Liveaboard Lifestyle Pros and Cons: Is Sail Life Right for You?

Our sailing adventure began with a plan to sail for one season. One season to buy a boat, learn to sail it, and explore the Mediterranean before moving back ashore to settle down and start a family. Four seasons later, we’re still afloat, only now we have a one-year-old in tow, and we’re going to need a bigger boat.

If you’ve ever been sailing (or even if you haven’t), the dream of living full-time on a boat has a magnetic pull.

Sunsets at anchor, dolphins off the bow, and the freedom to wake up in a new place whenever the wind allows. It’s a dream that more and more people are chasing — trading mortgages and commutes for sails and salt air.

But if that’s the dream, what’s the reality? The truth is, living aboard isn’t for most people. It can be hugely rewarding, but it can also be a sparse and challenging lifestyle. A lifestyle full of highs and lows. Deciding whether it’s right for you means weighing both carefully.

Here’s our honest take on the pros and cons of the liveaboard lifestyle — from the perspective of a couple, and now a young family who’s been doing it for years.

⚖️ Liveaboard Lifestyle: Pros and Cons at a Glance

✅ Pros of the Liveaboard Lifestyle:

Freedom and Adventure

This is the real reason we do it: to carve out a life where each day is a vivid and distinct chapter… and, because the fear that we would start to lose track of days that started to feel the same pushed us to find something different.

One day, you might discover a secluded cove all to yourself; the next, a storm is threatening to drag your anchor away in the middle of the night. Not every day is good, but no two days are alike.

Minimalist Lifestyle

When you live in a space not much bigger than a bedroom, minimalism isn’t optional. But rather than being restrictive, it can be freeing—less clutter, fewer distractions, more time for what matters.

When we first moved aboard, we had been living in vans. Suddenly, the boat felt HUGE — a second berth, a separate dining and living area, even a desk to work from. We had more than enough space. Four years later, that sense of space has definitely faded, but the lesson has remained: enough is often a matter of perspective.

Connection with Nature

The liveaboard life pulls you into rhythm with the elements. Wake with the sunrise, watch the sky for shifting clouds, feel the wind gathering strength, and listen to the rigging hum in the breeze.

And every so often, the ordinary gives way to magic — dolphins ride your bow wave, the sunset splashes the horizon with impossible colors, a loggerhead turtle surfaces beside you while you swim, or a full moon lifts itself straight from the sea. These moments remind you why you chose this life: raw, unpredictable, and often breathtaking.

Paradise Found

Crystal-clear bays, sandy beaches, and bucket-list destinations can become your backyard. You don’t just visit — you live there, even if only for a while.

And while the novelty can sometimes fade, you only need to see sailors coming for single week of vacation to be reminded: this is your everyday. It’s a rare privilege — one worth the effort it takes to sustain.

Unique Family Experiences

For families, boat life offers something extraordinary: more time together, new cultures, and adventures most children only read about. Kids grow up adaptable, resilient, and immersed in the outdoors.

Nora’s first year has been a string of extraordinary “firsts”: wobbling her first steps across a rocking deck, splashing in crystal-clear water as she learned to swim, and charming Greek nonnas at seaside tavernas while stuffing fistfuls of tzitziki into her mouth. She may not remember the details, but I like to think some part of that experience will stick with her.

Strengthens Relationships

Living aboard as a couple means tackling everything as a team: navigation, repairs, anchoring, and weathering storms. It can test patience, but it also forges resilience and deepens trust.

From the very beginning, our relationship has been built on a shared dream of travel and the work of making that dream real. Along the way we’ve added new dreams — building a business, getting married, raising our daughter — but at the core, adventure and exploration have always been the foundation.

Affordable

While it’s not a given — and many people choose a costly version of sail life — it can be a simple and affordable way to live.

With no rent or mortgage, lower utility bills, fewer consumer temptations, and no permanent address to receive Amazon or Pizza deliveries, many liveaboards find they spend less than they did on land.

We spend far less living abored than we did on land, and it has allowed us to reinvest those savings for the future.

👉 Check out how much we spend living on a boat in Greece

Community

Despite being a transient lifestyle, the sailing community is remarkably welcoming. In harbors and anchorages, friendships form quickly, often with people from vastly different backgrounds.

These connections may not last forever, but they can be strong while they last — and you’ll likely cross paths again.

Benefits of Remote Work and Nomadism

One of the biggest perks of boat life today is the freedom to work without the limits of an office or a 9–5. Your commute is making your way up on deck, meetings can happen while underway to your next anchorage, and you can shut the laptop whenever it’s time to jump in for a swim.

You set the schedule, not the rush hour. And for many including us, working remotely accross borders can add financial upside too — from tax advantages to stronger buying power.

Sense of Adventure and Accomplishment

From mastering a tricky docking to completing a long passage, boat life offers constant challenges and rewards. Each victory feels earned, and each story is one you’ll never forget.

⚠️ Cons of the Liveaboard Lifestyle

Uncertainty and Danger

Life afloat is full of unpredictability. Unforecast storms roll in, equipment fails, and the sea doesn’t always play by the rules. Sailing carries inherent risks, and stress often comes with the territory.

Not a season has passed without moments that left us shaken and questioning whether sailing is really for us. So far, each time we’ve taken a breath, brushed it off, and come back stronger — better sailors, better prepared for the sea’s challenges. But it would be naïve to believe that will always be the case.

