Jamaica, Mon. Irie…..

Bob Madden responds to the crowd, egging him on!

For the last four years prior to this trip, the morning show that I am fortunate to be a “cast member” of out of Milwaukee, WI – “Bob and Brian In The Morning” (Complicated title, eh? Makes you really wonder what the show is all about.) – has led a group of about 200 listeners to Cancun/Riviera Maya for a week of middle aged drinking and a desperate attempt to turn the clock back on father time.

This year, we were sent to Jamaica instead, because of increasing drug cartel violence in the Quintana Roo state of Mexico where all the Yucatan peninsula resorts are located. Apparently the station’s parent company said insurance on the trip was going to be through the roof. Mexico, sadly, was closed.

And I don’t think we’re going back anytime soon. Something about one tourist ferry boat getting blown up, and another one being found wired up and ready to go ka-boom will do that kind of thing. Pity. I liked Mexico. But I think I’ll warm to Jamaica if it becomes our home for the next four years (fingers crossed!)

Not that Jamaica isn’t dicey in it’s own ways. In fact, some gang-bangers started shooting up downtown tourist mecca Montego Bay at the start of 2018, and so they put in a state of emergency which featured roadside checkpoints designed to catch the bad guys driving around the island (I was dubious of their effectiveness, but hey, what do I know?)

I do know this: the Jamaican people who work the resorts, could NOT be any warmer, nicer, or damn funnier. Man, what a people. And look, I know. It’s a resort. It’s not like every Jamaican would greet you the same way if you decided to go walking around Kingston on your own. (In fact, I was told that was akin to a suicide stunt, but what do I know?) Still, to call Jamaicans warm and joyful, is an understatement. The men. The women. The old dudes driving our buses. All of them. The best.

And it’s not like the Mexicans were rude. Hardly. They too were excellent at the resorts. But the Jamaicans cracked me up. All day long.

The trip was, as expected, awesome. I’ve said it before, and I’ll say it again: you get to be my age (49) or older, and you have to start reminding yourself every chance you get: “THIS…. is as YOUNG… as I am EVER, going, to be, again. So you better start acting like it!”

The group (most of us, at least) gather one last time on “The Staircase of Death” in the lobby.

The people who go on this trip, are the ones who make it so special. You can book any number of great resorts in the Carribean on your own, get a great price, have great weather, be with someone you love dearly…. but you can’t be part of what is like a drunken family reunion for an entire week. In fact, we hooked into a couple from Great Britain, who stumbled by the radio show’s beachside set location one morning. He was instantly smitten with Bob and Brian and the show. “Those chaps are…. SMASHING!” the husband said to everybody who would listen. By the end of the week, he had a Packers hat and jersey, and about 50 invites to come to Lambeau this season.

I’m lucky to be a part of it. Sure, I’ve been doing a sports segment with them for 24 years now, which I started back in my single days living in Northbrook, Illinois working for the “One On One Sports Radio Network.” So they wouldn’t think of NOT inviting me. But still. I take nothing for granted. And I try to jam in as much of everything as I can with the group during the week, and somehow keep up on the drinking (it’s hopeless, they are basically professionals!).

So with that said, here’s a recap and rating on Jamaica vs. Mexico.

Flying into Montego Bay was a joy compared to Cancun. Much smaller, much easier to get through customs. That said, if you are going to the other side of the island’s resorts, you’ll be on a bus for 2 more hours. Not ideal. Our place (Iberostar Rose Hall Suites) was only 15 minutes. Easy peasy.

The pool/beach set-up was perfect. Easy walking distance for whatever you prefer, but not jammed in too close. The resort was NOT adults only (which many of your peeps harumphed at) but the kid factor was minimal. Maybe 5%. Pool and beach chairs were ample. No need to wake up at dawn to claim one. The reefs around Jamaica made for a safe, and gentle ocean swim. Drink service (all inclusive) was good and friendly.

The resort’s activity staff (or “hype crew” as I call them) were hilarious. “Peaches” (his nickname) held court with us one afternoon poolside explaining everything we needed to know about his native land. He also rode the inflatable bull with us, did cannonballs with our Go-Pros while claiming he can’t swim, and joined in the footrace on the beach at the end of the week (as did 4 other Jamaican staffers. They finished 1-5. Shocker!)

The buffet food at our section of the resort was EXCELLENT. Much better than I had expected. Although there was a “lower-tier” part of the Iberostar we had access too, where you could tell they got a slightly lower cut of grub. The reservation dining was just “meh.” I said it was simply a buffet you had to wait for at the table. No big deal when you were with friends and having drinks.

