How I found a chance to cruise the Hudson River, Erie Canal, and Great Lakes from New York City to Chicago — without my own boat.

A while back, I blogged about The Great Loop, a boat trip I wanted to take before I turned 65 — which is still a way off. With thousands of miles of river, canal, and even ocean to navigate over the course of about a year, it isn’t a trip to be taken lightly. Not only would I need a boat capable of making the trip — and yes, I’ve been shopping for one — but I’d also need to build a knowledge base and skills to be able to do the trip safely. Although my self-imposed deadline was still years away, I’ve learned that the older I get, the faster the years go. I can’t waste time dreaming about it. I need to get my rear in gear and get to work.

It Started with a Crew Wanted Ad

I started building my knowledge base by joining an organization that provides support for “Loopers,” as Great Loop cruisers are known: America’s Great Loop Cruisers’ Association. (I blogged more about that organization here.) The AGLCA’s website has a number of features, many of which require membership to fully access. While browsing through it, I saw that they had a classified ads section. And while browsing through that, I saw that there were listings for Crew Wanted.

I’d never really thought about doing any of the trip as a member of someone else’s crew. I’m a hands-on person and I guess I kind of like being in control of things I get involved with. But I definitely lacked many of the skills and much of the knowledge I’d need to take command of a boat on a cruise like this. Perhaps being part of someone else’s crew could give me the hands-on experience I’d need to learn a lot of what I’d need to know a lot more quickly than I would without access to a boat.

There were two ads and I answered one of them. It was posted by Capt Paul, an experienced boat captain who had a 27 foot Ranger Tug — coincidentally the same boat I was interested in buying (although he has the older inboard engine model). He set up a FaceTime call, which I soon realized was one of many interviews he’d be doing to find crew members.

The Interview

The interview lasted about an hour. We discussed what he was looking for and my qualifications for the position.

He was looking for two crew members to accompany him from his home in the Portland area of Maine to the Stuart area of Florida. I originally thought he just planned to go down the coast, moving into the Intracoastal Waterway around Chesapeake Bay. But no! He wanted to enter the Hudson River at New York City, take that to the current incarnation of the Erie Canal, and cruise various Great Lakes to Chicago before heading south of the Illinois, Mississippi, and other rivers to get to the Gulf of Mexico and then cross central Florida in the canal system there. In other words, he wanted to do about 2/3 (or more?) of the Great Loop.

Wow. That was a bit more than my mind could take in. It would be a long trip — maybe longer than I was willing to commit to? I wasn’t sure.

The arrangement would be cost sharing. I think he wanted two crew members not only to deal with the locks on the canals — which are notoriously difficult for solo boaters — but to keep the cost of the trip down. I thought immediately of my friend Bill as another crew member, but family obligations currently have him tied up.

We spent a lot of time talking about my boating experience. I didn’t realize I had so much until I had to brag about it:

• I grew up in northern New Jersey where my family had a series of small — think around 20 feet? — boats. We’d put in at the boat ramp under the George Washington Bridge and cruise on the Hudson. A common trip would go around Manhattan, but we also went as far north as just past West Point.
• I’ve been houseboating on Lake Powell twice: a 7-day trip and a 4-day trip. I did a lot of the driving.
• I’ve rented powerboats on Lake Powell, Lake Mead, and various other lakes and rivers throughout my adult life.
• I’ve owned a pair of Waverunners, which I used on various Arizona lakes and in the Colorado River on an epic overnight trip from Lake Havasu to Laughlin, NV.
• I’ve owned a small jet boat for the past 10 years, which I’ve taken on various rivers and lakes in Washington state and Arizona.
• I took a 12-day “Learn to Navigate the Inside Passage” cruise a few years go where I was one of just four passengers learning about cruising.
• I’ve been an active passenger numerous times on other people’s boats in various waterways, from inland lakes and rivers to the San Juan Islands.

I also have a huge interest and tons of experience in navigation, on land, on sea, and in the air. Maps have always interested me and I have good map skills, even in this age of Googled driving directions. Hell, I’m nutty enough to put nautical charts on my iPad while on big ship cruises so I can track where we’re going.

Anyway, we hit it off well enough. Capt Paul seemed like a no-nonsense guy and I’m all for that. I apparently didn’t come off as (too) flaky and my experience seemed to score some points. I probably scored more on enthusiasm and apparent financial stability. He mentioned other interviews and we said our goodbyes.

The Plan

A few days went by. I had a chance to wrap my head around the trip. Capt Paul sent a planned itinerary with dates. I had some time constraints — I couldn’t leave Washington until after cherry drying season ended, which was at least two weeks into Capt Paul’s trip.

In the meantime, he found another crew member willing to do the whole trip with him and another willing to join him in Chicago. I had to hustle or I’d miss out.

We started emailing back and forth about me going from New York City to Chicago with them. I really wanted to do the Hudson River — the cruising grounds from my childhood — and the Erie Canal. In fact, I pretty much decided that if I couldn’t do those parts of the trip, I’d skip it. After all, I was facing a big expense just getting out there and back and a lot of work finding someone to take care of my pups while I was away. I may as well do the trip I wanted to do.

We played with dates a little. I found a pilot willing to take over for me in my helicopter if cherry season went long. Capt Paul agreed to wait until August 10 to depart New York City. I could arrive the night before and meet up with him and the other crew member (Dianne) at Liberty Landing Marina. I bought plane tickets to get out there.

And then, when he sent out an email to all the folks who had applied for the crew positions to tell them he’d made his selections, I double-checked to make sure that I was one of them.

I was.

The trip is a go.

Some Closing Thoughts

I have a lot more to share about this adventure now and will have a ton more to share in the future. But I do want to share a few thoughts as I finish up this blog post.

I guess the main point I want to make is this: if you want something badly enough, you need to make it happen. This is something my wasband used to say to me when I was a twenty-something on a career path I hated in corporate America. I took his advice to heart and have been doing so ever since. If you know me and my history, you know that I’ve been making things happen for myself for the past 35+ years.

I was in a Zoom meeting with other Loopers recently — blog post to come about the AGLCA Rendezvous — and mentioned my upcoming crew duties. One of the attendees who was also shopping (with his wife) for a boat wanted to know how I’d managed to get the chance to do it. He sounded — dare I say it? — jealous.

I answered a classified ad, I told him.

You can’t just wait around for opportunities to present themselves. You have to look for them. And then you have to take action to make it happen.

If I hadn’t needed time to think about the possibility — and difficulties — of doing the whole trip, I could have had Diane’s slot — or maybe we could have both been crew members for the whole thing. That’s okay because I’ve bit off exactly what I wanted to chew this time around, but it also brings home the point that if I’d delayed at all, someone else would have had my slot.

If you want something badly enough, you have to make it happen. I’m making this trip happen and I can’t wait for it to start.