Day five–We transition to Milwaukee

by | Oct 3, 2026 | Photography

Not much to say about this day. After four days of perfect weather, we woke up to a torrential downpour. Cats and dogs time. We had another Starbucks breakfast (I had to go back and see Pablo), packed up, and I walked a couple of blocks in the rain to Enterprise Car Rentals, grabbed a great big Jeep Wagoneer, got lost on the way back to pick up everyone, and then we were on the road. To the right is the only photo I took with my camera all day. I am sure if it hadn't been raining cats and dogs, there would have been more. All the rest are from my phone.

I want to take a minute here to acknowledge Enterprise Car Rentals. I used to skip them because I just was not happy with them. I am not sure why, but I have kind of always rented cars like I buy some stuff. They are all as good as the other company. And for some reason, Enterprise was not my favorite. But they are now. The last three times I rented, it was from them, and pickup went well each time. But this time they outdid themselves. I had picked up the car in Chicago for a one-day rental at 9:30 am. That meant I did not have to return it until 9:30 am the next day. Also, when I picked it up, it had a quarter of a tank of gas. The manager at pickup told me to return it with a quarter tank, and we would be all set. I ended up putting just under half a tank in it and hadn't used that much of it by the time we arrived in Chicago.

I had also planned to keep the car until the next morning so we could drive to dinner, but that changed when I found out it cost $50 to park at the hotel and the restaurant was about four blocks away. So I decided to return the car early. When I got there to return it, the manager of the Milwaukee branch told me that since I returned it early, she was going to refund $50 of my rental, and she saw I had extra gas (above that quarter of a tank), so she credited me for that. Unbelievable.

You can drive from Chicago to Milwaukee in about an hour and forty minutes on Interstate 94, but we left Chicago at 10:30 and couldn’t check into our hotel in Milwaukee until 3:00 pm. So I was determined to drive along the shore of Lake Michigan as much as possible, which meant asking Siri for continuous directions to the next point north. If you tried to skip a spot on the shoreline, she would take you out to the Interstate because it was “faster.” We didn’t want fast.

So we drove through some amazing neighborhoods, saw a cool lighthouse, and wound up in Racine, Wisconsin, where we met Steve and Jamie for lunch at a local joint, the Bridge Tender Tavern, where I finally got that other Chicago iconic food (which Wisconsin claims belongs to them), the Tavern-style, cracker-crust pizza. Delicious!

After lunch, we finished our drive north to Milwaukee and to our home for the last two nights before we board the ship, Saint Kate—The Arts Hotel. This is a very cool hotel that is entirely FILLED with art. There is art everywhere. They have a huge gallery in the lobby, and there are art installations all over the hotel, including in every room. Also, in every room is a ukulele and a Victrola record player. Seriously. The hotel is beautiful, and the beds are vastly superior to those in the Airbnb in Chicago. Sadly, the pillows are horrid. More and more, I have come to believe that the older you get, the more you need to sleep in your own bed, which is a problem for those who love to travel.

We had reservations for dinner at Zerlattii, which the Eater website called “the best Italian restaurant in Milwaukee.” Apparently, there are not many Italian restaurants, so this one was just “fine.” Or maybe I am now ruined for all future restaurant meals because of our dinner at Rose Mary? Could be ?.

That about covers our transition day. I have a few rainy photos for you, and that’s it. I am including a few other photos I took with my iPhone as I walked back after returning the car and of the Saint Kate lobby to show you their cool galleries. But I am writing this at 4:28 am on Saturday morning. I am aboard Viking’s Octantis, and WOW! What a ship. More about that later. Not to mention our full day in Milwaukee.

 

Day four in Chicago—walk, Buckingham Fountain, Chicago Cultural Center, dinner and an Improv show at Second City

by | Oct 2, 2026 | Photography

This was our last full day in Chicago as we were heading up to Milwaukee the next morning. We had purposely not planned anything for the day so we could fill in what we had missed. I still got up early that morning and headed out to see what photographic opportunities awaited me. I walked about 3/4 miles to the Buckingham Fountain at 6:00 am, only to find it was turned off until 8:00 am. Had to go back later. But you can still see the photos below for the fruits of my early-morning traipsing around.

As for the rest of the day, Kathleen stayed in. We had already done too much walking on this trip for her poor knee. Mike, Cathy, and I went across the street to the Chicago Cultural Center to see the exhibits, but mostly to see the incredible building. I would say more, but this is a case where the photos and captions will do a better job. See below. Don't forget: if you click the first shot, you can scroll through using your arrow keys or by swiping. And PLEASE... don't look at my photography on a phone. Please... (WOW! I haven’t said that on this whole trip yet, but keep it in mind.)

