Getting Ready to Go Cruising

Getting ready to go cruising involves more than buying a boat and pointing it south. Our team has made the move from land life to living aboard more than 15 times, and we cover it all here: buying the right boat, getting insured, leaving land life behind, handling the administrative tasks, building your skills, getting the boat ready to go, and (ta-da!) transitioning to boat life.

Buying the Boat

One of the first questions most people wrestle with is whether to choose a monohull or a catamaran. There’s no universally right answer. Catamarans have more living space, usually have less draft, and don’t heel. Monohulls generally have an easier motion on open water, fit into smaller slips, and are less sensitive to weight. They’re also less expensive than cats for the same length.

The choice comes down to your budget, your priorities, and where you want to cruise.

One thing worth thinking about before you fall in love with any particular boat is what gear is absolutely essential to you. The more systems you have aboard, the more there is to break and maintain. The happiest cruisers tend to have moderately simple boats, not floating versions of their houses, but also not totally spartan. The less handy you are, the simpler you should keep your boat, especially on a tight budget.

One thing to approach with real caution is the cheap fixer-upper that looks like such a deal. A project boat as a first cruising boat almost always costs far more than expected in both time and money. You want to spend your time cruising, not rebuilding.

The purchase price is just the starting point. A realistic boat budget includes the survey, haul and bottom paint before you leave, insurance from day one, slip fees for the early days, and initial upgrades to get the boat where you want it. Add a spares inventory on top of that, plus first-year operating costs. Most people who blow their budget in the first year didn’t overpay for the boat. They just didn’t account for everything that comes after.

If you want to understand how all your decisions affect the total cost, our course Cruise Farther, Spend Less lays out exactly how choices drive expenses.

A boat survey is the boating equivalent of a pre-purchase home inspection. A good surveyor can identify gear that doesn’t work as well as safety problems. Your insurance company will want a copy, and so will your lender if you’re borrowing. It’s not unusual for a survey to come back with a few problems, large or small. You can use them to negotiate repairs or the purchase price, or decide to walk away entirely.

Even if a survey isn’t a requirement, get one anyway. A good surveyor is the only person in the entire transaction working solely for you. The brokers get paid when the sale goes through. The seller obviously wants the sale to go through. The surveyor gets paid (by you) whether the sale goes through or not, so they have no stake in making it happen.

When the survey is done and the sale is complete, there’s a checklist of legally required documents and safety equipment you’ll need to have aboard.

Getting Insured

Insurance needs to happen in parallel with the boat search, not after. The boat you choose, the experience you’ve documented, and the upgrades you make all affect whether you can get coverage and what it will cost.

Boat insurance for liveaboard cruisers has gotten harder to find and more expensive in recent years. Many insurers have pulled back from the marine market entirely. Those that remain often have strict requirements around boat value, cruising range, and the owner’s documented experience.

I’ve talked with people who had their heart set on a boat they couldn’t insure, or who couldn’t get coverage at all because they hadn’t built the right kind of experience. Understanding the landscape before you commit to a boat can save you from both of those situations.

The requirement that catches most people off guard is the experience resume. Insurers want documented experience on boats comparable in size and type to what you want to insure. That means powerboat hours for a trawler, catamaran hours for a cruising cat, offshore passages for a bluewater sailboat. Time on a 22-foot daysailer won’t satisfy an insurer for a 42-foot offshore cruiser.

Start keeping a boating log now. Date, location, distance, boat type, your role, conditions. You’ll need exactly that information when you apply.

Downsizing and Leaving Land Life

If you’re keeping your home base, most of this section won’t apply to you. If you’re leaving land life behind to cruise indefinitely, read on.

Getting rid of a houseful of stuff is real work. Most people underestimate how long it takes and how many decisions it involves. The practical side is manageable if you approach it systematically.

The emotional side is something different, and it surprises almost everyone. Even when you’re genuinely excited about where you’re headed, leaving land life behind brings feelings you didn’t expect. Saying goodbye to friends you’ve known for decades. Selling the boat you raced every summer. Letting go of a house you poured years of work into.

These feelings don’t mean you’re making the wrong choice. They mean you had a full life ashore, and that’s a good thing.

More on downsizing and leaving land life:

Practical Logistics

Nobody talks about this part at cocktail parties, but it’s where a lot of people get stuck. There’s a cluster of administrative tasks that need to happen before you leave the dock, and most of them take longer than you’d expect.

Legal residency and mail. If you’re leaving a fixed address, you need a physical address for your driver’s license, voting, vehicle registration, and mail that can’t go fully digital. Mail forwarding services exist specifically for cruisers and handle this well. Even if you’re keeping your home, mail management is worth thinking through before you leave.

