Begin any overnight adventure with a game plan and lots of prep. Beyond going through your preflight checklist to make sure everything on board is working, here are our own tips from many happy nights sleeping aboard boats both large and teeny:
Pre-start. If you're anxious about your first night on the boat, plan at least one overnight at the dock as practice. Pretend you can't go ashore.
Practice makes (hopefully) perfect. Sure, you know your way around your boat, but practice anchoring, docking, and tying off in the daylight before trying it at night. You don't want to drop the anchor for the first time when it's dark and you're stressed.
No moonshots, please. Don't go too far. Make it an easy, safe, stress-free trip. Avoid a harbor with poor holding, big surge, lots of current, or traffic.
Watch the weather. Of course you will. But forecasts change daily, if not hourly. You don't want surprises.
Plan B. Be ready with alternate destinations if wind, current, or weather make your chosen spot unfavorable.
Check (and recheck) your supplies and lists. The last thing you want is to be snug and secure at anchor, then realize your phone charger is still on the bedroom nightstand. Or you forgot the coffee. Consider how good your favorite pillows from your bed will feel on this adventure. If you're going to overnight at another marina, make sure you have a shore power cord. Check to see that what you're going to use is working (stove, potable water pump, anchor windlass, lights, head).
Provision wisely. Think through your menu. Fully prepare as many meals as possible at home (especially smart on a small boat). Chili that just needs one pot to warm up, poached salmon that you can put on mixed greens and serve room temperature. Keep it easy. And spice it up! Zipper bags are great for a few favorites from your spice rack.
Consider two coolers. If you don't have an on-board fridge, one cooler for frozen goods and a second that will be opened more frequently for cold goods should more than cover a long weekend. Frozen half-gallon jugs provide extra (and cold) freshwater when they finally melt. For longer stays, consider getting dry ice in your frozen cooler. Bottom line: Take plenty of water.
Safety first. You should already have your safety gear aboard. Check your life jackets, including a throwable, first-aid kit, flashlight, signaling device, fire extinguisher, Unlimited Towing from BoatUS (just in case). Create an emergency plan, and be sure to tell key people where you're going, how to reach you, and when you plan to return.
Stay put. Do you have the proper-sized anchor to hold if the wind pipes up? Be sure your anchors are right for the bottom where you plan to visit. Consult charts or other resources to learn the bottom and what anchor holds best to that bottom. Check if your anchor light is in working order, and use it every night.
Don't be afraid of the dark. Add battery-powered lanterns, a high-beam flashlight, and a bright LED headlamp — invaluable for a trip to the bow to check the anchor (to keep both hands free) or even just for a walk to the marina's bathroom. Bring extra batteries.
It may be colder than you think at night, so bring loose pants and a fleece sweater, even in warm climes.
Start the trip in daylight. As it gets gradually dark, your eyes will adjust. Turn down the brightness on instrument displays. What's good during the day will be blinding at night. Preserve night vision by using a red or blue light to look at the chart or pilot book.
Protect yourself from bugs. Mosquitoes, no-see-ums, and other bugs are not invited!
Do you have an extra handheld VHF? Bring it.
Head games. Make sure you know how to use (and unclog) the head. If not, it's the quickest way to cut short an overnight.
Night light. Bring a little LED camping light to give ambiance to the cockpit without using onboard power.
Bring a sun-shower bag for easy hot-water cockpit showering.