A long sail—whether it’s an overnight passage, a multi-day crossing, or simply pushing beyond your usual comfort zone—demands more than a glance around the deck.

We are getting ready to sail across the Mona Passage from the Dominican Republic to Puerto Rico, and we wanted to share what we are inspecting before sailing for 2 days non-stop. This pre-departure inspection isn’t about perfection. It’s about reducing risk, catching problems early, and giving yourself options when conditions change

Rigging and Sails: Your Primary Engine

Start with the rig, because once you’re underway, this is not an easy system to fix. Finding a small crack in our backstay led to a major re-rigging just days before we were about to set sail for the Bahamas in 2023. We were so glad to catch it early since we personally know cruisers who have lost their whole mast due to rig failure.

Inspect standing rigging carefully. Look for rust stains (anything that isn’t just surface rust), cracked swages, broken wire strands, or bent turnbuckles. Any discoloration near terminals can indicate internal corrosion. Keep an eye out for rust that is pitted deep into the metal. 

Running rigging deserves hands-on attention. Make sure reefing lines are rigged correctly and can be deployed without re-leading lines in rough weather.

Check sails in high-load areas: head, tack, clew, batten pockets, and reef points. We tend to do a big inspection of sails when we take them down or just before hoisting them back up. Loose stitching or small tears can become major failures offshore.

Deck Hardware and Safety Systems

Deck gear takes constant load and constant abuse. Spin each winch to ensure it freewheels smoothly and engages properly. Listen for grinding or binding. Check cleats, blocks, tracks, and travelers for cracks, loose fasteners, or backing plates that flex under load.

Inspect lifelines and stanchions by pushing—not just looking. Any movement means something below deck needs attention. If you use jacklines, inspect them for UV damage and confirm attachment points are solid and positioned to keep the crew on deck, not dragged alongside. With two little ones, our netting is a major priority to keep them onboard and it has also saved our generator from falling overboard during a sail. Make sure everything on deck is secured safely and lifelines are hooked.

Engine and Mechanical Systems

Even if you plan to sail the entire way, the engine is your emergency lifeline. We have made do without an engine and sailed for nearly half a year around the Bahamas and US, but having an engine does remove a lot of stress and allows you to maneuver more easily in tight areas.

Check engine oil level and color. Milky oil or strong fuel smells deserve immediate attention. Inspect belts for cracks and proper tension. Open and clean the raw water strainer, then start the engine and confirm a strong water flow at the exhaust.

Run the engine long enough to ensure it reaches operating temperature as well as shifts easily into forward and reverse.

Electrical and Navigation Systems

Before a long sail, turn on navigation electronics: chart plotter, depth, wind, AIS, and autopilot.

Test navigation lights in shade or darkness—daylight checks can be misleading. Test your VHF radio operation and confirm your microphone and speaker are working.

Most importantly, ensure you have backups: a handheld GPS or phone nav app (we like navionics or aqua maps, depending on location), and a handheld radio because if your mast comes down or you are struck by lightning, your main VHF is useless.

Plumbing, Through-Hulls, and Bilge

Inspect all through-hulls and seacocks. Operate each one—if it’s frozen, stiff, or leaking, address it. Confirm hoses are double-clamped where appropriate and not cracked or brittle. We tend to close the intake water thru-hulls for our heads because we’ve had the head almost overflowed in the past while healing over.

Test all bilge pumps, electric and manual.

Weather, Route, and Crew Readiness

Finally, step back and think beyond the boat.

Review multiple weather sources and understand the forecast trend, not just the next 12 hours. Make sure you have identified backup anchorages along your route. Confirm fuel range with a conservative margin.

Secure the interior: lockers latched, move heavier items low, nothing that can fly in rough seas. Communicate with your crew or family what the plan is. And if you have a baby or toddler, ensure that you have plenty of toys, diapers, snacks, water and wipes accessible in the cockpit with you.

Food

Not so much boat inspection but you will need to be well fed to deal with any issue that comes up. Cooking below deck when the weather turns making for a rough sail can be extremely strenuous. I personally like having easy snack food readily available and one pot meals pre-cooked. I don’t have to spend hours below deck trying to juggle my own balance, the needs of my two toddlers and potential sea sickness.

If everyone has a full belly everyone is much happier and less sick. Salt crackers and ginger ale or 7Up are great options to settle a stomach.

A Final Thought

Long passages don’t demand a perfect boat—but they do demand attention. It’s up to you to decide what needs to be addressed right away and what can wait for your next haulout or next anchorage. Run systems instead of just looking at them. Fix small issues while they’re still small. A careful inspection before departure is one of the simplest ways to turn a long sail from a stressful gamble into a confident, enjoyable passage for everyone on board.

Alex

Cory and Alex share their adventure with weekly videos on their YouTube channel “Wildly Intrepid Sailing”. Their dream is to travel the world and to live without regrets.