Where to begin?

Amy’s questions

My husband and I are very serious about eventually enjoying the cruising lifestyle.

• We are presently up against many challenges, least of those is not having any experience sailing. We live in central Ohio, therefore our opportunities to learn to sail are fairly limited.  I have done some extensive research about sailing and have decided that we just need to take a week long certification class and get that taken care of.

• We are both 40 and in 5 years our children will all be out of the nest.  I have always been a “fly by the seat of my pants” kind of person, so my fear is minimal, but my husband is an organized, bit conservative fellow. Do we sell our home and all of our belongings and just jump right in, or do we keep those assets just in case?

Where do you feel the best places in the world are to sail? How do we know what is required for different countries? We have been researching the Caribbean, but I love Bali and Thailand too.

Thank you very much for your time.  Any advice will be immensely appreciated, as we are feeling a bit lost and overwhelmed right now.


Gwen Hamlin answers.

Gwen HamlinDear Amy!  Wow!

What you are asking is what everybody wants to know, and those of us who have “been there/done that” have answers…but not necessary the formula that will be what you end up following.

That, of course, is what Women and Cruising and my column Admirals’ Angle are all about, trying to present a bunch of building blocks so you can see how others have done it and pick and choose the bits that will work for you.

Let me just say that coming from the mid-West is not the ultimate handicap.
 Photo: Shelly Tucker, s/v THREE MOONS
In 1989, Shelly & Randy Tucker, from Tennessee, chartered with Gwen Hamlin on s/v WHISPER. 8 years later, they bought their own charterboat, THREE MOONS, and …they are still in the yacht charter business!.
Photo: Shelly Tucker, s/v THREE MOONS

My husband got started with Hobie 16s on a reservoir in Indianapolis that was so small he could tack down it in 15-20 minutes (hence the name Tackless for his first and second monohulls  because (heh heh)..he tacked less!)

When I was in the charter business, my very first season, I had a young couple from Tennessee book my boat.  Where they got the bug from I don’t know, but we had a grand week, after which they went back, bought a small fixer-upper to sail on a local lake, sold it, stepped up to a bigger fixer-upper…and so on.

Then they bare-boated in the Virgin Islands, then they started organizing bareboat groups to the Virgin Islands, and then nearly eight years later, they actually bought their own charter boat, a huge Irwin 65, and came to the islands as I was leaving to go cruising in 1998/9.  There are still at it!  (See

So a crewed charter, where you can fully enjoy the lifestyle but also benefit from learning one-on-one from an experienced captain (be sure to make clear to your charter broker what you hope to get out of your charter!) is a very valuable education masquerading as a vacation.  Particularly if you have curiosity about the charter business yourselves.

Women on the Water Week. Photo from the Bitter End Yacht Club website
Women on the Water Week.
Photo from the Bitter End Yacht Club website

You might also want to look into  Women on the Water Week, a favorite project of Pam Wall’s, which takes place at Bitter End Yacht Club (Virgin Gorda, British Virgin Islands) in the summers.

Many women feel that having the chance to learn sailing fundamentals on their own, away from the shadow of their usually stronger, often more experienced partners makes a huge difference.  Husbands just can’t stop being protective and chivalrous and wives tend to defer in areas they aren’t knowledgeable about.

Take a course together later, maybe even someday on your own boat!  Having an instructor oversee the working systems the two of you will need to work out would have to make that whole process go more efficiently,  I had Kiwi friends who did just that on their boat before leaving New Zealand northward on their first cruise.

Do we sell our home and all of our belongings and just jump right in?

Finally, re destinations and jumping right in…go cautiously to start; hedge your bets to whatever extent your finances will allow.  Don’t sell out your house, if you live in an area it will be hard to come back to if you feel strongly about coming back there.  But your kids will be grown and may not settle where you were anyway, so often selling leaves you more flexible for future choices.  I’ve written about this process a couple of times in my Admiral’s Angle columns.

But regardless, take at least one year in a cruising ground from which you can realistically return, both to shake yourselves down and your boat.  For the East Coast that is usually the Bahamas or the Caribbean, and for the West Coast that is usually Mexico or Central America.

