The cost of cruising: interview with SailLoot


How much does it cost to go cruising? How much / how long did you save in order to go? What do you spend every month as a cruiser? What about earning money while cruising? Questions along this line are among the most common that we get on Totem.

We recently had a chance to do an interview with Teddy J from SailLoot, and talk about ALL those issues. To listen in, you can stream it below, pick up on his site, or check out the SailLoot itunes channel.

Teddy has his eye on living aboard and cruising with his his wife, Megan, and their dog, Barley (yes, he likes beer!), and is asking all those questions to fuel his own planning. How much did we save put into the cruising kitty during those years of active cruise planning? What did we do professionally? How did we save money? What did we do for work in Australia? What are the expenses like while cruising? What do we spend the most money on?
Here’s the thing: everybody does this differently. His first interview, posted a couple of weeks ago, was with our friends on Delos. Brian and Karin have a really interesting story and concrete experience to share, and like us, are making cruising work with an eye on the longer term. And while we have some fundamentals in common, we have made some different choices along the way in how we’re financing, and what it costs. Every new episode from SailLoot will have new insights that help others visualize their dream and how they can make it a reality.

We answered his questions honestly and from the heart. But you can’t answer everything in an hour! I’m working on follow up posts about cruising and finances, so if there’s more you’d like to know about how we saved to go cruising, what it costs, and what we do for income- ask in the comments, or drop an email through our contact form.

Teddy was a lot of fun to talk to, and although I’m sure he would like to have gone from high school garage band to rock star, when that didn’t pan out I’m glad he hung onto the recording equipment to start up a podcast series specifically on finances and sailing. As a guy who just wants to cut the docklines too, what better way to figure it out while sharing it with the rest of the world? Everybody wins!

Teddy is a sailor, a traveler, and a planner. We fully expect share an anchorage someday, and meanwhile, we put our own challenge to him. What is it? Listen to the podcast and find out for yourself!

Financial planners know we love it when you read this on the Sailfeed website.

8 Responses

  1. Honest truth. I was just planning to ask you whether you had any blog posts addressing the question of money. Your advice is very timely for me personally as I contemplate how to keep going after I complete my Pacific Sailing adventure. After my Atlantic crossing, I went back to NY to work for a year before setting out to the Pacific. I’d like to continue on to the Indian without having to return to NY for work if possible (although I am blessed that this is an option). Am currently investigating whether I can find work in the countries that we sail through along the way. Will download the podcast as soon as I have a stronger internet connection. Thanks again. Yay!

    1. Love it Lisa (I started to type Dorny…ha!). If you’ve got questions after listening, let me know…it’s excellent input for me to write a few follow-up posts around. And yeah, I hear you, our internet access here is not “podcast worthy” unfortunately!

  2. This was fantastic — I really enjoyed listening to both of your answers, perspectives, and advice! Especially since you’re doing it with a family, cruising is some way-off-the-beaten-path destinations, and keeping a great blog while you’re at it 🙂

    I *do* hope you’ll write even more follow up posts on the topic!

    And I’m really looking forward to reading more about your Indian Ocean adventures! When you get to Galle, see if you can meet “Mangalika” in the only English bookstore in town. Her and her husband run an amazing orphanage and were some of the sweetest people we met on our journeys.

    Fair winds,


    1. Thank you Leah! I’m so excited about the Indian Ocean. I’m not sure we’ll meet Mangalika, though, since we’re hoping to avoid Galle (very poor mooring conditions) and anchor in Trincomalee instead.

  3. Great Podcast. My family and I are 3 years out but this reminded us to pick a date and just do it.. no more excuses. Thank you.

  4. The interview was so awesome and fantastic, lol! You and Jamie are an inspiration to me and my husband. We have two young kids (2 and 5) and have set a date to go cruising (June 2021 – which I’m hoping we can cut down to 2020). We live in Vancouver and are enjoying cruising the Gulf Islands and San Juans and hoping to make it up to Desolation Sound as well. Funny enough, we actually bought our boat on Bainbridge Island (we have a 27′ catalina called Lanikai) and bought her in 2011.

    I loved hearing the details about the money aspects (I am an accountant and I love spreadsheets too!)

    Just wanted to thank you for the great info and would love to learn more about trickle income. We have been debating about planning a sabbatical or just trying to go as long as we can and working as we go. It was so great to hear about your experiences with trying to work in Australia! I also found it interesting that insurance was your #1 cost. We are planning on keeping our house while we are gone, so I am also curious how you manage renters while being away. Did you hire a property manager?

    Sorry about all the questions but I can see that you have such a wealth of knowledge and are interested in sharing your experiences! Maybe one day we’ll see you on the water!!

    1. Hi Shelley- glad the podcast was helpful for you. We work hard to find competitive insurance, so you can look at that two ways- 1) insurance is really costly, and/or 2) we manage to keep other costs down really well! Re: our house: we did not plan to keep it, but then the real estate market dropped and we didn’t have much of a choice. We looked at property management services, and didn’t feel comfortable with any in our area. We are VERY lucky to have a good friend who asked if she could be our property manager: she is pretty amazing, to be honest, and we’re so grateful for her help. Hoe we get to meet you on the water someday!

  5. Loved the interview, and I’m so thankful that he started the podcast. We’re preparing for our trip now and plan to leave from the Chesapeake next summer. Our intent is to go for as long as possible, but figuring out the finances has definitely been the hardest piece. Like you, we’re saving as much as we possibly can before we leave. We also hope to make a little along the way.

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