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THE DAY EACH YEAR that I put the boat away for the winter has always been a bummer. For many of those more than 30 years, I dreamed of taking the boat to warmer climates rather than to winter storage. You could call it my Search for Endless Summer. Last October, we started that search.

The dream is not unique. Dozens of boats from this area make the trip south by water, but I had never ventured beyond Starved Rock State Park on the river. The route starts with the Chicago River, then the Illinois River, Mississippi, Ohio, Tennessee-Tombigbee Waterway — bringing you to the Gulf of Mexico near Mobile, Ala. The water route to the Gulf covers roughly 1,200 miles. It is about one-quarter of the Great Loop that brought us back to Chicago via the East Coast and Great Lakes this spring.

My wife, Sharon, has never liked cold, and, over the years, I’ve grown to disdain it more and more, so taking the boat to Florida now (and back in the spring) made sense from that standpoint. There are reasons not to make the trip — the most obvious being it would be a lot cheaper to hop a plane. However, it is something we wanted to do just once in our lives. I’m fairly certain fuel won’t get cheaper and even more certain we won’t get any younger.

We encountered boats of all sizes and people of all ages making the Loop. It became apparent that just about any budget could be adapted to cruising the river, although the older the crew, the more likely creature comforts won out over pure adventure. In our case, creature comforts were near the top of the list. Our boat, the Heidi Ho, is a 50-foot Sea Ray.

Preparations and provisions were more time consuming than I expected. We’ve read a number of books and guides on the rivers trip. Getting three sets of charts — one paper and two electronic — was more involved and more expensive than I expected, but redundancy is important. We carried more food than necessary, but used a lot of the cold weather clothing we put aboard. I added the luxury of satellite TV to keep us closer to news, markets, weather and such.

Since the trip would take at least a month, plus play time in Florida, it seemed an appropriate time for me to retire from regular news broadcasting at Chicago’s WGN Radio. A Web site (www.mynewspod.com) was modified so I could do daily blogs and receive e-mails from WGN listeners.

I noted a number of boaters sent e-mails about mechanical issues along the Loop, so I asked Cummins Diesel technicians to check the engines and generator prior to our leaving Chicago.

Departing on Oct. 11, our proposed itinerary called for us to be on the water two days at a time and laying over the third day, for rest or to use the spare day to make up time in case of weather or other unforeseen delays. That formula could get tossed when we got into areas of scenic or historic interest — or extended bad weather.

Our trip downriver coincided with full autumn colors, and it became clear that, even with the built-in flexibility, we allowed far too little time to really enjoy some of America’s great river scenery — some of it right here in Illinois.

Part of our timetable was predicated on insurance coverage. Boat insurance stipulated the Heidi Ho could not be in the Gulf of Mexico before Nov. 1, which the insurance company considers to be the end of hurricane season.

Departure day from Chicago’s Burnham Harbor was cold, blustery and rainy — a nice reminder of why we wanted to go south. It snowed our second day out. Another reminder.

Getting through heavy barge traffic on the river and waiting for locks slows cruising the upper part of the Illinois Waterway. We waited for five hours at the Dresden Locks near Marseilles, because a barge got loose in the lock during strong winds. I already knew commercial boats took priority over pleasure boats in the lock process, but we had frequent reminders as we went through 27 locks between Chicago and Mobile. It should be noted that the men and women who make their living on the rivers — the barge crews, captains and lock personnel — were courteous and helpful toward pleasure boaters, even when the pleasure boater might not have deserved it.

We didn’t stop at all the small river towns of the lower Illinois River that seemed inviting. Many of them have embraced their rich river history by restoring the riverfronts. Among our favorites were Havana and Grafton. Havana’s Tall Timbers Marina is just a short walk from downtown. The owner of Tall Timbers and his wife both have full-time jobs to support their “labor of love” redeveloping the marina.

Grafton is where the Illinois empties into the Mississippi. The town has a new and busy marina, but boaters were a minority of tourists in the small town. Grafton has adapted well to river town tourism. I base that assessment on the number of ice cream stores and the number of shops that sell T-shirts with clever and not-so clever slogans.

The lower Illinois River runs through a contrast of towering bluffs and wetland wildlife preserves. Likewise, the Mississippi above St. Louis features majestic bluffs. However, St. Louis from the water is a disappointment. When moored barges are not blocking the view, industrial warehouses line the riverbanks. The lone exception is the beautiful park containing the famed arch. But there is no pleasure boat access to downtown St. Louis. Seems strange.

Nearly all pleasure boats heading south stop at Hoppie’s Marina at Kimmswick, Mo. Hoppie’s is about 20 miles south of St. Louis and consists of a couple of small barges at the river’s edge. Not much to look at, but a welcome spot to fuel and spend a night or two while visiting the delightful small tourist town of Kimmswick. Another reason to stop at Hoppie’s is to get the daily briefing from Fern Hopkins on what to expect downriver. Fern, her husband and daughter run Hoppie’s. They are a pleasure to encounter on the Father of Waters.

After Hoppie’s, the Mississippi River has few facilities to offer pleasure boaters. It is one of the reasons to turn up the Ohio River at Cairo, Ill., and travel to where the Ohio greets the Tennessee or Cumberland Rivers. We chose the almost-deserted Cumberland, despite being 50 miles farther, to avoid delays caused by commercial barge traffic locking through on the Tennessee.

