Things I Wish I Knew Before I Went Cruising

Cruising is the act of getting in your boat and going somewhere. Some people do this for a weekend, some people do this for a lifetime, but in the end, we are all just voyaging in a boat.

Back in 2012, when I first purchased Wisdom, I didn’t really know what I was doing, cruising wise. I lived aboard in a marina in Baltimore and dreamed of living on the hook, and eventually cruising, but I was afraid of the unknown. This is a list of things I have learned over the past 1.5 years of cruising that I wish I could tell myself back then.

Untie the lines

When I lived aboard in the marina, I always dreamed of living on the hook. I thought it would be so cool to anchor somewhere new every week and get back and forth to the boat by dinghy. To me this was the first step towards cruising.

I would go sailing every weekend and anchor out, but I was always in a rush to get back to the marina by Monday morning so I could commute to work.

What I should have done is stayed in an awesome creek that I loved and brought the car to there!

I didn’t have to get back to the marina, I could have just stayed at anchor, but I was afraid. Leaving the boat anchored in a calm and very protected anchorage was a foreign concept to me and I wasn’t ready to untie the lines. This meant that I was unnecessarily tethered to the pier and wasting marina fees that could have been saved up in the cruising fund.

When we went cruising, we had the good fortune of living on the hook for the first year as we made our way down the East Coast of the United States. Life on the hook is THE BEST! Granted, there are places that living on the hook is better than others. Some creeks in Maryland are surrounded by private land and there would be absolutely no feasible way to get to your car without trespassing on private property. Sure, you might get away with this on the first day, but the people will wise up and be waiting for you, and the gig will be up in a bad way!

Look for waterways that are cruiser friendly and live there. If you are uneasy with the idea of leaving your boat unattended at anchor, find a marina with a mooring ball field. What you want to do is get off the dock and out into the water. You need access to a public pier and some place you can leave your car (if you have a car). Explore a little and find a great spot, and don’t be afraid to ask someone with a dock if you could pay them a fee (weekly or monthly) to tie your dinghy up to, or maybe even to park your car in their drive way. This will cut your costs and give you the freedom you have been searching for.

Get a good dinghy

Your dinghy is your connection to shore, and it better be a good one. My first dinghy was a cheapo plastic shell from West Marine. I bought it used from Craigslist for $300. It was a waste of money. The thing rowed horribly and the box design towed terribly!

I then upgraded to a 13 foot wooden boat from Chesapeake Light Craft. This dinghy didn’t fit on the deck but towed well and rowed incredibly well. We used this dinghy for several years and for the first several months of cruising.

We changed dinghies because the 13 foot dinghy didn’t fit on the deck and towing a dinghy all the time is not very fun. We downsized to a Livingston 7.5 foot catamaran dinghy which did fit on the deck.

The Livingston towed well enough, and rowed well enough, but it’s best feature was by far the ability to ride on our deck! We took this dinghy all the way to the Bahamas, where we lost it because we were towing it in bad weather.

Don’t tow your dinghy in bad weather

This is a recipe for disaster. The dinghy will get tossed around and will either flip or get swamped. The result is the dinghy will then over stress the painter and break the line. Dinghies disappear quietly, and in the bad weather, you won’t be able to spot it among all the white caps and waves. This is an excellent way to loose your dinghy, so don’t do it!

Rowing is fine, but outboards are nice

Outboard motors are expensive. You need to buy them, and then you need to fuel them!

Oars, are cheap and will always work. We rowed for a year, even up to a mile from shore, instead of using a motor because we had oars and we didn’t want to have the expense of a motor. In the Bahamas, we salvaged an air-cooled Honda 2hp outboard and began using that to power the dinghy.

What we learned from this is that oars work just fine, but an outboard motor is nice! You can get places quickly, and you can go at any time you want without waiting for slack water.

Don’t stock up on food when you start cruising

I made this mistake. I thought that I was going to leave Baltimore where I had several grocery stores around me, and set off into the desert of a world with no places to buy food. I needed to have a lifetime supply of canned food on the boat so that I wouldn’t starve to death!

Everyone eats, and if you need food, go to the grocery store. There are these really cool devices called smart phones where you can search for grocery stores near you, and I can assure you there is always one within walking distance from any civilized anchorage.

One of my favorite places to anchor out was Harness Creek on South River. I liked it because I felt like I was “so removed” from society. There are a few mansions on the water and then trees forever! The place feels like you have been teleported to a new world and civilization is gone. Yeah, we were anchored in there for a few weeks when we started cruising and there is a grocery store about 15 minutes away from the anchorage.

Don’t do a big grocery run before you go, just untie the lines and be happy. When you run out of food, go ashore and get some more.

Don’t stay in the same state

Each state has it’s own flavor of cruising, and this is very apparent based on the laws that govern the waterways. Maryland is a state where the property line is dictated by the high tide water mark. This means that at high tide, there is no public land to walk on by a house. At low tide, all the land that has been uncovered is public (and you can walk your dog here legally).

Virginia sets the property line based on the low tide mark, meaning that there is no public land in front of a house. Maryland and Virginia also don’t have much in the way of public piers or good shore access from the water. It almost feels like they don’t want people living aboard in their waters. If you are in these areas, consider finding a mooring field to live in, as this gives you some rights when a land owner complains and the marine police come and start hassling you.

North Carolina is the most friendly state in our opinion. Everywhere we went, there would be wonderful free docks for us to tie up our dinghy and come ashore. The towns almost wanted us to come ashore and spend our money on groceries, meals, and supplies!

South Carolina was almost as inviting, but the dinghy docks required a fee.