Sparse Lifestyle

Minimalism can feel freeing — but it also means compromises. Limited storage, tight spaces, and a lack of everyday comforts can become frustrating, especially when other issues, like hot weather, illness, or cranky kids, crop up.

Weather Dependency

Your plans live and die by the forecast. Waiting days for a safe weather window or diverting to a different port is part of the deal. For planners, that lack of control can be tough.

And even when you do show the patience to wait for a fair forecast, there’s no guarantee the weather will turn out the way it was predicted.

Paradise Maintained

Living in paradise takes work and planning. Life on a boat may look like a dream, but when things go wrong — and they always do — reality hits hard.

Salt water, constant motion, and relentless sun wear down boats and their systems almost as quickly as you can repair them. Sometimes it’s something small, like a torn liner in the cabin. Other times it’s something critical, like a failed anchor windlass. You can never predict exactly what will go next — only that something will — and maintenance never ends.

Layer on the logistics of living at sea, often in foreign countries, and the to-do list grows longer: visas, registrations, insurance, banking, spare parts. It can eat up just as much time as the sailing itself..

Unique Family Challenges

Families afloat face added layers of complexity: keeping children safe on deck, schooling at sea, and managing routines in very small spaces.

We were nervous before setting sail with Nora. Sailing alone could be stressful, and we’d already learned that parenting a baby ashore wasn’t exactly a walk in the park. What would it mean to combine the two?

Plenty of people warned us it just wouldn’t be possible. But it was — and ultimately, it was wonderful. Still, it came with its own set of challenges.

For us, it meant trying to coordinate nap schedules with passage planning, and finding creative strategies for dealing with soiled diapers between ports.

For Nora, it meant setbacks in learning to walk on a moving boat, the frustration (and indignity) of being bundled into a bright life jacket, and figuring out how to navigate her little world in the saloon.

And then there was socialising. We made efforts to connect with other sailing families with little ones, but the truth is there aren’t that many out here. Playdates were rare, and we often wished there were more kids Nora’s age to share the experience with.

Relationship Pressure

Life aboard can amplify tension. In a small space, there’s no cooling-off period when tempers flare, and even small disagreements can feel big. Stressful moments — like docking in crosswinds or dealing with a breakdown — often bring arguments, and when one person feels they’re carrying more than their share, resentment builds quickly.

Boat life tests patience, communication, and teamwork daily. The same challenges that can strengthen a relationship can also strain it to breaking point.

How to Live on a Sailboat With Your Partner: 24 Liveaboard Lessons From a Sailing Couple

Expensive

While boat life can be affordable, it can just as easily drain your bank account. Purchase price, marinas, insurance, maintenance, and surprise repairs all add up quickly — and the more comfort you want, the faster costs climb.

Everything on a boat seems to carry an unexplainable premium. A simple part or repair on land suddenly costs two or three times as much at sea.

Without ruthless budgeting and careful accounting, expenses can balloon before you know it.

👉 Use our Sail Life Budget Template to estimate what boat life would cost, and keep a careful track of your finances aboard.

Lack of Deeper Personal Connections

It’s not hard to make a few friends in anchorages, but most of those connections are fleeting, often tied to a season or a port.

Meanwhile, family and close friends back home are far away. Birthdays, weddings, and simple Sunday dinners happen without you, and over time, that absence can weigh heavily.

The sailing community is welcoming, but it can’t always replace the depth and comfort of long-term relationships — the people who’ve known you long before the boat.

Challenges of Remote Work from a Boat

Internet isn’t always reliable. Mobile data drops out when you need it most, and even Starlink isn’t infallible. Add in rolling anchorages, power limitations, and the constant need to plan around weather windows and long passages, and it’s easy to watch a workday unravel.

Working afloat is possible — many people do it — but it’s rarely a smooth experience. Deadlines compete with forecasts, video calls glitch out mid-sentence, and “office hours” often bend to the demands of the sea rather than the other way around.

Sense of Missing Out

While you’re chasing horizons, friends back home may be buying houses, raising kids with steady routines, or advancing their careers. Social feeds fill up with weddings, baby showers, and promotions — reminders of milestones you’ve chosen to step away from.

The sense of missing out is real, even when you know the path you’ve chosen is worth it. Because in place of those traditional milestones, you’re collecting different ones — a sunrise at sea, a child’s first steps on deck, or the thrill of making landfall in a new country.

⚓ Final Thoughts on the Liveaboard Lifestyle

Living aboard isn’t a perfect life — it’s a different life and in many ways a tougher life. For some, the constant maintenance, small space, and unpredictability are obvious dealbreakers. For others, the freedom, connection to nature, and sense of adventure far outweigh the challenges.

For us, the rewards have been worth it. The liveaboard lifestyle has given us unforgettable experiences, reshaped our priorities, and offered a way of living that feels more vivid and intentional.

If you’re considering it, the best advice we can give is to try it out. Charter a boat, spend a season cruising, or move aboard part-time to see if the dream matches your reality.

And if you want to dive deeper into the practical side, check out:

• How to Buy a Liveaboard Sailboat
• Costs of Owning a Sailboat: With Free Budget Template
• How to Live on Boat Simply and Affordably
• Living on a Boat in the Mediterranean: The Complete Guide