Embarking on an extended cruising adventure requires preparation not just for the journey itself but also for leaving your life on land well-organized. Whether you're setting sail for a few months or venturing into the great blue for over a year, ensuring that your home and financial affairs are securely managed in your absence is crucial. From securing your residence against the elements and potential security risks to automating bill payments and managing your mail, this guide offers a thorough blueprint on how to confidently transition from landlubber to seasoned mariner without leaving loose ends.

Preparing Your Home

Home Security System

This depends on your comfort level in leaving your home unoccupied for nine months. I wanted a security system for peace of mind with a temperature alarm if the house temperature dropped below 50 F since we live in the cold northeast with occasional power outages. It's monitored 24/7, and the security company has instructions on how to enter the house if the system needs repair, which has happened twice in the last ten years. The neighbors do not like a house alarm going off in the middle of the night! My system was professionally installed, but some do-it-yourself kits are out there. One up-and-coming company Is WYZE Home Monitoring, which also makes webcams (see next item) that I use and like.

Webcams for the Home (and Boat)

When away from home, I like to check-in to see how things are at home (is the driveway plowed so the fuel truck can get in, any packages delivered in error to our home address, any trees down, etc.). Nothing beats having a few webcams scattered around the house with views of the driveway, backyard, back porch, and a few inside the house. The webcams only require a WiFi connection via a router. You can look through the webcams in real-time or from photos triggered by motion detection. They can be viewed with a smartphone or tablet over the internet. For outside use, I position the webcam to look through a window, although the latest ones from WYZE are waterproof.

The world of webcams changed forever with the startup company WYZE webcams that produce HD video even in starlight at night. All that is fine, but what sold me was the super-easy setup. You aim the webcam at a QR code displayed on your iPhone, and the Wyze app automatically connects your new webcam to your internet connection! The last two weeks of activity that triggered the motion sensor are automatically uploaded to the cloud for viewing with a smartphone or tablet anywhere you have an internet connection for a small charge. It also accepts an SD card that records everything, 24/7, for viewing at a later date. The photo above is from one of their webcams showing a car driving by. There is some barrel distortion, but the clarity is excellent at 1080p. I have eight cams scattered throughout the house, looking inside, and outside to the yard.

Antifreeze Your Furnace

I know of two instances where friends of ours have come home to a flooded basement and water all over their house after a power outage in the winter. They had baseboard water heating and the pipes burst when the house temperature dropped below freezing during a power outage in a winter storm. When power returned, and the furnace turned back on, the baseboard heating water just poured out of the burst pipe. I had antifreeze added to my heating system by my local oil dealer, so no more worries about burst heating pipes.

Tip: Monitor for small leaks when first installed: glycol can leak where water won't; just tighten it. 

Turn Off House Water

Antifreeze in your water heating lines won't prevent burst pipes in your house water lines unless you turn off your water and drain the pipes. I installed valves in the basement to turn off all house water with a single valve. I also turn off the electricity to the well pump when we leave so even if the pipes from the well burst, the basement won't fill up with well water. But, as the ads say, there's more! You must also turn off the supply water to your dishwasher, washing machine, and refrigerator (also turn off the ice maker, usually a separate switch inside the freezer). These three appliances usually have one-way solenoid valves. That means they open via a solenoid but depend upon external water pressure to close. If the water pressure drops below 20 psi (typically), the valve will open and allow water in the pipes higher than the valves to flood into the appliance if the water is not completely drained from the second floor. I'm told this is a common insurance claim for dishwashers which have a small capacity for excess water. If you're still unconvinced, see Pete the Plumber.

Set Up Automatic Forwarding

You use USPS first-class mail forwarding to another address (e.g., son or daughter) for six months, renewable for another six months if needed. There is no charge for this service from the USPS as long as you don't sign up for their premium forwarding service, which I don't recommend. You should buy a supply of prepaid Forever Priority Mailers so your son or daughter can send your mail to a marina of your choice before your arrival. We haven't been to a marina yet that wouldn't accept mail for transients. If the contents weigh more than 12 oz, then the package has to be taken to the nearest post office for acceptance instead of leaving it in your mailbox. This rule started after 9/11. There is still no charge for any weight up to 70 lbs, and it comes with free tracking from USPS.

