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 lies Biscayne Bay. Sailing down the bay is your entryway into Biscayne National Park and the Florida Keys, a 170-mile chain of islands stretching off to the south and southwest of mainland Florida. The calm, pristine waters of the bay are protected from the ocean by the coral reefs and the island chain beginning with Key Biscayne. These are a few of our favorite spots; but wherever you go, the water is clear, the wildlife is abundant and the pace is relaxed.
Key Biscayne
Your journey into Biscayne Bay begins once you pass under the MacArthur Causeway. The waterfront high-rises of Miami are close by on your right and Key Biscayne with its marinas and anchorages appears on your left. You can anchor off the west side of Key Biscayne for a comfortable night in the prevailing easterlies. At the south end of Key Biscayne you will find No Name Harbor located in Bill Baggs State Park.
This is a very popular spot for cruisers waiting to cross the Gulfstream to the Bahamas. During the day tie to the seawall, or anchor in the harbor overnight. Chat with sailors from around the world, invite them aboard for a sundowner and share your stories. After walking along the park’s nature trails, take a tour of the working lighthouse built in 1825. Spend some time at the beach on the Atlantic Ocean side of the island, then stop for a drink or have dinner at the Boaters Grill. Read the rest of the article
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 “his retirement in installments”. The title of each book references a color such as: The Deep Blue Good-By, The Quick Red Fox, The Long Lavender Look, and, my personal favourite, Cinnamon Skin. You get the idea.
The books are trip through the still-developing 1970s male psyche. There’s much discussion of stereo equipment, sticking it to the ‘man’, and, of course, women. The women in Travis’ life are always, if not conveniently, unattainable.
But what makes these books the perfect sailing companion is found in the author’s detailed descriptions of Florida’s flora and fauna. It’s like having a personal tour guide, a personal storytelling tour guide, right at your fingertips.
As the plot twists and turns, MacDonald takes you through the marshes of the Everglades and the coral reefs of the Keys. These books are a terrific way to get a sense of the beach bum perspective without quitting your day job.
Adding colour to your Island Dreamer sailing adventure, Travis McGee is the ultimate companion, tour guide, and all around “Dude”.
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 Docksides are more than just a fashion statement.
- Sandals or flip flops – for your ‘formal’ outings in the Keys
- Shorts and shirts – Men, this is your chance to break out that Hawaiian shirt you got for Father’s Day.
- Skirts and tank tops – Women, this is the time to show some skin and get a little color.
- To that point, you’ll need some sunscreen, sunglasses, scarves, and hats.
- Several swim suits – one per day is my rule.
- Medications, eyeglasses, and contact lenses supplies
- Soap, shampoo and toothpaste are provided but, you’ll probably want your own stuff
- Ipod - now’s the time to create your “Vacation” playlist.
- If you have snorkeling gear, bring it. There’s lots to see underwater.
You don’t need much, but it’s always good to be prepared and not have to worry once you get there.
Now you can relax and enjoy your Island- Dreamer vacation.
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 children sired by our father. There are 3 boys and me (and, no, I didn’t get treated like a princess growing up – quite the opposite). As much as I hate to admit this, Harold has influenced us all. He has set the standard for music, quality of life, and politics for the three of us. Thanks to H., we all can ‘name the band’ when he plays a song and we will never forget the great “Standard of Living v. Quality of Life Debate” he had with our father.
He once told me, “If you don’t like the world you’re living in, create your own.” This is the essence of who Harold is: Henry Miller meets Ayn Rand.
Island Dreamer was born of this philosophy. He has successfully married his love for sailing with his business sense and achieved that elusive American dream of making a living doing what you love.
Now, it must be said, there is no Captain Harold without his wife (and my sister-in-law), Captain Margie. No one in the family can figure out why she married him, but we are eternally grateful to her.
Together, Captains Harold and Margie have created Island Dreamer and a wonderful life aboard sailing around the Keys and embarking on new adventures.
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 you wander down “the strip”, you pass through cafes and restaurants that keep its occupants cool by spewing a water vapor all over its guests. I suppose this is supposed to offer a cool comfort from the heat, but it’s a little disruptive, if you ask me. Plus, I have to wonder if the chefs and bartenders have to take “water vapor” into consideration as they prepare their “South Beach Signature Items” Still, it’s just water and something to see, that’s for sure.
So, if you’re like me, you’ll want to sit inside the actual restaurant, where they have a quaint little invention whose name says it all: “Air Conditioning”. There are no two sweeter words together in the English language. They just roll off your tongue, exuding leisure and decadence in every syllable
There are many restaurants to choose from in South Beach. You might want start with The News Café, where Versace had his last meal, or go for the more trendy Joe’s Stone Crab. You can find any type of cuisine there on the strip. Middle Eastern, Sushi, Thai, Cuban, Ethiopian, Greek, French, Italian, Belgian, Caribbean….you get the picture.
After you’ve eaten, you can walk off your meal at the many museums and shopping attractions. On one street, can get your Louis Vuitton on, while on the next block you can poke around the various museums and galleries.
The Art District also has happenings going on from street performers to independent movies – check out O Cinema for some cool flicks at a great price and help support the arts at the same time.
As I discovered, South Beach is not really the place to go if you’re looking for conch fritters and beer, but it’s definitely a sight to see, a glittering gem in the treasure chest of your sailing adventures.
When sailing throughout the Florida Keys, you want a little nosh. Fortunately, on Island Dreamer, Captains Harold and Margie have got that covered!
Below, are just a few suggestions for making your cruising experience even more enjoyable.