Florida, while people talk about them cracking down on anchored boats, seemed really cruiser friendly! They had many free docks where we could tie up, even with free buses that would make stops right at the free dock! The boats that seemed to get hassled were the derelict looking boats, you know, the ones that you see listed on Craigslist for FREE. We take pride in our boat and make sure she always looks spiffy when she is anchored and we never had any problems with the police while we were anchored. That said, we did see the policy “check on” a dismal looking boat that was anchored next to us. The owner of the boat would yell at the police to “stop harassing him” which would usually lead to a morning show in the anchorage.

Keep your boat looking nice

You are judged by your boat. If your boat looks like a dump, people won’t want you near their stuff. They will fear that you are going to steal stuff and will frequently call the police on you. If your boat looks nice and you make yourself look presentable, people will usually invite you over for a meal and will want to get to know you! Appearances are what you are going to be judged on, and first impressions really matter.

Get an education

Educations come at a price. The price tends to be insane student debt but the result is the ability to land a job that you can work and go cruising. I went to college from 2004 to 2008, then dental school from 2008 to 2012. I graduated with a hefty sum of student debt.

The result is I earn enough money when I work to afford to buy items for the boat. This means that I can afford a nicer boat and it doesn’t look like a homeless person living in a free boat. This also means that I can work for a short period of time and afford to go cruising for an extended amount of time.

While we were cruising, we came across many many cruisers in the ICW. It seemed that there were two categories: No education and educated. The ones with no education were in 20-some footers with tarps over the boom (also called the liveaboard tent) and had no money for anything. Police frequently badgered these cruisers because the locals would complain about them. When these people pulled into port, the locals knew they had no money and were not going to offer anything to the town, but instead feared that they might rob from the townies. These people were all very nice and would not commit such forms of crime, but they were broke and they couldn’t afford to experience the towns they stopped in.

The educated people would show up on boats that were larger and much nicer. The boats were well cared for and the locals would welcome these people into their towns. Our interactions with police were always pleasant and usually involved them giving us advice on things to see in the town or places to eat! Having a degree also helps if anyone questions who you are or what you are doing. We arrived in one town after dark and were trying to find a (cheap) restaurant to eat in. A local saw us looking around the town and asked us what we were up to. At first they seemed suspicious and rather defensive, but once I introduced myself as Dr. So-and-so, they became totally relaxed and actually helped us find a great local restaurant that was still open!

Don’t wait

I waited for 5 years to go cruising because I always thought of another thing I needed to do before I could untie the lines and go. Truth is, the boat is still not ready to go and we have crossed an ocean! Once you have the basics (good ground tackle, good steering, good rigging, good sails) you are ready to go!

All that waiting was unnecessary because once we set off, it was amazing! Had Maddie never pushed me to go, I would probably still be in the marina coming up with more and more projects that I “need” to finish before we could go. When you are actually out there, you will figure out what you need, and you will then make it. If you prepare for every hypothetical case, all the time spent preparing for the things that never happen would be a waste of time. Do what you need as you need it so that you can get out there sooner.

Don’t buy electronic devices

Chart plotters look cool, but they are a waste of money! Anything that your fancy chart plotter can do, your phone can also do with a much cheaper app. Chart plotters, as well as other electronic devices will depreciate so fast, that they really become worthless and a waste of your valuable cruising money.

Even more of a waste of money than chart plotters are electronic autopilots. They are very expensive to purchase and to operate! They draw so much electricity that you will either need to run your motor or generator to keep them powered. Best off is to buy a reliable wind steering system that will let you keep your course without drawing endless amounts of power from your batteries.

Yes, a Monitor Windvane will cost you around $5,000, but that is a one time purchase! The unit will then run flawlessly forever without ever drawing a single amp from your batteries. Best of all, it is a simple system that works with ropes (something you are going to be very familiar with) so if something fails, it is easy for you to repair promptly and inexpensively.

Electronic autopilots might seem like they cost less than $5,000, but they really end up being too expensive to operate and you will never use it once you get a good wind steering system. Save your money and buy a Monitor Windvane. If you can’t afford it when you set off cruising, stay coastal and hand steer until you can save up and make the purchase. Then you will be ready to head offshore and have it steer you the whole way across the ocean!

The only electronic device worth getting is a good radio with integrated AIS. This will take all the guesswork out of sailing by night as well as navigating your way across busy shipping lanes.

Any other electrical gizmo that you can imagine is a waste of money and you should avoid falling into that dark hole of “gadgets that you need”.

Don’t sail close to shore

Shore is dangerous, that is how you get beached! Stay as far from land as you can. If you are tired, don’t force yourself to stay at the helm. If you have to stay close to shore and get tired, either anchor or trade watches, but do not risk falling asleep at the helm. One small mishap and you could find yourself looking at a hefty salvage bill!

Go Now!

I know this list sounds like a bunch of “don’t do this” and “don’t do that” but these are all mistakes that I had made and it would have been nice if someone had told me NOT to do them. Knowing this would have saved me time, money, and headache!

The most important thing that I wish someone would have told me is to just go now! Life is short and we should enjoy it to the fullest. If cruising is something you want to do, then go do it!

Just start small and as you feel more and more confident, you can then take further and further steps in your cruising career. You don’t have to make your maiden voyage an ocean crossing. Just take a weekend in a creek and venture off from there! A great place to really get a feel for cruising is the ICW. You really become self sufficient while you are in the ditch, and if you need food, repairs, or entertainment, it is only the next town away! We really grew the most in the ICW and found that cruising is a lot easier than we thought it would be. Maryland isn’t really an easy place to cruise, and neither is Virginia. The water is too isolated from the land. The ICW almost seems inviting to the prospect of cruising. Designated anchorages are easy to come by and the worst weather you can see in the ICW is nothing compared to being in the Chesapeake Bay or the Atlantic Ocean.

Get going and have fun cruising!