From Backpacker Working For $3 An Hour To Sailor With An Online Business

My monthly Extraordinary Lives series is something that I’m really enjoying doing. First up was JP Livingston, who retired with a net worth over $2,000,000 at the age of 28. Today’s interview is with Kach Howe. She has been to over 100 countries and all 7 continents. She is now sailing the Caribbean with her husband…

Michelle Schroeder-Gardner

Last Updated: June 4, 2023

Disclosure: This post may contain affiliate links, meaning if you decide to make a purchase via my links, I may earn a commission at no additional cost to you. See my disclosure for more info.

From Backpacker Working For $3 An Hour To Sailor With A Digital BusinessMy monthly Extraordinary Lives series is something that I’m really enjoying doing. First up was JP Livingston, who retired with a net worth over $2,000,000 at the age of 28. Today’s interview is with Kach Howe. She has been to over 100 countries and all 7 continents. She is now sailing the Caribbean with her husband and cat.

She’s not retired, though – she’s still working!

In this interview, you’ll learn:

  • How she has been traveling for 5 years and has traveled to 100 countries;
  • How she now lives on a 1971 Finnrose 37 sailboat;
  • How she affords to travel;
  • How they taught English in Peru for $3 an hour and how that motivated her to find ways to make more money;
  • How much sailing costs them.

And more! This interview is packed full of valuable information!

Her and her story have been featured on CNN, BBC, Yahoo Travel, Forbes, Cosmopolitan, and more!

I asked you, my readers, what questions I should ask her, so below are your questions (and some of mine) about Kach’s story and how she has accomplished so much. Make sure you’re following me on Facebook so you have the opportunity to submit your own questions for the next interview.

Related content:


From Backpacker Working For $3 An Hour To Sailor With A Digital Business

Tell me your story. Who are you and what do you do?

My name is Kach and together with my husband, Jonathan, I have been traveling all over the world since May of 2013. For the past five years we have been traveling constantly and living on the income from our own online businesses, primarily through our travel website Two Monkeys Travel but we have since expanded into several other areas including lifestyle, travel coaching, visa applications and flight reservations with our second website,

I am originally from the Philippines but I moved to Kuwait after finishing university to pursue a new career and eventually to enter the Oil & Gas industry. After about three years I moved to Erbil (Kurdistan) in northern Iraq in search of bigger opportunities and a more adventurous life, which is what led me to meet a whole group of international expats and English teachers through the thriving Expats community there.

I’ve also met a lot of backpackers & hitchhikers, their stories of travel and the freedom of their nomadic lifestyle afforded them to won me over and shortly after I began planning my own travels, starting with backpacking around Southeast Asia. It was on a few weeks into this adventure that I met Jonathan, a British backpacker in his late twenties (he was 27 years old while I was 24 years old that time) who had left his architectural career in the UK to pursue a life of travel. Neither of us had any firm plans other than to travel and find ways to keep traveling so we decided to travel together.

We have been doing exactly that for five years now and it brought me to 100 countries in 7 continents (including Antarctica). In May of 2017, we traded land and air travel for a life at sea, spending eight months for Jonathan (and 4 months for me) living aboard and renovating a 1971 Finnrose 37 sailboat, Empress, which is now our first real home together.

We just started our new adventure on February 25, 2018, we’re now slowly sailing around the Caribbean (currently in the Bahamas) with the two of us as crew of our sailboat with our newly adopted kitten named Captain Ahab.


How many countries have you traveled to? Did you used to live out of a suitcase?

We have each traveled to over a hundred countries in all the 7 continents (including Antarctica where we spent 16 days for our Honeymoon trip in 2016), seventy of which have been together. Now that we are sailing the pace of travel and life in general has slowed down considerable, but we are still adding new countries as we sail around the Caribbean.

For the first two years of travel we lived entirely out of our backpacks, occasionally stopping in place for long enough to rent a small apartment and work to earn more money to keep traveling. As Two Monkeys Travel, which started as our small personal travel blog, continued to grow in readers and income our travel style started to transform as well. We began working with luxury hotels, tour companies, airlines, brands and even national tourism boards who would hire us to promote their property, tours, services and products. We got paid on per diem or per project basis aside from the fully-expense paid trips (hotels, tours, flights, etc.).

