ARE YOU READY TO CHARTER A SAILBOAT? (SELF ASSESSMENT CHECKLIST)

SELF ASSESSMENT SAILING CHECKLIST

Building toward your first bareboat charter requires that you recognize a critical distinction: certification is not necessarily the same as being “ready to book.” Charter companies assess both, and understanding their perspective before you submit a résumé saves you significant stress later.

This sailing checklist breaks down the primary factors charter companies evaluate, including certification, vessel-type experience, skipper time, recency, destination requirements, and crew qualifications. Assess these points honestly against the specific vessel and destination you have in mind; requirements shift significantly between a 38-foot monohull in familiar waters and a 48-foot catamaran in a new sailing ground.

Certification

• I hold a certification appropriate to the boat I want to charter (ASA 104 for a monohull; ASA 104 and ASA 114 for a catamaran).
• My certification covers a vessel size reasonably (within ~5’-8’) close to the one I’m requesting.
• I confirmed all destination-specific requirements beyond my home certification (such as an ICC, IPC, or VHF operator’s license) and ensured I have that printed documentation in hand.

A certification is the baseline a charter company expects to see. It’s rarely the only thing they look at, which is exactly why the rest of this sailing checklist matters.

Vessel-Type & Size Experience

• I have documented time on a boat similar in size to the one I want to charter — not just the boat I trained on, if the two are different.
• For catamaran charters, ensure my recent experience includes specific time at the helm of a catamaran, rather than relying solely on monohull time.
• I can point to specifics if asked — boat model, approximate size, location, and conditions — rather than a general sense of “I’ve sailed a fair amount.”

A certification tells a charter company what you were tested on. This section is about what you’ve actually done since.

Skipper Time, Not Just Crew Time

• A meaningful portion of my logged hours were as skipper rather than as crew following someone else’s direction. This shows that I’ve had to use both my skills and judgement in real-world situations.
• I’ve handled docking, anchoring, and passage planning myself, not just assisted with them.
• If my background is primarily crew-based, I’ve mapped out a clear path to gain skipper-specific hours—such as a flotilla, a training course, or a ‘checkout’ charter with a pro aboard—before heading out on my own.

First on the sailing checklist, is skipper time. Miles logged as crew build real familiarity with a boat. They don’t demonstrate the same thing as miles logged making the decisions yourself, and charter companies generally know the difference.

Recency

• I’ve been sailing within the last year or so, not primarily relying on experience from several years ago.
• If I have taken a break from sailing for a while, I’ve prioritized getting back on the water—via local clubs, delivery trips, or refresher days—well before the charter dates.

Next on the sailing checklist, is recency. Skills built years ago don’t disappear, but a charter company has no way to verify they’re current without some recent activity to point to.

Destination Requirements

• I’ve checked what this specific region requires, beyond the charter company’s own criteria: local licensing, safety equipment rules, or navigation restrictions as these may vary by destination.
• I have any required documentation printed and ready, not just saved on a phone.

Next on the sailing checklist, you must meet the requirements of your destination(s). Requirements here are set by local authorities, not by the ASA or by the charter company, so they’re worth confirming directly with the charter operator or the destination’s maritime authority rather than assuming your home certification covers everything.

Crew & First Mate Readiness

• My first mate or primary crew member has sailing experience appropriate to the trip, not just enthusiasm.
• I know that in the event of an emergency, at least one other person aboard is capable of handling the boat and ensuring the crew’s safety.

Finally on the sailing checklist, your crew must be ready. Charter companies rarely hand a boat to a solo-capable skipper with an unqualified crew, for the same reason this matters to you and your crew directly: a boat is safer when responsibility isn’t resting on one person alone.  Insider tip: conduct important drills with your crew immediately after you leave the dock!  Make sure that your team knows how to conduct an MOB recovery, raise and lower sails, turn engines on and off, and make basic maneuverability turns.

Reading Your Results

Checking most of the boxes on this sailing checklist puts you in a strong position to charter. This is the time to begin a conversation with your broker or charter company.  Discovering a few honest gaps is perfectly normal; it simply points to specific, fixable next steps, such as building more time as skipper or starting with a more familiar boat.

Working through this honestly now is a far better position to be in than finding out about a gap on the dock, on the day you were hoping to leave.

Next Step

Not sure how to read your results, or want to build your resume with a sailing course? Get in touch and we’ll be happy to talk through it with you — no obligation, just a conversation about where you are and what a reasonable next step looks like.

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Related reading:

• What You Can Actually Do After ASA 104 & 114
• How Long Does It Take to Learn to Sail?
• What Most Beginners Get Wrong About Learning to Sail
• ASA vs RYA, Which Sailing Certification is Right for You?