I missed a catamaran trip where a bunch of our people went snorkeling. The next day we went to a Margaritaville atop the water in Montego Bay. It was shockingly well run, and getting food and drinks took very little time. The main attraction was the massive 3-story waterslide, welded to the side of the restaurant’s edifice above the ocean. It looked like it was ready to rust off and crumble into the ocean at any moment. But again, what do I know? A bunch of us swam out to some giant trampolines in the water, and pretended we weren’t exhausted by the modest exercise. I tried – and failed badly – to climb the inflatable iceberg. Several of our group did however. It’s my mission next year, to conquer it.

El Baldo comes shooting out of the slide like an ICBM launched from a submarine!

Speaking of next year, if we end up in Jamaica I will certainly re-visit the “World Famous” Rick’s Cafe in Negril. Oh man, you have to see it to believe it. The most spectacular cliffside amphitheater where any dumbass tourist can jump from 25 or 35 feet off a cliff into the crystal blue waters. A full service restaurant, bar, and music stage. Sunsets off the western side of the island that make your head melt they are so lovely. It’s become a bit Wallyworld now, due to tourist poplularity, but I didn’t feel like it had been ruined – yet. Give it 10 more years.

The gals came ready to drink, and jump. But not quite in that order!

I jumped off the 25 foot ledge, and then promptly chickened out on the top-shelf jump. What a pussy, AMIRITE? Of course Bob had done such a good job of painting a picture of me getting paralyzed and “going home in your new wheelchair for life!” prior to our bus ride over there, and the warning signs make no pretense about the fact that people DO get hurt there (if not all the time, then certainly more than “rarely”) that I just couldn’t get my mind right. And it was stupid, because all you had to do was just step off the damn thing. A platform of 35 feet isn’t really THAT high anyway for a cliff jump, feet first. There’s stairs and a handrail, and a level textured surface to stand on. Simple. Old ladies and kids were doing it. I choked. Since my first jump didn’t quite score a perfect 10 (I leaned back a bit much before impact) I was spooked about my natural athletic instincts to fall straight down in the water. And since I was hell bent on getting my jump on camera with my GoPro in hand, I knew I would be pre-occupied with THE SHOT and not the landing. Before you know it, I was questioning whether my wet bare feet might somehow slip on launch. I seriously just got the yips, on what was a 6-inch putt. I picked up the ball and put it in my pocket. I’ve got something to look forward to next time.

I played golf at a place called “Cinnamon Hill” less than 3 miles from our hotel. It was fun, and the layout was wild. It had a lot of par-5’s and par-3’s and somehow I played great and shot 74. The conditions were not great, but not enough to actually complain about (“…it’s Jamaica, mon!”) The greens were slow, but puttable. Had they been much faster, some of the more severely canted complexes on the back-nine would have bordered on unplayable. The BEST part of the round – and I would have never expected it – was the local Jamaican forecaddies you were required to take. I’m not lying when I say they KNEW the game, could start clubbing you accurately by the 3rd hole, and made great reads on the greens. Best of all, they were funny and INTO IT the entire round! My guy would once every 4 or 5 holes bellow out a “WHAAAAAT!” whenever somebody hit a truly superior shot. And he knew which ones deserved it. I somehow lofted a feathery 60 degree flop shot over a greenside bunker to a tight pin on #8 to about a foot…. “WHAAAAT!” Classic. The other caddy was a woman named Carrie. She too knew exactly what the game was all about. And she was rooting hard for everybody’s ball to the bitter end. Best caddy experience I’ve ever had playing golf. I kid you not. In Jamaica.

Carrie the Caddie. Don’t let the nails fool ya! She could read greens like a fortune teller!

I was going to play the other course which is well known around there called the “White Witch” but passed to go to Rick’s Cafe that day. I was told it was similar, but maybe a bit more dramatic. Jamaica is not much of a golf destination, but it did the trick for me at least for one day.

I was able to get my Mavic Pro drone in the air a few times on the trip, but the resort security was pretty quick to shut me down two of the three times I launched. From what I understand, non-commercial drone usage in Jamaica is no big deal, but the resorts I am sure clamp down for liability purposes. I was able to launch inconspicuously from a large flat balcony above the main lobby one still morning. Once airborne at that early hour, I sat down in a leather chair and flew at will all up and down the coastline. Even if the beach patrol could see the drone, they had no way of finding me. I brought it back in after about 20 minutes, and had it packed and folded in under 60 seconds in a small sling bag. The Mavic did well in quite windy conditions. As good as the full-sized Phantom line is from DJI, I still think the smaller size is king. My Mavic was packed in my Sony camera bag along with my A6300, two lenses, a GoPro and the Sony RX100 V. I desperately wanted to fly it at Rick’s Cafe, but the sign at the from explicitly said “NO Drones.” Still, somebody on a nearby yacht launched a DJI Spark, and I am sure got some sweet footage. They can only control so much.

