How to Bareboat Charter Like a Cruiser

Chartering in Polynesia can feel like paradise. Just don’t let the postcard views distract you from the basics, such as anchoring etiquette. Denis Ulyanov

It was shaping up to be ­another postcard-perfect day at anchor in Thailand. My husband, Jamie, was working on deck aboard our Stevens 47, Totem, when he let out a shout that made everyone’s spine snap straight.

“Hey! Hey! Look out!”

A bareboat charter catamaran was bearing down on us—fast—and the people aboard were too busy laughing and posing for selfies to notice. The skipper finally looked up from his phone just in time to veer away, clearing our anchor chain by maybe 10 feet. 

“I saw ya, mate,” he called out. 

Sure you did.

For anyone who dreams of cruising, chartering can be a brilliant first step. But the gap between dream and disaster can be alarmingly narrow. Done right, bareboating is a confidence-building adventure. Done wrong, it can be a deal-breaker.

If you’re thinking of chartering as a stepping stone to life afloat, here’s how to get it right, from the skills you’ll need to the surprises you’ll want to avoid.

Build the Right Skills 

A successful charter doesn’t just depend on your spirit of adventure. It also relies on your ability to handle the fundamentals. 

Even seasoned sailors can get tripped up when stepping aboard a vessel that’s significantly different from what they’re used to handling. Twin engines, catamaran maneuvering, electric winches, a ­heavier displacement hull—all these variables affect everything from docking to anchoring to systems management.

“If you’ve been off the water for a while, or if your experience has all been in smaller or simpler boats, consider brushing up before your trip,” says Tracy Sarich, owner of Voyage Makers Coastal Adventures in British Columbia, Canada. “One of the most common issues we see is a gap in skills that becomes clear only once a client is already at the dock. That’s hard on everyone.”

To avoid that last-minute scramble, consider taking a refresher or liveaboard course with American Sailing or the Royal Yachting Association, or through the charter base. Many companies offer training designed to mirror real-world charter conditions, often using the same types of boats you’ll be renting. Not only does this kind of refresher course sharpen your skills, but it also builds confidence and reduces anxiety for you and your crew.

“Research your charter company’s requirements early,” Sarich says. “Then plan your prep accordingly. We tailor training to match both the boat and the cruising area, so charterers feel ready when it’s time to go.”

The more solid your foundation, the more fun you’ll have—and the more likely you’ll be planning the next adventure before this one’s even over.

Be Honest 

It’s important to recognize that while your sailing skills might be top-notch in your home waters and familiar conditions, those skills might not translate seamlessly to a new charter-base location. Charter bases often vet those skills carefully—especially in areas with more-complex navigation dynamics.

Charter guests can get frustrated when required to sail with a checkout skipper. “Do they think I’m not experienced?” “Did they not believe my sailing résumé?” In reality, it’s not about mistrust—it’s about setting you up for a safe and enjoyable trip.

“Charter companies want your experience to be a positive one,” says Capt. Margaret Pommert, a veteran sailing instructor who conducts checkout orientations for charters in Puget Sound. “They know their boats and waters better than anyone, and they’ve seen what can go wrong.”

A checkout skipper’s role is to familiarize guests with the vessel and local conditions, ensuring comfort with handling, docking and onboard systems. At the end of the process, the skipper must determine whether the guest can safely manage the boat—and their crew.

Even seasoned sailors can be caught off guard by unfamiliar waters. Deepwater Puget Sound sailors might run aground in Florida’s shallows. A salty Southern California sailor might struggle when the “wind machine” kicks in on a summer afternoon in San Francisco Bay.

Pommert remembers a Chesapeake Bay sailor—and hopeful family cruiser—who was planning a Puget Sound charter with his anxious wife and young children. He ­proudly explained that he had interpreted the local tide tables and intended to sail through Deception Pass on a max ebb current. Recognizing this as a recipe for disaster, Pommert gently explained the danger of his plan and introduced the concept of a tidal gate. Together, they reworked the itinerary.