As this happened we exchanged our backpacks for suitcases, our baggy hippy pants for nicer clothes and invested in new laptops and camera gear to improve the quality of work we could offer new clients.


How did you afford to travel that way?

When Jonathan and I first started living and traveling together in July 2013, we earned money by teaching English in Hanoi, Vietnam. Over the course of almost 7 months we saved over $10,000 which we used to fund our travels around India and teaching certifications in yoga and Ayurveda massage therapy, our short trip to the Maldives and a family visit to the UK. We made our funds stretch even further by traveling cheaply and by volunteer working in hostels in exchange for accommodation where we could.

When we flew to Peru on July 2014, we were down to our last few hundred dollars so we volunteered in a hostel in Ollantaytambo near Cusco, teaching yoga in the garden for donations and offering and mobile massage business to passing tourists. This business consisted of nothing more than a borrowed massage table, pushed around town in a rusty old wheel barrow and some oils we had carried from India, but it was enough for us to save the money we needed to buy our bus tickets to Arequipa and start renting an apartment so that we could start teaching English again! We were fortunate to find a 2-bedroom fully-furnished apartment that was only $600/ month, we converted the spare room into a massage therapy room, investing our last hundred dollars on a new massage table and a small rice cooker to heat oils in. We quickly built up a list of regular clients, both locals and expats, which helped to supplement our low teaching income.

It was during this time that we started our travel blog Two Monkeys Travel and within a couple of months the story of our alternative lifestyle started to get picked up and featured by major publications like Forbes, Business Insider and Cosmopolitan. These features, combined with long hours working in our small apartment, rapidly grew our audience and with three months our online income from affiliate marketing, brand partnerships and sponsored content was enough to let us quit our teaching jobs entirely.


From Backpacker Working For $3 An Hour To Sailor With A Digital Business

Can you tell me more about teaching English? Was that a full-time income? Can anyone do this?

When Jonathan and I first started teaching English we were living together in Hanoi, Vietnam where teaching is very well paid in comparison to the local cost of living. We earned a minimum of $20 USD per hour in a city where you can eat a good meal for $3 and a large beer cost as little $1!

In theory the only requirement to be an English teacher in Vietnam is fluency in the English language and an online TEFL (Teaching English as a Foreign Language) certification. In reality if you have a passport from a country where English is the primary native language then you can get away without the certification and even command a higher salary. Each country is very different and not all pay as well as in Vietnam.

As soon as we started teaching English in Peru our salary dropped to about $3 USD per hour, which with twice the cost of living was hard to live on at all. However in hindsight, it was partly thanks to our low income that were motivated and inspired to be more creative in finding other ways to earn money and this definitely contributed to the success of our online work.

Related content: How To Teach English From Home And Earn $14 to $26 An Hour


Why did you decide to start sailing?

While traveling the world living out of a backpack or a suitcase is adventurous and exciting we both started craving more of a balance to our lifestyle. Running a business that demanded our daily attention meant that we were traveling and exploring by day, then working until the earlier hours at night. By the time we got married in the UK in August 2016 we both agreed that we were ready for some kind of a home. The idea of sailing had come along much earlier, when we spent five days traveling from Panama to Cartagena via the San Blas Islands by sailboat in May of 2015.

We were still backpackers at that point and only had a few hundred dollars at any one time, but Jonathan decided then and there that he wanted to buy a boat and sail around the world. In May 2017, his dream of living on a boat and our need for a place to call home came together when we found Empress sitting neglected in a boatyard in the Florida Keys. The best part of it all was that we could could still travel wherever and wherever we wanted!


From Backpacker Working For $3 An Hour To Sailor With A Digital Business

Tell me more about your sailboat.

Empress is a 1971 Finnrose 37 sloop, 37 feet long with a 12 foot beam and built in Finland for the rough waters of the North Sea. Back in her day she would have been one of the best blue water cruisers available with an over-built fiberglass hull, modified full keel and oversized standing rigging.

