Choosing the Right Cruising Sailboat: How We Picked Ours (and What We’d Do Differently)

Thinking about buying a cruising sailboat? Here’s how we chose ours—what really mattered, what didn’t, and what we’d do differently so you can make the right choice for your adventures.

Why choosing the right cruising sailboat matters

This isn’t just a boat. It’s your adventure mobile, your home, and your ticket across oceans. The process can feel overwhelming. There are endless listings, so many opinions, and big decisions about what really matters.

If you’re shopping for your first cruising sailboat, you’ll quickly learn that every boat is a compromise. The trick is figuring out which ones you can live with, and which comprimises are non-starters.

When we first started dreaming of full-time cruising, we thought a catamaran might be possible. And it would have been if we had the patience to save longer. But we aren’t patient people by nature. Instead, we dialed in the budget and focused on finding a safe, reliable monohull that could take us anywhere. Honestly, I just wanted a boat whose keel wouln’t fall off in the middle of the ocean.

That decision led us to Raicilla, our 1979 FastPassage 39. She’s solid, forgiving, and a capable cruising sailboat. Here’s how we chose our sailboat for full-time cruising: what we thought mattered, what actually mattered, and what we’d do differently if we were buying again.

What to look for in a cruising sailboat (and what we chose)

Like many new cruisers, who watched too much YouTube,  our plan was ambitious. Circumnavigate the globe. That shaped our priorities from day one. We wanted a boat that could:

• Handle a variety of conditions safely.

• Be manageable for two people (or one) to sail.

• Feel comfortable enough to live on full-time.

In practical terms, that meant looking for:

• A strong hull design (no bolt-on keels, skeg-hung rudders).

• A cockpit with high sides, or ideally a center cockpit.

• A size around 40 feet.

Originally, we told ourselves we’d save for five years before buying so that we’d have enough money saved for a boat and a solid cruising budget. That plan didn’t last long (see the patience thing above). With the help of a broker we’d met early on, we shifted gears, set a loose budget of around $100,000, and started looking seriously. Our hope was to spend less. But as anyone boat shopping knows, budgets are just a number.

If you’re starting the buying process, write down your non-negotiables (like hull type, cockpit style, or length). These will keep you in check when the “shiny” listings pop up.

Yachtworld.com can get overwhelming with all the choices.

What we thought was important (and what actually wasn’t)

Electric winches? Yes please! Glossy wood interiors? Oh Yeah! Fancy electronics? Must have!

And just like that, we were looking at boats that were bigger, fancier, and way out of our budget. This is when our broker stepped in. He kept us focused on the priorities: safety, comfort, and manageable size.

Early on we learned that a sailboat still sails even without electric winches, a watermaker, lithium batteries, or the latest chartplotter. And that gorgeous glossy interior means a lot of upkeep.

Once we refocused, the search got simpler. What mattered was a sound hull, updated systems, and a size we could realistically handle. What didn’t matter as much? Whether the cushions matched or if the boat looked like a yacht magazine spread.

Don’t get distracted by “toys” or finishes. Those can always be upgraded later. Focus on major systems: rigging, engine condition, deck hardware, and hull.

How we narrowed down our choices

We leaned heavily on our broker, who was a former cruiser himself. While we browsed listings online, we always sent them to him for a second opinion.

Over several months, we looked at about 10 boats in person, including two of the same model but from different years. Having no offshore experience ourselves, we relied on research, gut instinct, and our broker’s advice.

We didn’t use fancy spreadsheets or a point system. We went with feel. Some boats just felt right; others didn’t.

In the end, we stayed within budget and found a boat that was slightly under our target price, meeting the criteria that mattered most. We did a proper survey and sea trial—though the sea trial was a calm motor run with no wind. Still, it gave us a chance to get comfortable at the helm before closing the deal.

A good broker, who understands your wants and needs, is key and it’s s a great idea to invest in a professional survey. Even if the boat feels “perfect,” the survey can uncover hidden problems that affect safety and cost thousands later.

Going in the water for the sea trail after the survey

The sailboat we chose (and why)

Two boats stood out during our search: both FastPassage 39s. One had a timeless, classic look but needed a lot of updating—and came with a higher price tag. The other had a quirky, owner-finished interior that, frankly, wasn’t much to look at. But beneath the dated woodwork, it had everything that truly mattered, a new rig, engine and updated wiring and batteries. She also had some added bonuses in new electronics and a watermaker.

Our broker encouraged us to look past the ugly duckling interior and focus on the bones. That advice paid off.

The ugly interior.

We chose the 1979 FastPassage 39 with the quirky interior. She wasn’t pretty, but she was as close to a turnkey boat as we were going to find in our price range. Thanks to a few minor items flagged in the survey, we even negotiated her down further. The final price coming in under budget.

She was, in every sense, a turn-key cruising boat. The day we finally motored her out of the slip (with a lot of help), we knew we had a boat that could take us anywhere.

The first day we owned her.

What we’d do differently if we bought again

Four years later, with thousands of miles under our keel, we’ve learned a lot about what we’d change if we did it again.

We have a lot of things. Surfboards, paddleboards, spearfishing and snorkeling gear. These all need a home and a lot of times, our spare berth is covered in our things - not open for guests or even sleeping. Cynics will say get rid of the things, but more space would be something we’d prioritize if we did it again. Probably something closer to 45 or 50 feet.

We work onboard. In the 1970s, boats weren’t designed with that in mind. This means we’re huddled on the settees or in the cockpit. Again, we’d probably look at this closer next time.

And let’s face it, modern boats are wider and designed for living. A more modern boat with a roomier interior is appealing. And we tend to spend more time at anchor than sailing anyways. With modern forecasting, having a less “bluewater” and more “liveable” boat wouldn’t be bad.

We’d also change up our sail package. We bought new sails, but blindly assumed we’d use the spinnaker all the time. The reality is that it’s a bit of a pain to use. Had we chosen something on a furler - like a code zero- we’d probably get more use out of it.

If we could start over, we might have saved longer and bought a slightly newer, more spacious design. But here’s the key point. We don’t regret our choice. This boat got us out here, and we’ve never once felt unsafe aboard.

After several thousand miles and a small refit, she’s still going strong.

Final takeaways: tips for anyone choosing a cruising sailboat

Here’s the truth: there is no perfect sailboat. Every boat is a compromise.

What matters most is finding the balance that works for you. For us, that meant prioritizing seaworthiness and reliability over beauty and shiny gear. Your priorities may be different. Knowing them before you start shopping will save you in the end.

A few final tips for choosing the right cruising sailboat:

• Focus on safety and construction. A beautiful boat isn’t worth much if it can’t handle your sailing plans.

• Don’t get distracted by add-ons. Those can be added later.

• Set a realistic budget and a budget for add-ons. There will always be surprises after purchase.

• Trust your gut. A boat that feels wrong probably is.

• Don’t wait forever for the “dream boat.” The best cruising sailboat is the one that gets you sailing, not the one sitting in your bookmarks.

It’s less about finding the perfect boat and more about finding the boat that gets you out on the water and living the life you’ve been dreaming about.