After we visited the Cultural Center, we walked Cathy back to the Airbnb, and Mike and I set off to take photos of the Buckingham Fountain, which our guide on Day two told us was the largest fountain in the USA or the World…I don’t remember which. I am sure Mike will remind me. It is a pretty spectacular fountain. We got those (see below) and headed back because we had big plans for the evening.

First was dinner at Corcoran’s Irish Pub, which turned out to be our least favorite so far, especially after our experience at Rose Mary the night before. Just kind of sad. My brother Steve and his wife Jamie joined us for dinner and afterward. Afterward, we went across the street to see the current production of the world-famous improv troop—Second City. If you are unfamiliar with Second City, it is easily the most prolific contributor of cast members to Saturday Night Live. Dan Aykroyd, John Belushi, Phil Hartman, Tina Fey, Amy Poehler, Seth Myers, and a lot more started there. The show was knockout funny, and we had a great time. It didn’t end until around 10:00, and then we had a Lyft incident that I won’t go into, but it kind of capped the evening poorly. We had to get to bed because we were driving to Milwaukee early the next morning.

"I went down to Chicago to try to go into a place called Second City. I auditioned for that and got in pretty quickly, but I couldn't stop partying. They gave me a warning: 'If you do it again, we're gonna kick you off the main stage."—Chris Farley

Day Three in Chicago—walk, Architectural Boat Tour, lunch, Obama Presidential Center, the best meal of my life

by | Oct 1, 2026 | Food Experiences, Photography

The headline kind of says it all. I did my usual early-morning walkabout to take sunrise photos. I also used this walk to visit all the places we would go later in the day, like the Architectural Tour we would take at 9:00 am. Photos from this walk are directly below.

On my way back to the Airbnb, I stopped at Starbucks and grabbed breakfast for everyone. I can say with total conviction that the Starbucks at the corner of Lake Street and Michigan Avenue is the best Starbucks I have ever been in. Forget the food…that’s the same everywhere, but the employees were AMAZING. Pablo (at the register) greeted me by name on my second visit. He taught me how to stack a ton of food in a big bag to get it back home, and every time a regular came in, it was like Norm coming into Cheers. If you are anywhere near that Starbucks, it is worth a visit.

After breakfast, we were off to our boat ride Architectural Tour with Chicago Architecture Center aboard Chicago’s First Lady. This outfit is a nonprofit organization, and the person giving the tour is a volunteer docent who keeps an incredible number of facts in her head. I wish I could remember any of them, but three days later I can only come up with a few. But here are the pics and why I took them in the captions, which you can see by clicking on any photo.

After our architectural tour, we had a nice lunch right next door to our building at the Elephant and Castle British Tavern. The food was OK, but the waiter was great. He suggested that since we had already sampled two of Chicago’s iconic food and drink items, we should try a third…a shot of Malört. Malört is a bitter, wormwood-based herbal liqueur. Drinking a shot of Malört is widely considered a rite of passage for visitors and a badge of honor among Chicago locals. We tried it, and we passed. It wasn’t terrible. Kind of a cross between turpentine and shellac ?.

After lunch, we headed to one of the highlights of our trip: a visit to the newly opened Obama Presidential Center in South Chicago. It is an amazing place. If you go, get tickets well in advance. They are currently sold out through the end of the year. It is well worth the trip. The photos below will show you why, but suffice it to say, it proved what I have always believed. He may not have been our greatest president, but he was the greatest man ever to be president. No scandals, no affairs. He was never president just to benefit anyone but the people of the United States of America. Touring the center also made us sad to see how far the government of this country has sunk in less than 20 years. It is disgusting. If you can, visit here.

Our tickets were for 2:45, and we didn’t leave until almost 4:30. By the time we got back to the Airbnb, we had just enough time for a quick nap before heading out to dinner at a restaurant I found on Eater. If you are not familiar with Eater, check them out. There is one for just about every city or region in the world, with great recommendations that fit my taste exactly. Go there and type in where you live, and see if their picks match places you have been. I usually do well when following their advice. We found the Frontera Grille on that same list, where we ate the night before.

That night, we were eating at Rose Mary. It is a Croatian-Italian restaurant that serves food family-style. We were seated right next to the HUGE demonstration kitchen, which I loved. I could watch the chefs work and maybe pick up some techniques. Our server, Illyna, was superb, and her station was right next to where we were sitting, so we could talk to her and ask for recommendations. We ordered cocktails, and everyone liked theirs. I am not drinking much on this trip after my cardiac episode in June, so I stuck to the mocktails. They have one there with Luxardo syrup and Ginger Beer that I will be making at home…I promise.