After going through the Cumberland River locks, we were in Lake Barkley. It and Kentucky Lake to the west, which was formed by the damming of the Tennessee River, make up a huge recreational area known as Land Between the Lakes. Grand Rivers, Ky., is the small vacation town nearest the marina where we berthed. Patti’s 1870 Settlement restaurant is well-known for its two-inch-thick pork chops and Levee High Apple Pie. Yes, we can attest to the outstanding qualities of both.

As we left the Green Turtle Bay Resort and Marina early on a Saturday morning, we were confronted with dozens of boats coming through the canal that links the Cumberland and Tennessee Rivers. They were beginning a bass tournament. We cut back our speed, going the opposite direction of these 40 and 50 m.p.h. machines. There were no incidents, but I watched as several of the speeding bass boats went airborne as they crossed the wake left by our boat. It had to reset their dentures or other parts when they landed. Bass boats that slowed while passing did not face that punishment.

I had been on the Cumberland River years ago, but this was our first time on Kentucky Lake and the Tennessee River.

The autumn beauty was spectacular. With many places to anchor or dock, we could easily have spent more time there. However, the wide-open waters and few barges were also an invitation to make progress toward the Gulf. We stopped at Cuba Landing, near Waverly, Tenn., for fuel and a night’s stay.

When we asked about nearby restaurants, the owner said the closest one was 7 miles and it wasn’t very good. But he invited us to go with him to the “best place for pork chops in the county.” He drove some 20 miles in his Escalade while drinking an adult beverage. Sharon was not amused. The destination was a rural bar where food was an afterthought. However, the colorful characters and conversation made up for what the food lacked.

Pickwick Landing State Park seemed the closest place to dock to visit the Civil War battlefield at Shiloh, Tenn., though the battlefield comes right to the water’s edge. Because we had no car, the marina personnel directed us to Larry Deberry as a guide for the battlefield tour. He is a native of Shiloh, as were his forefathers. The tour commentary favored the Confederacy, but was still educational.

Midway Marina is where I stepped off the boat in the early morning and onto a dock covered with black ice. Came close to sliding off into the water, except for some major acrobatic motions that I didn’t know I could do. After that a night in Demopolis, where I learned from a towboat captain that WGN on the side of barges means Warrior Gulf & Northern — not World’s Greatest Newspaper.

Bobby’s Fish Camp in rural Alabama is a recommended stop at least once. It is the last fueling stop before Mobile, plus Bobby’s restaurant serves catfish, hush puppies and other Southern-fried fare. Not bad if you eat while the food is hot — before the oil turns to a solid.

It was raining most of the time we were at Bobby’s, and the area was under a tornado watch. I double-tied the dock lines, but the skipper of the only other boat at Bobby’s offered the observation that the docks did not look like they would withstand a strong wind.

The weather cleared without incident and we finally left Bobby’s about noon, trying to reach Mobile by evening. Our destination was Dog River, about 10 miles south of downtown Mobile. However, it was getting too dark to see the navigation markers, so we turned back and tied up to the Mobile Convention Center. Between the current, north winds and tugboat traffic all night, there was little sleep. Not a recommended stay.

The next morning, in the security of sunlight, we easily cruised down Mobile Bay to Dog River Marina. My mother and sister drove over from Hattiesburg, Miss., for a day of visiting. That included touring the Bellingrath Gardens. Bellingrath is a mansion surrounded by acres of beautiful flowers and shrubs. Quite a sight.

On Halloween, we crossed Mobile Bay to Fairhope, Ala. The marina loaned us an old pickup truck to drive into this neat town. The merchants were hosting trick-or-treating for kindergarten children. The children had fun. The adults had more fun. One of my favorite photos from the trip is the sunset taken off the dock.

Sharon left me in Fairhope, not wanting to venture into the Gulf. Our son came to take her place as navigator. We spent three days getting to St. Pete Beach, Fla., with stops in Panama City Beach and Crystal River. Two of the three days, the waters of the Gulf were like glass. The other day had the potential to be very rough, so we stayed fairly close to shore.

A week later, I returned to take the boat from St. Pete Beach to her winter slip in Ft. Myers.

A number of e-mails from WGN listeners said they, too, dreamed of taking the trip, but hadn’t yet for one reason or another. But perhaps the most telling ratification was from a listener who e-mailed me on the way south saying her father always wanted to make the same trip, but kept putting it off and died before he could realize his dream.

It is a lesson in living your dreams.

I know I’m lucky to have lived one of mine.

———-

Lyle Dean took retirement last fall from his 50-year career in radio — nearly half of which has been at WGN Radio, Chicago. He holds a U.S. Coast Guard Master’s (Captain) License. Sharon Lebsack retired as a risk manager and registered nurse at Rush University Medical Center in Chicago. They brought the Heidi Ho back to Chicago in the spring of 2007, but that’s another story.

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IF YOU GO

Cruising America’s Great Loop is not akin to brain surgery, but being prepared and remaining alert will make it even easier.

The nice part about doing the Loop is that many people have already — and are currently — making the trip. They generously share their experiences and expertise in various ways.

The best way to tap into their knowledge-base is to join America’s Great Loop Cruisers’ Association (www.greatloop.com). An e-mail network is available to get information about the waterways, locks and dock facilities, food, fuel, etc. Initial membership is $45, though you can use their Web site without charge to get information about printed guides and navigation charts, as well as checklists for first-time cruisers. It also has links to blogs of “Loopers” that are always informative and often entertaining. Charts and books are also available on the Internet or at boating supply stores, such as West Marine.

www.mynewspod.com has the author’s account and photos of the trip by calendar date, starting Oct. 11, 2006; click on “The Lyle File” at the bottom of the page.