You know, cruising is a wonderful lifestyle, but it doesn’t turn out to be for everybody.  I’ve just been talking with a late 50s couple who’ve just returned from 18 months up the East Coast.  Perhaps it was just bad luck, but the weather seemed to be against them continuously.  Stopovers were more expensive than they anticipated, and it turned out the two of them expected different things from their destinations.  Plus they stayed in the US, which to me is a different kind of cruising than I experienced.

We have many other stories to read on, particularly on the “12 questions to 12 sailing Families” page.  In fact Family #12 is a family that left with two teenagers!  Perhaps you will find inspiration to go NOW!

Where do you feel the best places in the world are to sail? How do we know what is required for different countries?

World_Cruising_DestinationsFor cruising info, most of us get basic info from reference books and/or (these days) websites.  Tons of that info is available on on the page called Resources.  On that page, under Reference Books, are some links to recommended reading.  Anything by Jimmy Cornell will give you info about places, particularly his new book World Cruising Destinations.

Also, one of the first things you should do is join the The Seven Seas Cruising Association (SSCA) as an Associate Member.  This gets you their monthly Bulletin which will immerse you in the real world of cruising.  SSCA has conventions (called Gams) around the country several times a year where you will meet real cruisers and partake of good seminars.  SSCA has taken that a step further with their Seven Seas U (SSU), an online cruising university.  Excellent webinars (including ours) are available right in the comfort of your own home.

Finally, favorite places will be different depending to whom you speak.  Some people love the Caribbean, we loved Mexico and Central America (which were not even on our original plan!), others love the history and cultures of the Med.  The South Pacific and Indonesia and Thailand are also great destinations, but they are BIGGER COMMITMENTS (esp with what’s going on in the Middle East),  and, frankly, the weather is not as pleasant as the south sea tales make out!

I once had a mentor who always said, with reference to those of us living the boating life, “We have a responsibility because we are living other people’s dreams.“  What HE meant, was that we had to live the life to the biggest, fullest extent, and never cast a critical word.  But I, on the other hand, have always felt that trying to be realistic – to share some particulars of the not-so-great with the great – is the only fair way when asked for counsel on such a huge life choice.

So, hope I’ve been helpful.

Good luck,
Gwen Hamlin

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2 comments to Where to begin?

  • Rich

    Amy, my wife Donna and I moved on to our Morgan 38 in 1978 here on the San Francisco Bay. After 10 years we had lots of experience sailing in a variety of conditions and had done some bareboat charters in the Caribbean. We were comfortable with the smaller, closer quarters of living on a sailboat but didn’t have any cruising experience. We felt it was important to get some experience actually cruising before committing ourselves to a retirement of sailing. We decided to take a six month leave of absence and sail the west coast of Mexico. It took us a year to prepare but in the fall of 1988 we set sail for Mexico. After the trip we had a better idea of what we wanted and knew that yes, cruising was a lifestyle we would enjoy. Acquaintances of ours had focused their retirement on cruising without any real experience and after six months found that was not for them and returned to land. We spent the next ten years getting prepared both boating-wise and financially to go cruising. We bought a Catalina 42 and equipped it for long distance cruising. In the meantime Donna skippered our home in weekly races on the bay.

    When we first moved aboard we sold our three bedroom, two bath house on a corner lot with a swimming pool and put the furniture in storage until we decided it this was going to work for us.

    Gwen’s suggestion of doing a chartered cruise is excellent. It will be an enjoyable and valuable learning experience.

    The realities of cruising will be very different from the dreams, bad weather, equipment failure away from easy access to replacement parts etc. but the experiences of what you will see and the people you will meet will stay with you forever and be memories you will always cherish.

    We met many cruising families and the children had wonderful experiences. I think one of the most interesting arrangements we cam across was a family where they had an agreement that if any one person decided they wanted to stop that they would stop cruising. The kids got to experience the responsibility of being on watch and responsible for the safety of the ship and crew in addition to seeing places they had only read about.

    Cruising isn’t for everyone so you need to take some tiny steps first to see how you and your crew react to this lifestyle.

  • Sailing Crew Member

    “All journeys have secret destinations of which the traveller is unaware.” Martin Buber

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