Harold Ochstein

Time for shrimp cocktail and a glass of wine

Thanksgiving Sailing Special in the Florida Keys

Join us this Thanksgiving and take advantage of a wonderful special price of a 5 day all inclusive live-aboard sailing trip for 2 people for only $2,990.  Families also welcome (extra person charges apply). Spend the night of your arrival at no extra charge. Come anytime between November 19th through December 1st for a great — and […]

Margie and I captaining Heritage of Miami in calmer conditions

Should the HMS Bounty have stayed in port?

Our sympathies go out to the families of anyone lost on the Bounty. I am writing this only as a caution, not to assign blame or fault.  The 1st thing Margie and I do each morning is check the weather to see how it affects our cruising plan for the day and the week.  With our combined […]

Sail and explore the Mediterranean islands

Will Sailors Live Longer?

We can only hope! I was reading about the population of the Greek Island of Ikaria and how they live an average of 10 years longer than most of there neighbors (and most of us in the US). Some of their lifestyle is very close to a cruising sailor. Afternoon naps, a glass of wine with […]

Captains Harold and Margie

Why our sailing lessons are a private charter

We are at the Annapolis Sailboat Show at our Couples Cruising Classes Booth and have been chatting with a number of couples that are at different levels in there sailing knowledge. It is great to be able to offer them a sailing class where they can get comfortable sailing with each other but  also tailor lessons […]

At Sloppy Joe's in Key West

Key West, a unique and wonderful place

Margie and I spent two weeks after Boy Scout season regrouping in Key West. I ran across this description written as part of a promotional brochure for the railroad in the early 1900’s. It seems apt today; The history of the island is as romantic as it’s surroundings: it is rich in pirate lore and survived on a more polite but […]

Couples Sailing in the Florida Keys

Couples Cruising Classes at the Annapolis Sailboat Show

Come visit our  Couples Cruising Classes booth at the sailboat show from Oct.4 through the 8th. We are partnering with  other Captain Couples who also give personalized one-on-one sailing instruction geared toward couples who want to learn more about the cruising lifestyle. Look for us in “Vacation Basin” at the show. Besides our regular trips throughout the Keys, you […]

A great day for snorkeling, not so hot for sailing!

Another Summer of Boy Scout Charters is Over

Margie and I Just finished 11 weeks of sailing our two 41′ Morgan Out Island Sailboats in the Boy Scouts Eco Adventure Program.  In the last six years we have had around 900 Scouts on the various sailboats we have captained at Seabase! Each week is new and different, some are a little harder than […]

Waking up on a warm vacation

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 […]