What it’s like on the Jolley Trolley’s ‘World’s Largest Brew Crawl’

In Tampa Bay, a few maxims ring universally true:

The denizens of this region are wedded to cars. Despite occasional policy efforts to bolster mass transit, the concept remains a hologram bathed in a hopeful, opalescent light, always just out of reach.

Pirates help.

So does alcohol.

And so, I found myself plopped in the Venn diagram center of Floridian truisms, riding an antique trolley while seated next to a handsy plastic skeleton with an eye patch. Our destination? Lots and lots of bars. BaaAARRRRsss, if you will.

The folks at the Clearwater Jolley Trolley invited me on the World’s Largest Brew Crawl, a pirate-themed tour of 19 drinky businesses spanning Clearwater Beach to Tarpon Springs. The tour runs through the end of May, when the purveyors will assess how it’s going. I am one of the “how’s it going?” people, and I will tell you.

First, how do they know it’s the world’s largest? They have not found anything larger, a spokesperson said. Also, it’s fun to say. This is an acceptable answer to me. Greater hunches have been made under grand jury testimony, and this is not that serious.

I brought my husband, because going on a bar crawl alone is a cry for help. Musician Chris Tracy, on board for a cross-promotion with the Ukulele Fest in Clearwater, accessed my truth and started strumming the songs of Jewel and Amy Winehouse. Our driver, chatty Jenna Christenson, promised she found it fun to ferry tipsy folks around North Pinellas. We set off in the sagging sun to the tune of “Who Will Save Your Soul.”

We love to party rock, don’t we, locals? Take the Tampa Pirate Water Taxi, for example, or the Cross-Bay Ferry with its beer and wine galore. These jovial group rides are less work commute and more tools to soften the cringe of our region’s M.C. Escher traffic patterns. Picture, please, the hellscape of sitting in gridlock on the bridge to Clearwater Beach, grumpy spouse wearing board shorts in the passenger seat.

“It’s another thing when you’ve got an open-air trolley and a big beer and some music playing and you’re sitting up high above where the traffic is,” said Jolley Trolley CEO Mike Helmstetter, who would like to see ridership grow on this particular jaunt.

The bar crawl fits into the Jolley Trolley’s amusement milieu, which includes haunted ghost tours and a new historical sightseeing adventure. The nonprofit subcontracts with the Pinellas Suncoast Transit Authority, reserving 14 of 36 trolleys for the public to get around; the other 22 are for tours, parades or private rentals. We’ve all seen the cute trolley bridesmaid photos.

Our 38-foot vessel of destiny, decorated with treasure chests, skulls and fishing nets, was part of a passel of vehicles the company purchased from shuttered Lolly the Trolley in Cleveland. It is a beautiful specimen under the pirate ornaments, flush with carved wood seats and red wrought iron. Another decidedly less swashbuckling trolley acts as backup.

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Wristbands are $20, good for riding all weekend, Friday, Saturday and Sunday, with discounts at most stops. You can drink on board and bring beer, but please don’t make Jenna babysit your Yeti while you wander off.

We boarded at 7venth Sun Brewery in Dunedin and, clutching a printout of the tour schedule like nerds, stepped off in Ozona. The next pickup was in three hours, which seemed right for a drink and dinner. Jenna, blessedly, gave me her cell number.

We were the only ones on our trolley and strolled into Ozona Brewing Company, where our wristbands meant BOGO beers. Soon, a second trolley pulled up and let off 25 cackling adult birthday partiers in Hawaiian shirts and sun visors. The bartender muttered something unprintable.

After consuming a mound of fried clam strips at Molly Goodhead’s, we had more time to burn until pickup, so we browsed whimsical salt and pepper shakers at Antiques & Uniques. Then we had ice cream at Ozona Pizza. Then, we ... leaned against the post office.

Our trolley was 40 minutes late. I called Jenna, who said the backup trolley was stuck on the bridge leaving Clearwater Beach. This is no shade to utterly adorable Ozona, but I think even Ozona residents would agree we exhausted most available activities. The downtown is three blocks long!

At last, the TROLLEY CAME. We ran for it like feral cats and headed north to Tarpon Springs, our good moods creeping back to life. A couple of lovers, several sheets to the wind and canoodling heavily, rode a few seats up dressed like, yep, pirates.

We decided to throw axes at Stumpy’s Hatchet House, a task harder than it looks and demoralizing in every way. I could never survive in the woods. We arranged for Jenna to pick us up at Brighter Days Brewing across the street at the end of the night. She drove us through downtown Palm Harbor bumping “Sweet Dreams (Are Made of This),” a real celebrity moment. She talked to us about Keto recipes and her Easter plans and dropped us off at a trolley stop nearest our house. We were utterly pirated out and had a full day’s travel remaining on our wristbands.

Lessons learned

• It turns out we could have used our wristbands to get on any old Jolley Trolley, bug out of Ozona and hook back up with the pirate mobile later. Vital information, take note!

• This is really a hop-on-hop-off tour, not a linger-and-dine tour. Ride with a group of your tackiest besties and stay close to the trolley. The driver waits for 10 minutes at each stop while riders head inside for refills.

• Pace yourself, ye blimey drunks. Spread the ride out over the weekend, lest you consume 19 drinks in one night and die. No one wants that, especially not the Jolley Trolley. We had the benefit of living on the route, but otherwise, planning for an end-of-journey designated driver is a must.

• The trolley drivers are amenable to hijinks. Truly, they will blast whatever terrible music your heart desires and lead a chant of “Sweet Caroline,” all so you have a good time. Tip them! Don’t be That Guy! They get a lot of That Guy.

• Did we have fun? Ultimately, yes, even with a few seafaring kinks. Using public transport, even in its silliest forms, is a valuable way to train that atrophying community muscle that keeps us locked behind the wheel. We can do it! Tampa Bay, we can leave the car home and journey with others to our final destination, where I assure you, a cold beer awaits.

If you go

The Jolley Trolley’s World’s Largest Brew Crawl runs weekends through the end of May, taking riders to the following locations: 3 Daughters Brewing, Clearwater Brewing, Fenway Hotel, Stirling Wine, Caledonia Brewing, Soggy Bottom Brewing, Honu Tiki, HOB Brewing, House of Beer Dunedin, 7venth Sun Brewing, Beach Island Brewing, Ozona Brewing, Stilt House Brewery, Smugglers Island, Sponge City Brewing, Stumpy’s Hatchet House, Brighter Days Brewing, Tarpon Springs Distillery and 5 Branches Brewing. Wristbands are $20 at clearwaterjolleytrolley.com.

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