A month later, the family bought a sailboat. Six months after that, his wife enrolled in one of Pommert’s courses.

A good checkout skipper is a mentor and partner. They help you build on your strengths, identify knowledge gaps, and ensure that your charter is a success. It’s a rare ­opportunity to grow; embrace it.

Know the Systems

Even experienced sailors can find themselves flustered on a charter boat. The systems might be unfamiliar, the layout unexpected and the interface—bonjour, French chart plotter—less than intuitive. What you think of as basic sailing knowledge might not prepare you for the living ­systems that make a boat feel like a functioning home, even for a week.

On a charter, you might be managing a watermaker, monitoring battery-charge levels, or operating a macerator pump for the heads. These are things you might never touch on a daysailer or even your own coastal cruiser. Mismanaging these systems can lead to discomfort, stress and safety issues.

“In-mast furling systems, for example, are very common on charter sailboats,” says Tracy Sarich of The Voyage Makers. “Clients who say they know how to use them—because they’ve watched a YouTube video—are often the ones calling on day one when something goes wrong. These issues could be avoided if they gave themselves a little more time for discussion at the dock.”

Before you board, ask for a list of the boat’s equipment. Familiarize yourself with anything unfamiliar. Charter ­companies might be able to provide videos or manuals. If not, a little digging online—­especially on YouTube—can go a long way. Make a checklist of key systems that you want to understand: How do you monitor tank levels? Where are the breaker panels? How does the autopilot engage? And, yes, how do you flush the toilet?

Even details such as PFD comfort, dinghy operation and stove ignition can feel like small wins if you take the time to get familiar up front. The orientation provided by the charter base is valuable, but it’s not always enough, especially if you arrive rushed or distracted. A little homework before you go can make your entire week more enjoyable. 

Research and ­Prepare

Sailing in a new place can be thrilling—but also deceptive. It’s easy to assume that your sailing skills will transfer ­seamlessly. In reality, every destination has its quirks, risks and local ­knowledge. Maybe it’s the swift tidal currents and narrow passes of the San Juans, or the sharp katabatic winds that come screaming down Greek hillsides in the Med. Even the most seasoned sailors can be caught off guard when they underestimate the local conditions.

Nothing beats advanced planning and asking questions of your charter company ahead of time so that you can discuss your plan with a local expert upon arrival.

“Most accidents occur on charter boats because clients have overestimated their ability to read the conditions in a new area,” Sarich says.

She appreciates when guests take time before their trip—and during that first day of orientation with The Voyage Makers—to plan and prepare, making their vacation more relaxing. It can also save money, especially when security ­deposits are at stake.

Lara Ortiz runs Ocean Adventure Cat charters with her husband, Jason Decker, and has seen both sides of the coin when it comes to research.

“We met some nonmariners on a dive trip in Borneo who were super-interested in sharing a bareboat with us one day,” she says. “They joined us in St. Lucia, loved it, and went home to Germany to earn their sailing certifications. A year and a half later, they invited us on a sailing trip in Croatia, with Jason as the backup skipper.”

On that trip, their friend—the first-time charter skipper with an engineer’s mindset—brought along a 3-inch binder with divider tabs. It included detailed information on the cruising grounds, potential itineraries, summaries of each destination and port, anchorage and marina chart screenshots, explanations of local weather patterns, guidance on areas to avoid and how to identify risk factors, and diagrams of line and rudder configurations for different docking conditions.

Ortiz and Decker were the only experienced sailors aboard, but each day, their friend—the new skipper—would review ­relevant maneuvers with the crew and assign clear roles.

“He maintained great communication during sailing, docking and anchoring,” Ortiz says. “Preparation paid off, and the trip was a rousing success.”

Be Realistic

One of the most common causes of charter disappointment is an overstuffed itinerary. It’s tempting, especially on your first trip, to try to check off every beach, bar and snorkeling spot that you flagged in the guidebook. But cramming too many destinations into too few days almost always backfires. You spend your week rushing between anchorages, eyes on the clock, powering through squalls or skipping swims—all just to stay on schedule. 