Due to her age and less-than-perfect condition we spent around $50,000 from buying to getting her back into cruising condition over the course of eight months while moored in Boot Key City Marina in Marathon, Florida Keys. Aside from paying other people for our bottom painting, hauling out, rigging etc, Jonathan did all the necessary structural and mechanical repairs to make her safe for open water, then set about revamping her interior to turn her into a bright and comfortable home (she now looks like a Miami Beach House Floating Home which is just perfect for our taste).

All of the old wood-veneer was repainted in bright colors and new linings were made for the floors, ceiling and interior hull linings. We added a solar power system, a fridge, freezer and new communications and GPS navigation equipment. We even removed the old marine toilet and replaced it with a new composting head, removing the nasty smells often associated with toilets on boats! Now Empress is ready to sail all over the Caribbean and could even take on ocean passages like the Atlantic and the Pacific.

We also spent quite a bit of money on buying a brand new Viking Liferaft and made sure to purchase our annual Marine Insurance.

You can find more about our sailboat here and the projects we did:


Do you plan on sailing around the world? What experience do you have sailing?

Jonathan flew to Turkey in September 2016 to take a RYA Day Skipper course in order to learn the basics of handling and managing and boat and its crew, but neither of us had any real sailing experience. We plan on sailing around the Caribbean for the next year or so, before crossing the Panama Canal to get ready for a Pacific Ocean crossing. Whether we plan to continue with Empress after the Caribbean is still up for debate. She’s a strong and capable boat designed for ocean crossings, but just as our travel style evolved in the early days we can already see what type of sailors we want to be long term – very comfortable ones!

Although we considered newer catamarans for a while, we recently came across a boat that changed everything for us, the NEEL 51 trimaran. It’s a luxury performance multihull that provides all the modern comforts, space and stability of the best new catamarans with all of the sailing benefits of a monohull. Empress is definitely the right boat for us at the moment and probably for the next year as she’s tough enough to take our rookie mistakes and simple to repair, but when it comes to a long term home we know that we’ll be looking for a luxury upgrade by 2020 before we do our circumnavigation!


How will you work and sail? What will you do for internet?

We’ve been dealing with the challenges of traveling and staying connected for  a few years now, so we know that there’s always a way. In reality when sailing around the world, much of the time is spent at anchor close to land and therefore in range of cell towers so we can always get a local sim card or find WiFi on shore.

In the Caribbean we will rarely, if ever, make any crossings longer than two days, so we can just plan our work around our travel plans just as we have always done.

But the key here is that most of our work is outsourced to our full-time team excluding the Travel Coaching that I have to personally do which only needs 15 to 20 hours a week.

I actually recently wrote about that question on our Facebook page –


From Backpacker Working For $3 An Hour To Sailor With A Digital Business

What’s an average day like for you?

The beauty of this lifestyle is no two days are ever the same, even when anchored in one spot; the wind and the waves takes care of that! We tend to wake up around sunrise which is when I get up to feed our kitty cat, then take care of emails, some coordination with my assistants or attend to a coaching client. I also started practicing Hatha Yoga either early in the morning or during sunset time.

Jonathan stays in bed a couple of hours longer then sits around drinking coffee on the deck for another hour while deciding what he’s going to for the rest of the day. If we have any writing or specific campaigns to work on then we’ll work on that from about mid-morning into the afternoon, then either leave the boat to explore or get on with one of never-ending list of boat projects!

Today is the perfect example; once we finish writing this interview we’ll head over to shore with some sailing friends to have a bonfire on a quiet beach nearby.


How much does sailing cost? I know this is a loaded question!

It’s important to break this question up into two parts; buying and preparing a boat; and actually sailing.

The cost of buying a boat can vary hugely, but in our case, we spent over $50,000 on our S/V Empress to get her ready (boat parts, rigging, electronics, etc.) plus the new projects we had to do after surviving Hurricane Irma in Marathon, Florida Keys! That’s also not unusual if you take the belt and suspenders approach of replacing lots of important components and making improvements, plus adding lots of comfort. 

