Is Cruising Realistic for My Situation?

You’ve caught the bug. You’ve read the blogs, watched the videos, maybe even spent a few nights aboard. And now you’re asking the harder questions. Not “what is the cruising life?” but “can I actually do this?”

The questions below are the ones we hear most often from people who are seriously considering cruising but haven’t yet convinced themselves it’s possible for their specific situation. We’ll give you honest answers. Not cheerleading, not scare tactics. Just what our team knows from decades of living it and talking with thousands of cruisers who wondered the same things.

Can I afford it?

How much it costs to cruise on your own boat is one of the most frequent pre-cruising questions people have. And rightly so. There are two parts to the cost question: the initial cost to buy a boat, and the ongoing monthly cost of cruising.

The boat

A decent, older monohull that is genuinely ready to cruise typically costs $50,000 to $100,000. Factor in another $10,000 to $30,000 to bring the systems up to where you would want them. Catamarans start higher, usually $100,000 and up for anything reasonably equipped. Other costs to add:

A survey before purchase
Initial outfitting before you leave the dock
Sales tax and registration
Boat insurance from day one

The boat purchase is a one-time cost, but it is never just the number on the listing.

Monthly costs

I know people who cruise on $1,500 a month and others who average $10,000 or more. The bottom line is that it is possible to cruise on just about any budget. The question, really, is whether you will enjoy cruising on that budget. In general, lower budgets mean:

A smaller, older boat (probably not a catamaran)
Fewer meals out or marina stays
Fewer side trips
Planning your route with an eye to costs

One of the biggest mistakes I see people make is trying to cruise on a budget that simply does not reflect their own preferences. Just because you read a blog where someone says they live on less than a thousand dollars a month does not mean it is right for you.

Additionally, when you look at cruisers with seemingly low expenses, look to see if they leave some things out of their report. Many do not include alcohol, health insurance, or even some boat expenses.

Then look at what low-budget cruisers are actually doing every day in order to live on that budget:

Rowing the dinghy so they do not use gas
Catching fish for dinner or going without
Using 10-year-old charts
Living without refrigeration
Going engineless until they can afford the parts to repair it

Many things sound romantic to read about but are not when you are the one living the life.

A budget of at least $4,000 a month (assuming the boat is paid for and in good shape) is probably more realistic for a couple as a starting point.

Then add:

Health insurance. This varies so much from person to person that it is hard to give a number. It can range from near-zero if you have great retirement coverage or a highly subsidized plan, to over $2,500 a month per person on a pre-Medicare individual policy with no subsidy.
Loan payments, if you financed the boat
Planned upgrades
An emergency fund for unexpected repairs or a serious health issue

Can I work while cruising?

If you want or need to earn to make your cruising budget work, the good news is that it is very possible. The huge rise in remote work since 2020, combined with Starlink internet covering the globe, has opened up opportunities that simply did not exist a few years ago.

In addition to remote work, other options include:

Staying in one location for three to six months for a temporary job such as travel nurse, dive instructor, bartender, or waitstaff
Boat maintenance and repair work for other cruisers, if you are handy
Delivery captain or crew
Returning home to help out at a former employer during a busy season, such as tax preparation
YouTube, photography, magazine articles, and similar creative work

One important note: working in a foreign country almost always requires a work permit, and failing to get one can result in deportation. Online work has far fewer restrictions, which is one more reason it has become the most common option.

Am I too old?

Age, in itself, is not a barrier to cruising. Dave and I began cruising when he was 64 and actively cruised until he was 83. We continued to live aboard until he was 85. And he was not the only one. In 17 years of cruising, we met a few people still out there in their 90s.

Cruising helps keep you young. There is more physical activity than living ashore, and it requires more of you mentally too. Figuring routes, solving problems, navigating new places and cultures.

Cruising in your 50s or 60s may not take much adaptation at all. Cruising in your 70s or 80s likely will. Most people find they make adjustments like these:

Budgeting more for help with heavy work
Rigging the boat to make things easier (a watermaker, extra purchase on the dinghy davits, electric windlass)
Watching the weather more carefully and staying put when it is iffy
Planning shorter hops with fewer overnight or multi-day passages

None of that diminishes the experience. It just means cruising on your terms.

When we began cruising in 2002, almost all cruisers were retired. It has only been as remote work has opened up that more young people are getting into it for longer than a sabbatical year or two. Starting later has real advantages: more financial stability, more patience, and a clearer sense of what you actually want from the experience.