Boat documentation. You have a choice between federal documentation and state titling for your boat. State registration is also required in almost every case, regardless of which you choose. Your dinghy can’t be federally documented and usually needs a state title and registration. Learn the differences and what applies to your situation before you buy.

FCC Ship Station License and MMSI number. If you plan to cruise internationally, you’ll need an FCC Ship Station License for your VHF radio. It’s required by law in foreign waters. Your MMSI number is separate and enables AIS and DSC on your VHF radio. If you’ll be cruising internationally, be sure to get an FCC-issued MMSI number, not one from BoatUS. Neither the Ship Station License nor the MMSI number is hard to get, but both involve FCC paperwork that takes time to process.

Organizing it all. Once you start bringing gear aboard, you’ll quickly have a pile of owners manuals, registration papers, and warranty cards. Keep it organized!

Building Your Skills

Running alongside all the practical preparation is the work of becoming a confident, capable boater. Nothing prepares you more than actual time on the water.

Classes give you frameworks. Real judgment comes from real situations. The instincts you need for a building squall, an engine failure under sail, or a quick course change don’t develop from reading about them.

I know cruisers who took every certification course available and still felt completely unprepared their first month out. I also know others with minimal formal training who had spent years actually on the water and handled everything that came at them. Get out there as much as you possibly can before you leave.

While you’re building water time, there are skills you can develop onshore too. DIY repairs, spacing out grocery trips, cooking from scratch, conserving water and power. These sound mundane, but making them habits before you leave flattens the first-year learning curve considerably.

When it comes to your specific boat, use every resource available. Start with the survey. Ask yard professionals questions while they’re working on your boat. Find your boat’s owner group online. Take a diesel course, even if you’re the less mechanical partner in a cruising couple. The more you know before you leave, the fewer surprises you’ll have underway.

Getting the Boat Ready

While you’re building skills, you also need to be preparing your boat. The list never fully ends, and at some point you have to decide it’s ready enough. But some things genuinely need to happen before you go.

Your survey likely returned at least a few repair or maintenance items, and those are your priorities. At least one will likely require a haul-out. That’s your chance to do below-waterline work and tackle any other projects that need to happen out of the water.

Plan what you’ll do before you get there. Get parts in advance. Count on discovering at least one thing you didn’t expect.

Get your safety gear aboard, checked, and stored where you can actually reach it under stress. Know how to use a float plan and make it a habit from the start.

Think through spares carefully. Work through the most likely failures for each critical system and carry what you’d need to fix them. Spares are one of the most common budget surprises for first-year cruisers. You’re not just buying things you need right now. You’re buying the ability to fix problems when there’s no chandlery nearby.

Before you leave, go through every system on the boat deliberately. Nothing should be a mystery when you’re depending on it.

Transitioning to Boat Life

Here’s what nobody tells you: you will never feel completely ready. There will always be one more thing on the list, one more system to sort out, one more skill that hasn’t fully clicked. Every cruiser who has ever moved aboard felt exactly this way. The ones who went anyway are the ones who ended up cruising.

The transition goes better when you take it in stages. Start by living aboard at the marina and learning the systems without the pressure of being underway. Then anchor out nearby and get comfortable managing power, water, and the dinghy. Then day trips. Each step builds your confidence and your boating log at the same time.

Make sure both partners feel genuinely capable at each stage before moving to the next. Two people who each understand the boat are a cruising team. One skipper and one passenger is a setup for stress.

What Are Your Next Steps?

You’re close. Here’s where to put your energy.

Learn the day-to-day reality of living aboard. There’s a lot to absorb in the first months: boat systems, anchoring, provisioning, marina and anchorage etiquette, safety aboard, and the unexpected situations that come up when you’re actually out there. My course The Basics of Living on a Boat covers all of it across 31 topics. It’s what I wish I’d known before moving aboard.

Get confident on the VHF before you go. The radio is something you’ll use every single day, and the time to learn it is before you need it, not while you’re trying to raise a marina at dusk in an unfamiliar anchorage. Our course VHF Radios: Everything You Need to Know by John Herlig covers routine calls, channel selection, DSC, AIS, and emergency communications.

Get the boat organized. Moving aboard means fitting your life into a fraction of the space you had ashore. Storage Solutions for Life Aboard will help you set up the boat so everything has a place and you can find it when you need it, including when you’re heeled over looking for a tool at 2 AM.

Or get everything at once. The All-Access Pass gives you all of our courses, plus all future ones, at a significant discount off buying them individually. If you’ve already purchased one of our courses, you’ll receive an upgrade offer by email and what you paid counts toward the All-Access price. Start with the course most relevant to where you are right now, and the rest will be there when you need it — you’ll have lifetime access.

Do you have other questions we could help you with?

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