There is one fly in the ointment here: if the sender adds "Return Service Requested" on the outside of the envelope, the post office will not forward that mail but will return it to the sender. I had a lively conversation with my dental office who kept getting their bills sent back to them – not forwarded to my son in Connecticut. The secretary swore that the letter did not have "Return Service Requested" on it (which it didn't). However, the outside of the office envelope she used did that offending phrase. Once she used a plain envelope, the bills were forwarded as expected.

Tip: Be sure to sign up for Informed Delivery (it's free), which sends you a daily photo of your mail before it's forwarded, useful if you're looking for an important document to arrive like your boat registration.

Have a Yard Keeper

You still need your yard mowed and driveway shoveled even when you're down south enjoying the sun. You don't want your house to look unoccupied, but I do it so it looks nice. I've heard that there's snow in the wintertime (haven't seen it for ten years...) so arrangements have to be made so fuel oil can be delivered for your furnace. This also requires shoveling out the inlet pipe manually; the oil delivery person usually won't do that.

Make Arrangements for House Entry

Sometimes, a repairman or someone you know must enter the house to fix a problem. You need to make arrangements for a key somewhere. You can always give the security system code over the phone, although my security system and oil furnace company already have the code. Twice we've needed the furnace repaired and twice the security system needed a sensor replaced. Besides, I get lots of photos of their work over my internal webcams, and they wave! Even if an intruder finds the key, he still needs to know the disable code for the alarm.

Tip: of course, hide a key, but not under the welcome mat! You're still protected if you have a house alarm, but a repairman does need entry to fix a problem.

Turn Off All House Services

We turn off the newspaper delivery and trash pickup while away. I don't have cable anymore but I do keep the internet running so I can view the house cams. You don't want newspapers piling up on the lawn.

Tip: some newspaper carriers put a yellow or blue dot on the mailbox to remind them you're not home – but that practice also advertises to potential thieves that you're away. Don't let them do that.

Get Rid of All Food

It's amazing what can be done with leftover boxes of food no matter how well sealed given nine months of work by hungry little critters. If there is something you must keep, put it in the refrigerator, which I leave plugged in. The oven and dishwasher are other choices for storage. We put all the dry goods we don't take along in coolers or plain bins with tight lids. One year I forgot my advice and left a 20 lb bag of dog food in the garage, unopened. Upon returning in the spring, I lifted the bag and found it weighed much less than I remembered. I checked the top, and it was still sealed but then I noticed a small hole in one corner – uh oh. The mice had a grand time converting the contents into new mice. Live and learn, once more.

Turn Down the Heat

I set the house at 60 F, which is probably higher than needed but it's what I choose. Much lower than that, and the refrigerator has a problem according to the manual. I also put the boiler temperature on the furnace to the lowest setting recommended by the manufacturer to save on fuel oil.

Notify the Sheriff

Most localities will offer to check your house while you're away. We've seen them check our house on our webcams, so we know they come by.

Leave Contact Info with a Friendly Neighbor

Someone who's near your house all the time can keep an eye out for anything unusual and give you a call (Why is that moving van parked in your driveway? Are you moving all your valuables somewhere else?)

Preparing Yourself and Your Finances

Now that you've taken care of the house, how about you? You want to enjoy the trip, not be burdened with things to worry about.

Automate Your Bills

We have our mail forwarded to my son, who will periodically send them along to one of our stops at a marina, but it's easier to have the bills automatically paid. You can arrange to have companies (electric, phone, internet, fuel oil, etc.) automatically deduct the payment from your checking account or charge your credit card automatically.

Tip: use a direct deduction from your checking account vs an automatic charge to a credit card. If you have a credit card canceled or renewed (new expire date), it's a pain to go over all your automatic charges at all the different websites and update the credit card details.

Tip: set up an account with your local bank where you can enter a bill and get a check sent for payment with no check writing required and no first-class stamp needed for those cases where automatic payments don't work.