Charter yachts convey easy living, but good seamanship still matters. Denis Ulyanov

The problem is mindset: We come from lives governed by fixed calendars and concrete deadlines, where a change in the weather just means packing an umbrella. But sailing doesn’t work like that. Weather shifts, boats need attention, and sometimes the best-laid plans give way to the perfect cove you didn’t expect to fall in love with.

Give yourself time, especially on day one. Settle in, get to know the boat, and slow your roll. Marla Hedman, a captain with The Voyage Makers, recalls a charter crew who arrived late, eager to cast off and make their first anchorage before sunset. In their haste, groceries were hurried aboard, the boat briefing was rushed, and they motored out without properly checking systems. 

Later, when they went to raise the main, the electric winch jammed—and they kept pressing the button. Pop. Pop. Pop. The halyard, still routed through the lifelines, ripped stanchions from the deck one by one. Their charter ended ­before it really began.

The lesson? Prioritize ease over ambition. Aim for fewer destinations, with more time at each. Let the weather and your mood guide your course. Savor the unplanned layover, the lingering lunch or the unexpected sunset in a bay you didn’t even mean to stop in. 

When you make room for spontaneity, that’s when magic tends to happen.

Bring Perspective

Your mindset is one of the most important pieces of charter prep—more than any checklist or chart-plotter app. 

Charter boats get used hard. Systems wear, cushions fade, things break. The air conditioning might groan in protest, the dinghy might have a sticky outboard, and the watermaker might be out of commission entirely. None of these situations is ideal, but none of them need to ruin your trip.

One of our coaching clients, fresh back from a weeklong charter in the BVI, told us: “It wasn’t exactly as advertised. Our boat was supposed to have a watermaker, but it wasn’t working. Yet for one week in the BVI, it was easy enough for us to manage on board.” 

His takeaway? A little flexibility and problem-solving made the trip feel more like an adventure and less like a resort stay. That’s actually pretty close to real cruising, where “something always needs fixing” is less a complaint than a mantra. If you treat minor hiccups as part of the story, then you’re already thinking like a cruiser.

There’s also another way to bring perspective: If you’re chartering and curious about the liveaboard lifestyle, look around the anchorage. Cruisers are easy to spot. They typically have laundry flapping from the lifelines, an array of solar panels, jerries lashed to the rail, and someone in the ­cockpit elbow-deep in an electrical panel or a winch servicing. Go say hi. Most of us remember exactly what it was like to be cruiser-curious, and we’re ­often more than happy to swap stories or offer a quick tour.

Just maybe don’t drop your anchor right on top of theirs.

Pregame Like a Cruiser 

If you’re treating your charter as a trial run for future cruising life, don’t wait until you’re aboard to start thinking like a full-time ­sailor. Use the planning phase to build real-world skills and gain confidence with the tools that cruisers rely on daily. Try this ­four-step checklist before you even book your flight.

Practice With Charting Software: Install a navigation app such as Navionics or Aqua Map on a tablet. Practice route planning manually to get familiar with chart overlays, depth contours, and hazard markers. No auto-routing.

Track Weather: Download a robust marine forecasting app such as PredictWind. Ask your charter base which forecast models they trust most for the local area, then begin following them days or weeks in advance. You’ll get a sense of how patterns evolve in your  destination.

Scout Anchorages With Cruiser Intel: Platforms such as Noforeignland let you explore anchorage reviews and track real cruisers’ movements. Study the footprints of others to get a sense of practical, comfortable routes, as well as ones to avoid.

Understand Local Phenomena: GRIB files don’t tell the full story. Learn about region-specific weather quirks such as katabatic winds in the Med, chubascos in the Sea of Cortez, and squalls that funnel between islands. Knowing what’s likely to catch you off guard helps you stay ahead of the curve.

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