Once you have the boat ready the cost of actually sailing it is much lower, especially if you spend most of your time at anchor instead of marinas and do most of your own cooking, catching your own fish, etc.

The month before leaving our mooring ball in Boot Key City Marina, we also did some provisioning: for food, spare parts, fuel, medicine, personal supplies, etc. which cost us around $5,000 aside from buying our Viking Liferaft, Marine Insurance, Sailing App Membership, which cost us around $4,000.

Here’s our costs for the past month here in the Bahamas in the order they happened since we left on February 25, 2018, if we are only at anchor:

  • Bahamas boat entry permit – $300
  • Local Sim Card and internet – $150 (already used 50GB on BTC)
  • Fresh coconut bread x 2 – $10
  • Ice Bag – $4
  • 20 gallons diesel fuel (Bimini) – $120.48
  • Propane Tank refill – $28
  • 5 Gallon drinking water – $5
  • More bread – $4
  • 3 x Oil and Fuel Filters – $100
  • Breakfast out – $21.38
  • Dinner Eating Out – $200
  • Seasickness tablets – $47.44
  • Big Grocery Shopping in Nassau (Meat + Cat Food) – $305
  • Taxi in Nassau – $23
  • 5 Gallons diesel (Nassau)- $21.35
  • Zinc for propellor shaft – $41
  • 1 Liter Coconut Rum – $16
  • 1 x beer, Crab Cakes and Fries Eating out – $23
  • Navionics Caribbean App – 50 GBP (we have UK account / so $71)

Total cost Feb 26 to March 29 – $1,490.65

In reality, we did stay in marinas when we first arrived in the Bahamas as bad weather prevented us moving on and we had some improvements and modifications to make after our first big sail across the Gulf Stream. We stayed in 3 different Marinas for : Bimini, Nassau and South East of New Providence Island, the rates vary from $1/ foot in Bimini to $2.5/foot in Nassau + taxes + the required charge for water.

  • Bimini BlueWater Marina -$319
  • Nassau Yacht Haven – $264.45
  • Palm Cay Marina – $446.08

Total Marina Cost in Bahamas = $1,029.53

Total Cost including marinas – $2,520.18 for 35 days of cruising since we left Florida Keys on February 25, 2018

So now that we are living entirely at anchor sailing is much cheaper. Also, many of those costs during the first month were to stock up on items that will last several months or longer, such as the oil and fuel filters, propeller shaft zinc, propane refill (1 month). Our diesel costs and steadily decreasing as we get better at sailing and use the engine less.

It’s also worth noting that our internet usage is very high because we use it to run our business, therefore it pays for itself. Most of our friends only use about 15GB of data per month in the Bahamas but I already used 50 GB and still need more for our next few weeks left here.

We also did a lot of food provisioning before we left the States, mostly dry and canned food aside from cleaning materials, snacks, my Asian ingredients that will likely last us a year. When we arrived in Bimini Jonathan converted our built-in icebox to a powered fridge using equipment we had bought in the States and not had time to install. We then had a top loader fridge, big enough to fit a fully grown human inside, that needed to be filled with fresh meat, chicken and vegetables – the $305 shown above.

As you can see the cost can vary wildly depending on how you do it, but I hope this gives some idea of how much sailing and living aboard can cost!

I know that we can lower our costs eventually but since we’re only a month since we started our adventures, we’re still learning!

Note: Our business expenses is excluded in this computation.


How do you handle health insurance and health care?

Unlike others, we don’t have a medical or life insurance. We’ve been traveling the world full-time since 2013 and what we have is a Travel Insurance that will cover us on any medical and non-medical emergencies (missed flights, theft, etc.).

We take care of our healthcare in the same way that we always did when we travelled on land. We both have comprehensive travel insurance which covers all of our health needs and emergency treatment, plus medical repatriation to our home countries if needed. We don’t go to see a doctor for regular checkups, but we just keep ourselves healthy and if we have any accidents we need to know what emergency services are available nearby.


Do you think you’ll ever live in a more traditional home in the future?

