite situation. Sneakers or deck shoes – now your
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Island Dreamer Sailing · 1Y ago

Profile: Captain Harold

Ok, full disclosure, Captain Harold is my brother or, if we’re being technical, he’s my half-brother. What you need to know about Captain Harold, or “H.” as I call him, is that even though he appears to be carefree and laid-back, he is actually very serious and cautious. H. is the oldest of 4 childr
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Island Dreamer Sailing · 1Y ago

Sailing, South Beach Style

Here’s  what I learned while visiting Island Dreamer last week in South Beach.  There is so much to do! Now, I will be the first to admit:  I don’t get South Beach.  I don’t know what they actually do there.  But, they do have a lot going on. Let’s start with the “vapor fans”.  As [...]
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