Tip: All banks offer some form of remote check deposit. You take a photo of a check you want to deposit (already signed) with their app, and within minutes, the bank credits it to your account.  

Use Quicken for Financial Records

Quicken used to be the only game in town when you wanted automatic updates of all your accounts in one place, but now most banks offer the same service for free. Quicken is still king if you want to keep your records long-term, but if that's not important, use your local bank's service.

Enroll in TaxAudit and use TurboTax or equivalent

So, you're in a remote anchorage somewhere on the ICW, and during a conversation with your son, you hear that a letter from the IRS arrived a few days ago with a reply due in two weeks via snail mail! You're already late. If you want to dispute the audit, how do you do it via snail mail while on the ICW? With a service such as TaxAudit, you never communicate directly with the IRS. The service handles all communications and will work with you via e-mail and phone and answers all the mail questions sent by the IRS. The IRS only wants to communicate via snail mail, which is difficult on the ICW.

I've had two tax audits. In the first case, I made a mistake, which the IRS thought resulted in me owing them money. During the tax audit, it came out that the error was in my favor, and the IRS owed me money! It took two years (!!) for me to collect from the IRS, but when they thought I owed them money, they wanted it in two weeks! Tax Audit handled the multiple court appearances required and communicated via email to keep me appraised of their progress. In the second case, the IRS claimed the deduction for interest on my boat loan was not valid as a second home. I emailed documentation to the audit service, and they handled all the communication with the IRS, and I won the case. The audit service coverage is the best tax money I ever spent. You can pay for it within TurboTax or directly at their website.

Tip: if you get a letter from the IRS when using this service, do not answer! All communications must take place between the IRS and TaxAudit, which is much easier. Tax Audit is out of the loop if you reply to the IRS directly.

Scan All Medical Records and More

Make a habit of scanning all essential documents and storing them in a file that syncs automatically to your laptop, iPad, iPhone, or equivalent. Any all-in-one printer includes a scanner that works fine such as the Epson EcoTank ET-2850 or the Canon PIXTMA TS6420a. Later on, I will recommend a file syncing system that syncs everything to keep all copies on all computers, laptops, iPads, and iPhones you own. If you have a medical problem on the ICW, it's invaluable having all your medical information already downloaded and stored on a readily accessible device such as an iPad that you can take to your doctor's office.

Spend a day scanning everything you keep in your desk files and wallet. For example, I have softcopy, meaning a PDF file or jpeg image of:

• Immunizations for your pet.
• Dog license.
• Passports.
• Drivers Licenses.
• Marriage Certificate. In a hospital, your wife is unconscious, "Who are you?" I know this is a little extreme, but why risk it? Keep a PDF copy handy.
• Living Will and Health Proxy for yourself and your spouse. Hospitals will ask for them.
• Social Security cards.
• House Insurance contract and coverage details. Your insurer will usually provide a PDF file for your use.
• Boat Insurance and coverage details. Most marinas will ask for proof of insurance coverage if you stay a month or more.
• Car Registrations. Some companies use car IDs as a second way of verifying it's you over the phone.
• Taxes submitted all years. TurboTax 1040s are useful for tax audits and can be saved as PDF files.
• House purchase papers in case you're challenged on a tax deduction for your house mortgage payments.
• Boat purchase papers. One year in Maine, I had to prove I paid NY state sales tax or else Maine wanted me to pay them!
• Boat registration and documentation for Coast Guard checks and some marinas.
• Dinghy license. Florida Wildlife Commission was checking one year for stolen dinghies.

Of course, I have a hard copy of my Passports, driver's licenses, social security cards, boat insurance, boat registration, and documentation. However, if the boat sank, I would still have everything I need since the files are not only stored on the laptop, iPad, and iPhone, which are all probably at the bottom of the ICW, but also in the cloud in my Google Drive, which auto-syncs between all devices I own. I was stopped by the Coast Guard twice in ten years. They were only interested in the boat documentation and whether we had any firearms on board. Oh yes, they asked if the dog was friendly! I don't recall them checking anything else.