Speaking of “spark”…. let’s have a frank talk about ganja, mon. Geezuz, the good folks of Jamaica would offer it to you just about everywhere we went. Technically, it’s still illegal in Jamaica but almost never policed, and the fines are literally like $3 if you get caught. I said to our group that it was too bad I’ve never smoked ANYTHING in my life because if you are into getting high, Jamaica is a weed-head paradise, I would imagine. (Remember, I’m a sissy! See the diving story, above!) As for the quality of the product you get down there, I have no idea. Ask your friendly local rastafarian.

Thankfully, we had a group of almost 200 Bob and Brian listeners (and friends) ranging in age from the late 20’s to the late 60’s, and we brought everybody home safely (although one guy burned his ankles so badly on Day One, that he got puss blisters the size of mini-hot-dogs.) I say this not to be snarky, but because if this trip continues long enough into the future, with as many hard-partying old dudes as we bring each year, chances are….

Tommy the jeweler jumps the bull, and hangs on for dear life!

Our bus driver to one excursion dropped us off at the boat dock to go swim in the luminescent bay (very cool) and proceeded straight to the bar while we were gone. When got back on the bus, it absolutely reeked of ganja. Then as we drove home, he made aggressive passes while frantically thumbing through his fanny pack of Bob Marley CD’s because he felt he OWED it to us to play “the good shit.” Thankfully, the ride was uneventful. But it wasn’t coming home from Rick’s. About a mile backup stopped us dead about 10 minutes from our hotel. As we approached the cluster of police lights and ambulances, we saw one of the worst 4 or 5 car wrecks you could imagine. And yeah, right there, in plain sight under a car that looked like it had been dropped from a helicopter, was a dead man. No sheet. No police telling people to back up and get away. About 15-20 motorists who had pulled over and got out of their cars to… gawk.

All in all, I highly recommend Jamaica to anybody who hasn’t been. And a big thanks to the entire Bob and Brian show for bringing me, and Colleen at Fox World Travel in Wisconsin for being the most dutiful and diligent den mother a monster group like this could ever have. It would be my dream to get something like together for my 980 listeners here in D.C.

After all, life is short and unpredictable. And this is as young, as we are ever going to be again.


About the Author

Steve Czaban is a 25 year sports radio veteran, who hosts an afternoon drive show in Washington D.C. He also appears on "Bob and Brian" in Milwaukee. "Czabe" also writes and edits his own commentaries for www.czabe.com and other on-line and print publications. He can be reached at czabe@yahoo.com.

Author Archive Page


  1. Absolutely, positively, the best vacation we’ve ever been on! The pictures don’t do it justice…imagine the pictures/videos that CAN’T be posted!
    Many thanks to B&B, Czabe, Carrie, Eric, Colleen from Fox World Travel, Iberostar, all the ‘Benders’ who were so welcoming, and everyone else for a truly amazing vacation!

    Already can’t wait for next year to do it all over again. It’ll take me the full year just to recharge for another run though!

  2. Definitely the Best Jamaica trip I have been on so far! Bob, Brian, Carrie, Eric and Czabe were so nice and welcoming along with everyone else on the group!!
    Thanks for such great laughs memories !!

  3. So in a rare bit of fate my wife and I shared the plane with the Bob and Brian group as we had planned our Jamaican vacation to Negril completely separate of the B&B group and were completely surprised on departure Saturday to find a group of 200 waiting to check in at the Airport. The next thing we heard was “it’s all good Bob’s here” and I’m thinking “Bob…Villa?” We were quickly informed of the event and were happy to share our plane with a really nice group of people on both the way down and back. Everything Czabe says is accurate about Jamaica…they are a very nice people and everything was wonderful…the only comment I would add is that we stayed in Negril which is about a 1.5 hour trip but it really isn’t bad as the trip is very scenic and follows the ocean for a good part and Negril easily has the best beach in Jamaica.

  4. What a fantastic vacation. Thanks for being part of it and remembering us after 3 years off. How awesome that you personally said goodbye to each and every person as we got in the bus to leave. Class act.

    Dan and Donna

Post a Comment

Your email address will not be published. Required fields are marked *