top of page


Have you ever wondered what it’s like

to cross an ocean on a tiny sailboat?


What it’s like to leave your career

and really sail off to the South Pacific?

ing 1


Rob and Dee Dubin- mid Pacific - 2,000 miles til landfall in Fatu Hiva, Marquessas

  • How do I add a new question?
    To add a new question go to app settings and press "Manage Questions" button.
  • How many countries did you visit?
    Counting all the countries we sailed to and nearby countries we land traveled to plus the countries we visited while making sailing movies for The Travel Channel we have been to just over 100. The UN lists 195 countries in the world.
  • What’s the worst storm you were ever in?
    We really only had 3 bad storms in 17 years at sea. One each in the Pacific, Indian and Atlantic oceans. Each time we had waves about 25’ high and 50 mile per hour winds for about 36 hours. In those instances we gave up staying topside and standing watch and just lashed ourselves in our bunks…looking out the companion way every now and then but hard to see beyond the boat stern.
  • How did the two of you get along in such a small space 24/7 for weeks at a time?
    This is one of the most common questions we get and it is often asked by couples who have been married for some time. Eventually Dee and I decided to sit down and write out some of our relationship strategies. If you would like to download our suggestions please click here.
  • Tell me some weird facts about sailing?
    It is estimated more people have climbed Mt. Everest than have sailed around the world. When it is really rough at sea and you lay in your bunk you can feel your internal organs sloshing around in the cavity of your belly. Despite the fact that we lived on our boat in the Southern Hemisphere for almost 5 years we never quite got used to looking up and seeing the Southern Cross instead of the Big Dipper and the North Star.
  • What about pirates?
    When we started cruising most stories about pirates were generally overblown and there were only a dozen or so incidents a year. However today in the Caribbean there are over 120 incidents a year of locals attacking yachts for money or to steal electronics. We also sailed up the notorious South China sea with no problems but off the Horn of Africa near Somalia piracy is a very serious issue. This is where the Tom Hanks true story movie “Captain Phillips” took place at the same time we were there. Transiting the area was very scary and we heard on the radio a boat only 20 miles from us being attacked. In some incidents sailors were taken hostage and it did not end well.
  • What was the name of your boat?
    Naming a sailboat is a bit like naming your children. You pour all the promise and hopes for the future into the name. We named our boat Ventana- which means window in Spanish as she was our “window to se the world.”
  • What’s the most unique experience you had?
    Rob: Actually too many to count- sharing our lives with people in remote villages that rarely see outsiders. Being the guests of honor at 3 different feasts in Fiji - one attended by over a hundred villagers and another where they had a young girl fanning us constantly just in case a fly might disturb us. Dee: In many places I would be doing our laundry at the river’s edge pounding our clothes on the rocks with the local ladies. It was always a fascinating exchange. Or having a market lady pantomime how to cook some favorite dish using a vegetable I had never seen before.
  • Did you ever encounter a hurricane?
    In our very first year of sailing we spent the winter in the Bahamas but left for the US to get out of the Hurricane belt. We were all the way up north in Martha’s Vineyard off the coast of Massachusetts and were hit by a hurricane. We had 100 mph winds but our boat managed fine because we took so many precautions. Others nearby were not so lucky.
  • What was your favorite place?
    Dee answers this one. “Favorite place… easy, the next one!” Really, we learned each place was unique and to be open to the experience. That was the amazing reality of our situation, each day brought new experiences so keeping present was not just important but necessary. When I have reflected over the 17 years if I had to chose I’d say Thailand. Wonderful country with Buddhist foundation. Our Thai friends would often greet us with the question, “are you happy today?” Happiness and sharing are primary values lived each day.
  • What was the hardest part of your trip?
    Constantly saying good bye to people who had become part of our lives and we a part of theirs?
  • How did you give back while you traveled?
    We always carried school supplies to give to kids, fishhooks and tools for the men and sewing supplies for the women. We helped build the very first school one village ever had in a remote jungle up a river in South America. In Indonesia we started a scholarship program to help young women and a few men go to college. The program is in its 13th year now and we have put 29 kids through college.
  • What was the most amazing natural wonder you saw?
    Rob: I scuba dove on an undiscovered reef off an uninhabited atoll in the Pacific. I’m sure I am the only person EVER to see that spot. We also swam with dolphins in the wild and watched two dolphins mate in the Red Sea. Dee: Snorkeling with grouper and parrotfish that were as big as I was. Night scuba diving.
  • What sea creatures did you see?
    We snorkeled within a few feet of a blue whale in the Caribbean and dove with sharks many times. Our closest encounter was when Rob had to kick an inquisitive shark in the nose.
  • Did you ever see the green flash?
    We’ve seen the green flash many many times at sea- they say that’s a sign you’ve met your one true love.
  • What was the best sail you had?
    Crossing the Pacific from the Galapagos to the Marquesas Islands was 18 days and we went many many days of that passage without adjusting a single sail.
  • Do you stop at night at sea?
    No you sail 24 hours a day and trade off with one person on watch and one sleeping.
  • How long did you stay in each place?
    Some places like Thailand and Australia we stayed for several years exploring. Some Caribbean Islands we spent months or several months at a time year after year. Other places we might only stay a few days and move on. We never planned far ahead instead just preferring to go with the flow and see what possibilities each day held.
  • How did you afford to retire at age 42?
    The short answer is just saving and investing as anyone can do. After getting asked this question so many times I’ve put together a bit of financial information and personal advice that might serve as a guide to others. If you want to download a pdf with an explanation of how we retired early and invested our funds so we could stay retired click here.
Get in Touch
Fill out this form to send us feedback or get links for our downloadable pdfs

Thanks for submitting!

bottom of page