The meal itself was amazing. Since it was served family-style and Illyna advised us to order six dishes for four, we each ordered one, and then each couple ordered one. Cathy decided on their Grilled Summer Squash. It was made with parmesan fonduta, beef fat, pickled summer squash and basil. I thought, “Well, I won’t want much of that.” When it came, I tried one bite and about passed out. It was that amazing. I have never tasted anything like it. It was the best thing I ate all night, and that is saying a WHOLE lot.

They served each plate separately, giving us time to digest and enjoy it. Second up was the risotto. Maybe the best risotto I have ever eaten. It featured veal breast, Parmigiano, chicken thigh, and tomato. This was followed by a pasta dish called Mafaldine with lamb ragu d'abruzzo, cacio and cavallo. Delish, but only a 9 out of 10.

We had a hard time picking our fourth dish until the two very nice women next to us had one arrive at their table that looked beyond belief. We asked them what it was and were told it was branzino. This worked out because we hadn’t ordered any fish yet. They make their branzino with a soppressata vinaigrette, artichokes, and grilled lemon. This one got a solid 10 as well.

Mike had started ordering the Pork Ribs Campanella. The ribs have Calabrian chile agrodolce, walnuts, and cabbage & yogurt relish on top. Another solid 10. I forgot to mention that early on (with the squash), we decided we had to have bread to sop up any leftover sauces, and I can guarantee you that no plate we sent back needed to be washed too well.

While we were finishing the third or fourth dish, I mentioned that they had octopus on the menu and that, since it’s my favorite food and every dish had been superb, I probably should try it. Cathy agreed to split it with me, and we ordered it. I almost wish we hadn’t. It’s as good—a solid 8—but not at the level of everything else that night.

No matter that, it was an amazing dining experience from start to finish. It was so good that I have to come up with another test that’s above the Steve Test. For those of you who are new here, my brother Steve came up with a test for a restaurant… if you had that restaurant at home, would you go there? If the answer is yes, it passes the Steve Test. Well, now comes the Jim Test. If the restaurant is so good that you would plan a trip back to that city just to eat there again? For Rose Mary, my answer would be yes. Or maybe I should also say that it means if you visited that city again, you HAVE to go there.

I don't want to make decisions about what I'm eating or wearing. Because I have too many other decisions to make.   —Barack Obama

Day Two in Chicago—walk, breakfast, TOUR, hotdog, TOUR, dinner

by | Sep 29, 2026 | Food Experiences, Photography

Yes, it does seem like all we do is eat, doesn't it? Well, our first full day in the Windy City (we found out it isn't named that because it is windy here; it has to do with politicians making a lot of wind with their speeches) was an all-tour day. We had booked a Chicago Overview Tour with Johanna through Tours by Locals, a company I have highly recommended for quite a while now. Their guides never disappoint. Johanna was no exception. But more about that later. But first, my early morning walk.

The absolute best thing about our Airbnb is its location. For visitors, the city center is Millennium Park. It is the one with the big BEAN art installation in the middle, and it is next door to the Chicago Art Institute. The park has so much more to see, and right now I am looking out the window of our 23rd-story Airbnb and staring directly at the park. That meant there were lots of places to walk to when I wanted to take early-morning photos. So I was up and out at 5:30 to make sure I got my full golden hour and was there for the sunrise at 6:34 am. Here are the photos from that walk.

 

When Kathleen and I were here in 2013 to visit my brother John, we went to breakfast at Wildberry and loved it. Since then, they have added a really nice, rather large patio with lots of tables. And believe it or not, in late September we were really happy to be seated out there. It was beautiful and warm. Our breakfast was also pretty much AMAZING. Check out the pics and my captions, and try not to get hungry.

After breakfast, we were headed out for our tour with Johanna. She got held up on the other side of a motorcade for the leader of the free world (snort), who was in town to present an award at a golf tournament. I am not going to get political here, but seriously…

Johanna finally arrived, and we headed out. Our day was full of quick stops where we would jump out, take photos, jump back in, and head somewhere else. We saw bridges, churches, skyscrapers, neighborhoods, great views, and so much more. And all along the way, Johanna kept us fully informed about what we were seeing, as well as Chicago's history and geography. She is a true local, having grown up here, and she knew a lot of information. We went to a bunch of places, and these are the before-lunch shots.

