Making Money While Sailing: Remote Jobs Beyond Freelancing

No, we didn’t win the lottery. We don’t have a secret trust fund. And despite the tropical backdrops, this cruising life didn’t just fall into our laps. We work. A lot of other younger cruisers we’ve met work too. Often between snorkel trips, surfing and sail changes there’s a laptop open. It might not be the glamorous “quit everything and drift into the sunset” life we imagined when we left Vancouver two years ago, but it beats going back north to commutes, fluorescent lighting, and meetings that could have been emails.

Finding work that fits our lifestyle was harder than we expected. Yes, some people make a living writing blogs from the cockpit or filming their adventures for YouTube, but the truth is most sustainable incomes afloat come from jobs that have little to do with palm trees or rum punches. And while freelancing works for many sailors, it’s not the only option — and sometimes, not the best one.

Why Look Beyond Freelancing?

Freelancing is great… until it isn’t. I fell into writing through a friend who referred me to a few real estate clients. That led to the occasional sailing article, which slowly grew into steady work with a couple of regular clients. Then that same friend suggested working with her virtual assistant program, and suddenly I had an entirely new income stream.

Mark’s path is a little different. He consults in IT for a variety of clients, and while his work can change in scope, it’s generally more consistent and structured than mine. His contracts tend to have set expectations and timelines, which makes them a reliable counterweight to my unpredictable schedule.

The balance works well for us. I enjoy the flexibility and can ride the wave of a busy week followed by days where I’m surfing or working on boat projects. Mark prefers the stability of knowing exactly what’s due and when. We both enjoy his steady paycheck. Together, our work styles keep generating income without either of us trapped in a traditional 9-5 or worrying where our next dollar is coming from.

But this balance isn’t for everyone.

Remote Jobs That Work From a Boat

Not every sailor is a Youtuber. Some of the steadiest, remote jobs are structured roles with a company. These offer salaries, predictable hours, and the security of being part of a team. If you’ve got a laptop, a reliable internet plan, and a willingness to adapt to your sailing pace, you can work from almost anywhere - from the calm anchorages of La Paz to the lively ones of Bocas del Toro and even the beachy bays around Grenada.

Customer support

These are a solid entry point. Companies like Concentrix and Arise hire internationally, offering shifts where you handle calls, process orders, or troubleshoot basic tech issues. The upside is reliable income and paid training. The downside is you need solid, reliable internet (and a back up should the first one fail) And a quiet place to work. That means Starlink, marina Wi-Fi, or a high-speed local SIM and no working from that local beach bar.

Finding a quiet place to work is key for customer support and online teaching.

Online teaching

This is a surprisingly portable career. ESL, or any second language, is popular, but there’s demand for everything from coding lessons to business English to test prep these days. Platforms like Cambly, Preply, and Outschool let you connect with students worldwide. Some sailors even run their own online teaching business by finding their own students. A portable teaching kit (think: ring light and a good mic) helps keep your “classroom” professional even if you’re actually in the galley. The challenge can be scheduling. If your students are in not in the same time zone, you may find yourself working strange hours.

Data Entry

If you’d rather work quietly in the background, data entry and data quality jobs might be your speed. They require minimal qualifications and don’t generally need a powerful computer. The downside is lower pay and it can be boring.

Information technology

This is a huge industry that ranges a wide spectrum of roles. Those with a technical background can command higher rates in this industry over some of the others mentioned here . Roles like cloud services monitoring, security, or network troubleshooting can all be easily done remotely. These often require certifications, but they pay well. The risk is that an internet outage can be catastrophic, so you need redundancy: Starlink plus a local SIM, plus a backup on shore.

Virtual assistant

A broad category covering inbox management, travel booking, sales coordinating, data entry, and more. You can specialize, which means higher rates, or work broadly for a single client. The flexibility is great, but time zones and client expectations can be tricky when you’re planning a passage.

Creative Passive and Semi-Passive Income

Passive income is the dream. Think about it, money rolling in while you’re out exploring. The dark side no one talks about: it’s rarely hands-off. Mark manages our investments, which means monitoring markets, adjusting holdings, and watching stocks. It’s steady but hardly “set it and forget it.”

We also run this website, which nets us… about a beer a month. Not exactly financial independence, but a nice little bonus. Other cruisers do a much better with niche websites, affiliate marketing, or self-published e-books. The key is finding something people actually want, setting it up, and letting it tick over in the background.

Some sailors rent out property on land, which can be a dependable income if you have it. Others create digital products like templates or courses. None of it is “free money,” but done right, it can fund marina fees, haul-outs, and the occasional splurge ashore.

Regardless, if you look hard enough and get creative, there’s probably some ways to make some “passive income” (back to those foot pictures maybe?).

Tools and Connectivity Essentials

Getting the job is one thing; keeping it is another. Starlink has changed the game for remote work at sea, making it possible to get high-speed internet even far from shore. In big cruising hubs like Mexico, Panama, and the Caribbean, you can likely find reliable marina Wi-Fi or local SIM cards with fast data.

We each have a main laptop and a share cheaper backup  because salt water kills electronics without warning. Same with phones. We carry noise-cancelling headsets for calls and invest in enough battery capacity to keep devices charged. And we’ve learned to work in odd spots. For the most part, we work from the boat. But when conditions allow it (and there’s wifi) we’ll treat ourselves to working on shore.

Power generation is key to keeping laptops charged.

Choosing the Right Job for Your Cruising Style

Our work mix is split: Mark keeps a structured, daily schedule while mine is looser. This lets us move when needed. I can sail while he works, then log my own hours after we arrive.

Not everyone can or wants to work that way. Some cruisers stick to weekend sailing so they can log full workweeks without interruption. Others prefer jobs that can be done offline and uploaded when they drop anchor. If you’re working while underway, you’ll need someone to share watch duties and strong stomach to avoid seasickness.

When we’re out actively cruising, we prioritize anchorages that are more comfortable for working onboard. Neither of us wants to sit on a rolling boat and try to work. When this occasionally happens, we try and seek out a place on shore to work.

Sharing space can be tricky.

You don’t need influencer fame, a YouTube channel or a booming freelancing buisiness. Structured remote jobs for sailors exist, and with the right tech setup, you can build a steady income that supports cruising.

Experiment, adjust, and find the balance between work and sail that suits your style. With a little planning, the sea can be your office and your backyard.