1. Hummus and vegetables. Cut up red and green peppers, cucumbers, and wash off some sugar peas and dip them in the hummus. This is a flavorful treat and a good way to get your daily supply of veggies.
2. Fruit and cheese board. A variety of fruits such as grapes, melon slices, and apples alongside one or two blocks of good cheese. This can be quite filling, so pace yourself.
3. Assorted nuts and dried fruits. This snack is good for that extra boost of energy.
4. Shrimp and Cocktail Sauce. Cool and tangy
5. Assorted Chips and Dips. Potato, Tortilla, or Corn chips go great with French Onion Dip, Tomato Salsa, Bean and/or Cheese dips
6. Not really a snack, but refreshing nonetheless, is cucumber infused water. Slice up a cucumber and drop into a gallon of cold water. Chill for 10-15 minutes. Quite refreshing after you’ve been out in the sun all day.
Island Dreamer happily provides these righteous goodies for your enjoyment and will also plan a menu to fit your specific needs.
Cheers!
Sailing on Island Dreamer is a blast, but it never hurts to be prepared. Below are 10 things you’ll need to bring with you on your sailing adventure.
- A Good Book. Ideally, a book that has nothing to do with your real life. Seduction of the Minotaur or Like Water for Chocolate are two excellent choices, or, on the other end of the spectrum, anything by Carl Hiaasen.
- Sunscreen. Normally, I’m anti-sunscreen, but no one is getting any younger and with the reflection from the water, the sun is stronger than your realize.
- Moisturizer. See above. Stock up on After Sun Lotion and Baby Oil.
- Music. This is key. You will need a good soundtrack for your vacation. Take the time to create a “Vacation Playlist”. Think soulful, rhythmic, and jazzy.
- Bathing Suits. As a general rule, you’ll want at least one per day.
- Sarong or Sundress. Make your life easy and buy something simple, colorful, and comfortable.
- A Cute Hat or Scarf. Unless you like the frizzy wind-blown look, you’ll need something to tame your tresses.
- Wine. Who are we kidding? Wine is good! A couple of bottles of your favourite Chardonnay or Pinot will be sufficient.
- Sunglasses. Don’t bring your best pair, and be sure to bring back-up.
- Conditioner. The sun and saltwater will dry out your hair. Leave-in conditioner can be a life saver.
NOTE: One thing NOT TO BRING is jewelry. You do not want your emerald cut solitaire going overboard. Leave your irreplaceable jewels at home.
Nestled in an out-of-the way area in the heart of Marathon is a small marina and mooring village along Boot Key Harbor. It is the home of Sombrero Marina and the world famous Docksides Bar.
The locals gather around the grand wooden bar at all hours, from breakfast until last call, listening to the radio and watching the weather reports on TV. The marina is always buzzing with activity. And when the sun finally sets, you can hear the call of Conch shells celebrating the end of the day and the promise of the night to come.
But late at night, strange things have been know to happen in the harbor, I’ve actually seen a man tow a dinghy — swimming across the harbor holding the rope between his teeth because the motor had broken down.
Late at night, it’s eerily quiet crossing the harbor over to the sail boat. It’s easy to get lost in your thoughts. The sky and water are the same shiny black ink. It’s at those moments that I often wonder where the name ‘Boot Key Harbor’ came from.
According to legend, a stylish young woman, visiting from up north, her feet tired from dancing all night at the Brass Monkey, took off her very expensive boots with 4-inch heels and tossed them one by one into the harbor during a 3am crossing. According to the story, somewhere, at the bottom of the harbor is a size 6 pair of Valentino black suede stiletto ankle boots mysteriously still in pristine condition.
Every once in a while, I think about those Valentino boots and what they must have meant to her and how she could have let them go so easily.
…at least for a week, see how it goes. Hop a flight to Miami, board Island Dreamer, and head to the Keys.
The first thing you’ll notice is how the sound of water gently lapping against the side of a sailboat will put you to sleep. Even as the sun is glistening in shards of light off the ocean, as far as you can see, it only acts as more incentive for you to close your eyes. Sounds become muted and the moments before you arrived are now a faint memory.
What you are feeling now is “Keysey”. The stress you used to feel, that panic in the pit of your stomach has dissipated and evaporated into a miasma of sunlight and ocean breeze
What’s that you hear? Steel drums or is it Steely Dan? How long has that rum drink been in your hand? (and, does anybody really care?). The warm air tickles your bare feet as you reach for that Travis McGee novel (no judgment here, it’s cool).
Dolphins are free associating with the water over to the port-side; seagulls are flying close by, laughing at them. You could get used to this.
By the time this week is up, you are a not the same person who boarded the boat. Your batteries have been recharged and nothing is a big deal.
Decision time: Can you adopt a stress-free lifestyle?

Island Dreamer sailing on a close reach
Margie and I have spent the last few days sailing the backcountry of the Florida Keys on our journey to Key West to pick up our next couples sailing charter. I am reminded once again how pleasant it is to sail along at 6 knots in 15 knots of wind and still have calm seas and not have the boat heeled over to the rails. The combination of having the sails reefed and set properly and the protection of the many small islands and shallow water makes it easy to relax and enjoy gliding through the water.
We are looking forward to spending some time before our charter with our friends Captain Holley and Captain Denny who own the Schooner Conch Pearl. They do Liveaboard sailing scuba trips based out of Key West. We got to be good friends when Margie and I were running the Schooner Heritage of Miami for the Boy Scouts High Adventure Seabase and our days off coincided two summers ago. Because they have a compressor on board to fill their Scuba tanks they are able to dive locations that diving day trip boats don’t go to in the Florida Keys Marine Sanctuary.