Last night we had our first iconic Chicago dish—deep dish pizza. Today our lunch would be the second iconic Chicago food, a Chicago hot dog. Before we left, we knew we wanted to try one, but all we knew about them was that you NEVER asked for ketchup on them. EVER! And I will admit that when it comes to hot dogs, I am a ketchup guy. But once I tried the Chicago dog, I may never go back. If you are unfamiliar with a traditional Chicago hot dog, it has an all-beef dog with tomatoes, pickle relish, mustard, a pickle spear, and small piquant peppers, all on a poppy seed bun. DELICIOUS! See the pics. We loved them. One made a super lunch, since we had that big breakfast and were going out later that night.

After lunch, we were back in the car for the second half of our tour. See the afternoon photos below. Around 4:00 pm, Johanna dropped us off at our Airbnb, and we said a fond farewell. I would recommend her to anyone for a fact-filled, fun day. Photos from the afternoon are below.

To finish up our tour, some scenic shots from different spots. This one near the Aquarium was a super view of the Chicago skyline.

We were back at the AirBnB for about 90 minutes, and then we had reservations at Frontera Grill, one of Ricky Bayless’ Mexican restaurants here in Chicago. We had been to his “higher-end” place (Topolobampo) when we were here in 2013, and although it has a Michelin star, we weren’t impressed. I don’t understand the whole “foam as food” thing. It was four people for more than $400 (in 2013!!!), and we all left hungry. Last night at Frontera was not like that. The Eater website (where I find a lot of restaurant recommendations) said it was “not the pretentious food you would find at Topolobampo.” Thank the gods, it wasn’t. It was a delicious meal.

And that was enough for our day. We were all wiped out, and we had an early meeting with an architectural tour the next morning.

“It’s the finest hot dog on the planet, the one they make in Chicago. I said it, and I meant it!” —Anthony Bourdain

Day One in Chicago…it’s all about the Deep Dish

by | Sep 27, 2026 | Uncategorized

I know, that's what everyone says when they are on vacation but there is something about having a great day that just makes a vacation day special. In fact, so far this has been one great trip.

Kathleen and I had booked my favorite transfer company, Welcome Pickups, to get us to the airport. Our driver kept in contact before we left, and we asked if we could be picked up a little early because the main freeway to the airport was closed for the weekend and we might run into traffic. He was happy to oblige, arrived half an hour early, and then got us to the airport right on time. Our Alaska Air flight was on time (we were kind of worried because it had been more than 90 minutes late the day before), and we were at the gate with plenty of time to spare. Enough time for Kathleen to make a new friend with another woman who had come from check-in via wheelchair…or cool scooter.

One thing that kind of ticked me off (first-world problem coming) was that even though we were flying Alaska in first class, we didn't have access to the first-class lounge. Alaska Air only gives you that if your flight is more than 3,000 miles. Since ours was just under 2,000, we did not qualify. And a beautiful, brand-new Alaska lounge sat just above our heads on the next floor up. Wish we could have seen it.

But no other complaints about the flight. We took off on time, had a nice lunch, arrived early, were off early, had our bags quickly and found our second Welcome Pickups driver of the day, who whisked us into downtown (took about an hour)to our AirBnB, where we found Mike and Cathy waiting for us.

It’s a pretty decent AirBnB. Some folks have told us they have had no luck with vacation rentals, but this is about our 30th, and we have never had a real problem with any of them. This one is excellent. We are on the 23rd floor with an amazing view of downtown Chicago. We are right next to the EL train but being up 23 floors helps. That's the living room up at the top of this page. If you want to see the rest of the photos of the place, check out the AirBnB listing by clicking here.

We have pretty much planned all our eating for this trip… start to finish. We want to try all the foods Chicago is famous for, so last night, after we got in and hooked up with Mike and Cathy, all four of us headed over to Giordano’s (recommended to me by a Trilogy Travel Club member from Chicago) for our first taste of Chicago deep-dish pizza. It was amazing! See the pics below. We ordered two smalls for four of us and could have done with just one. We both ended up taking half a pizza out into the world after dinner. I would like to say I took it back to the AirBnB, but with all the other food experiences we had coming up, it just didn’t make sense. But on the other hand, they were spendy pizzas, so we took them with us.

Just outside the restaurant, I ran into a homeless man who asked if he could maybe have a piece. I handed him the entire box, which had half a pizza in it. He was VERY grateful. Mike took his half back to the building we were staying in for the concierge, who had been letting us in and out. He too was very grateful. We loved the pizza, but there was just too much of it. I also need to mention that when you go, they bake the pie fresh, so it takes 45 minutes from the time your order goes in until you get the pizza. Thankfully, they had some great salads on the menu as well.

After dinner, it was a quick walk back to the Airbnb for a good night's sleep before our first full day in Chicago. More tomorrow. In the meantime, enjoy the pizza pics.

"You better cut the pizza in four pieces because I'm not hungry enough to eat six."  —Yogi Berra