If you are older and not yet familiar with what living aboard involves, I recommend my course The Basics of Living on a Boat. While many skills may be new, I think you will be reassured that they are manageable.

Further reading:

Cruising When Older

Could I cruise with a health condition?

Most medical conditions can be accommodated. Over the years I have met:

Cruising sailors with heart conditions and cancer
Two amputees who cruise solo
A cruising couple in Mexico who were both legally blind
A cruising family with two of seven children in wheelchairs

I am diabetic. CPAP machines can be run aboard. Most things can be accommodated.

How people make it work varies:

Extra equipment, such as carrying an AED for someone with cardiac problems
Planning a route that puts you within reach of medical treatment at regular intervals
Recognizing that certain conditions put you at extra risk in remote areas and deciding either to avoid those areas or to accept the risk with open eyes

With Dave cruising at 83 with a variety of known health problems, we did a combination of both. We went to the Bahamas but stayed mostly in areas where help and quick transport to US hospitals was available. Before the trip, we talked through the risks. Dave’s take was to quote Jimmy Buffett: “I’d rather die while I’m living.”

What about medications?

Many chronic conditions require maintenance medications. Cruisers manage with a combination of:

Mail-order pharmacies shipping to marinas
National chain pharmacies where it is easy to transfer a prescription
Local doctors and pharmacies in foreign countries

It takes planning ahead and a willingness to factor your medication schedule into your route. You may not always get your insurance to pay. But for most medications, it can be done.

If you want to make it happen, there are ways. Wanting is the key. It is not always easy, so your desire to make it work has to be genuine.

Further reading:

Do people cruise with kids?

Every year we see more and more “kid boats” with the rise in younger cruisers, and the kids are thriving. They tend to be:

Mature beyond their years
Able to see the real-world applications of what they are learning
Comfortable making friends across cultures and often across languages

As homeschooling has become more accepted generally, and especially since the pandemic, boat-schooled kids find very few barriers to college or future careers. Many have a much clearer sense of what they want to do than their land-based peers.

Further reading:

Cruising with Kids

Two great books, both by cruisers:

Voyaging with Kids (Amazon)
Homeschool Teacher (Amazon)

Could we take our dog or cat?

Absolutely. Many boats have pets aboard, and they seem to love the life. Just as on land, pets will influence what you do and how you do it. But they can also make the experience much richer.

We adopted our dog Paz in our second year of cruising and she spent 10 years aboard with us. I can give more detail on dogs than cats, but many of the same considerations apply to any animal:

Dogs on Boats: What You Need to Know

For the full picture on training, health care, safety, and international entry requirements, our course Boating With Your Dog covers it all.

Can I get internet on the boat?

The internet situation keeps getting better and cheaper. For coastal cruising, your phone as a hotspot works in most locations. In more remote areas, Starlink is a total game-changer. It works even in the middle of the ocean.

A few practical points:

Do not count on marina WiFi for anything beyond an occasional weather check. A shared connection tends to be slow and there are real privacy concerns.
Budget for your own connection rather than relying on whatever is available.
Improved battery technology and lower-cost solar panels have made powering a connection and your devices aboard much more manageable than it was even five years ago.

What do I do with my house and all my stuff?

There is no one-size-fits-all answer. If you are part-year cruising, it may not even be an issue.

For a sabbatical or open-ended cruise, start with this question: would you want to return to your current location when it is over?

If yes: renting the house or using a housesitter keeps your options open
If not necessarily: selling or giving up the lease and putting what matters in storage makes sense

One strong recommendation regardless of which direction you are leaning: keep your current home for at least the first six months of cruising. Knowing you have not made an irrevocable commitment takes real pressure off the early days. Counterintuitively, that makes a successful, lasting cruise more likely, especially if one of you is still uncertain.

Further reading:

I’m interested, but my partner isn’t. Are there ways it can work out?

This is a big issue for many couples, but there are real ways to work through it. The first step is finding out exactly why your partner is reluctant. Only by understanding that can you look for compromises and solutions.

Our course The Uncertain Cruiser is designed for exactly this situation. It has two tracks: one for the uncertain partner and one for the enthusiastic one, helping both of you work toward a shared understanding, or honestly decide together whether cruising is really the answer.

My family thinks I’m crazy.