We have considered the idea of living in a home on land some day and that still may happen. We have even thought about buying a piece of land in Greece where Jonathan can build us a house on a hill overlooking the sea, but now that we’re actually sailing this seems far too restrictive.

We would have something tying us in one place and tying up a large amount of money at the same time. We would rather invest that money in a bigger, more comfortable boat that can take almost anywhere we choose, our next goal is to buy a NEEL 51 Trimaran instead.


What’s one place that you can’t wait to visit on your sailboat?

When we first took that sailing trip from Panama to Cartagena, Jonathan proposed to me on a tiny little island in San Blas. Part of our journey with Empress will be to sail back to the San Blas with our own boat.


Lastly, what is your very best tip (or two) that you have for someone who wants to reach the same success as you?

To say that you simply have to believe that you can is too much of a cliche, but it’s certainly an important part of it. What we still feel is the most important part of our own process is to constantly learn new things and to always build up a bank of skills that you can use to support yourself anywhere in the world.

At some point though you simply have to get out there and just try whatever it is you’re thinking of doing, because if we had not put ourselves in positions where life became difficult then we may not have come up with the ideas that brought us to where we are today.

Always remember, DREAMS DO COME TRUE.

What questions do you have for Kach? Are you interested in living a nomadic life?

Michelle Schroeder-Gardner

Author: Michelle Schroeder-Gardner

Hey! I’m Michelle Schroeder-Gardner and I am the founder of Making Sense of Cents. I’m passionate about all things personal finance, side hustles, making extra money, and online businesses. I have been featured in major publications such as Forbes, CNBC, Time, and Business Insider. Learn more here.

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  1. Love this! So inspiring.

  2. What an interesting life! I don’t think I’m adventurous enough to live a nomadic lifestyle, but I still love reading stories about people who are able to pursue their dreams in unconventional ways. Thanks for sharing!

  3. Victor

    Who is your travel insurance provider and how much is it? Most providers will require you go “home” and not make trips longer than 30 or 90 days.

  4. Janet

    I started sailing last summer and it’s been my dream to sail around the world one day. It would be my dream to live on a sailboat one day!

  5. Janita

    Amazing story!! Teaching English in Peru actually sounds amazing for how little they were making, it was probably an experience they would never forget. Such an inspiring story, and yes, dreams really do come true!

  6. Great story – loved reading about other sailors that are enjoying the travelling life!

    My partner and I have been living and travelling on a sailboat (1974 Dufour 34) in Northern Europe since May 2017 – we’d love to get over to the Caribbean at some point in the future 🙂

    I used to teach in the UK before we left but found it incredibly stressful and I didn’t have a life doing it – how did you find teaching English abroad? Part of me would love to have a go but I currently have bad memories of teaching!

    We’re always looking to find new ways to make money online to help fund our travel long term. So far I’ve set up a publishing company and have published a number of books that are available on Amazon. Love seeing how other people do it too!

  7. These are my favorite series of yours. Keep them coming. They are so inspiring.

  8. Janell Kroeger

    I love their story, very inspiring!

  9. Brandon at

    Such a great story and very motivational. Sailing around the world is definitely one of my dreams. I love to hear about people who are actually succeeding at it while still finding ways to generate the funds to keep it going!

  10. This is possible for anyone who takes time to invest in their ability to prosper as a “side hustle millionaire,” by taking a leap of faith into entrepreneurship and do the transformation business work. Acting off of a thought will put anyone in a financial position years later to benefit from their business by never having to work for an unthankful employer again a day in life.

  11. I have enjoyed reading their blog for a couple of years now! Great people!

  12. Wow, this is an amazing story. Thanks so much for sharing your story Kach, and for your part in putting it on your blog Michelle. I have dreams of doing this type of adventure living as well someday, but in an RV on land instead of a sailboat on water. I am very thrifty and enjoyed the part where Kach shared how much it costs for them to live this lifestyle. Thanks for the inspiration that dreams can come true!

  13. Her photos are so dreamy. However, if this were me, the photos would be of me getting motion sickness off the side of the boat! I’m so jealous!