You are not crazy at all. There are thousands of people out cruising right now, and most of them heard the same thing from their families before they left.

Some families come around quickly once they see that you have thought it through. Others take longer. The key, as with a reluctant partner, is communication. Until you know exactly what they are afraid of, you cannot address those fears. But if you have gotten this far, you have probably already considered most of what they will raise, and you will have real answers for them.

Further reading:

When Family Doesn’t Want You to Cruise

I don’t drink alcohol. Will that be a problem socially?

While cruising has a bit of an alcohol-infused reputation, the reality on the water is very live-and-let-live. Almost all cruiser gatherings are bring-your-own-drink, so you simply bring whatever you enjoy. Someone may offer you an alcoholic drink, but a simple “no thanks” is all it takes. Nobody tracks what is in your cup.

If you prefer that people not bring alcohol aboard your boat, or you would rather not socialize in settings where others are drinking, you may find things slightly more limited. But plenty of cruisers navigate that just fine too.

What are my next steps?

If you have read this far and you are still thinking “yes, I want to do this,” that matters. Here is where to put your energy.

Charter before you buy. A charter vacation is one of the best ways to find out whether the cruising life is really for you. If you hate a charter, you will almost certainly hate having your own boat. If you love it, that tells you something important too.

Yes, a charter is a vacation. Someone else handles the maintenance, and the boat arrives in working order. If it is a crewed charter, even more is handled for you. But you will still see what goes into running a boat from day to day, and you can use that time to imagine: what if this were my boat and my responsibility? Who fixes things when they break? Who provisions, cooks, and cleans up? Who handles the anchor, the lines, the weather calls?

A charter is not cheap. But it is a lot cheaper than buying a boat and discovering the life is not for you.

Learn to sail and navigate. ASA and US Sailing both offer structured courses, and many local sailing clubs offer affordable instruction on the water. Take a course, then practice what you learned before taking the next one. Your insurance will likely require certain certifications, but the certificate is not the goal. The goal is being able to actually handle a boat.

Resist the temptation to stack all your certifications into a single compressed week. You will have the paperwork but not the real competence. Space your learning out, get genuine hours at the helm between courses, and the skills will stick.

Build the infrastructure for earning while cruising. If you will need income while out there, the time to lay the groundwork is before you go. You are not trying to already be earning remotely right now. You are building the conditions that will make it possible:

Cultivating relationships with potential clients or employers
Developing skills that translate to portable or freelance work
Transitioning into a role that can be done from anywhere
Starting a side project that could grow into a real income stream

Remote work income does not appear overnight. A year or two of groundwork makes an enormous difference.

Understand the insurance picture before you buy a boat. This is the step most people leave until too late. Boat insurance for liveaboard cruisers has gotten harder to find and more expensive. Many insurers will not cover:

Boats under a certain value (often $75,000)
Boats over a certain age
Cruising grounds outside specific geographic limits
Owners without a documented sailing resume showing adequate experience

The sailing resume requirement is what catches people off guard. Insurers want to see experience on boats comparable in size and type to the one you want to insure. Time on a 20-foot daysailer will not satisfy an insurer for a 42-foot offshore cruiser. If you have your eye on a catamaran, you will need catamaran hours specifically. Many insurers also want to see overnight and offshore passages, not just coastal day sails.

The practical implication: have a rough idea of what boat you want before you start building your experience base, because the experience needs to match the boat. Start keeping a sailing log now. When it comes time to apply for insurance, you will need to document what you have done, where, on what size and type of boat, and in what role.

Research insurance requirements before you choose a boat, before you decide which certifications to pursue, and before you plan what experience to accumulate. Let the requirements shape your preparation, not the other way around.

Health insurance is the other piece to sort out early, especially if you are pre-Medicare. What you find will affect your budget and possibly your timeline.

Ready to make a real plan?

If you are ready to move from “could I do this?” to “here is exactly how I am going to do it,” we suggest starting with our course From Dreamer to Cruiser. It walks you through the real planning process step by step:

Defining what you want from cruising
Understanding the true costs
Building skills in the right order
Creating a realistic timeline for leaving the dock

It is the course we wish had existed when we were getting ready to go.

Do you have other questions we could help you with?

What Is Cruising? The real picture Could I Cruise? Budget, health, age, family Getting Ready How to make it happen First-Year Reality Help for tough times