Private tour in St petersburg Jimbo C

Clearwater Beach Tropical Bites & Quirky History Walking Tour — with Trivia, Treats & Toasts!

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Hours icon 3 hours 30 minutes
Walking
Private tour for 1-10 people
Your party size

1

Tour date
Start time
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 3 hours 30 minutes
Walking
Private tour for 1-10 people
Your party size

1

View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later

Jimbo C.

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Who is ‘Jimbo’—and why should he be your tour guide?! Well... maybe you shouldn't pick me. There are some incredible guides out there. But—if you’re into guides who are wildly passionate, genuinely caring, a little quirky, and absolutely committed to creating unforgettable, joy-filled adventures—then I might just be your guy. I love what I do so much I’d honestly do it for free. (Let’s keep that between us though... my accountant already has concerns.) I’ve always been drawn to tropical escapes, warm beaches, incredible food & drink and amazing times. Growing up in Chicago—a city bursting with culinary greatness—I developed a sharp palate, a big appetite, and a deep appreciation for diverse cultures and bold flavors. But even as I navigated the Windy City’s food scene, my heart was somewhere warmer. After years of childhood pilgrimages to Clearwater Beach (and a lifelong, often painful, devotion to the Miami Dolphins), I knew the tropics were calling. In 2004, I answered—and made Florida my home. Most recently, I left behind a 25-year tech sales career to follow my heart into something far more fulfilling: crafting amazing, impactful experiences for amazing people. Every single day, I get to meet curious, wonderful guests like you... share great bites and sips, swap stories, dive into quirky local history, and laugh until our cheeks hurt. My tours blend Florida’s tropical charm, rich history, vibrant flavours, and a dash of competitive fun—with trivia contests, secret prizes, and an exclusive “celebration chant” of good times and gratitude. I pour my heart into every experience, making sure it feels personal, memorable, and full of joy. And if you don’t see the perfect tour? Let’s dream one up together—Your vision, my passion! Creating lifelong memories for people means everything to me. Unbelievably excited to meet you and your guests on one of my tour soon -Cheers! 'Jimbo'

Have a question or want to customize this tour? Message Jimbo C.

Overview of your St Petersburg tour

This is a full-on Tiki-Tastic, ridiculously fun, high-energy, bold Trivia, belly laughs & beach bites adventure through one of the country's most dazzling coastal destinations: Clearwater Beach - ranked #1 by USA Today! Prepare to embark on a gastronomic journey as vibrant as the beach itself. Think freshly caught local fish, authentic regional food & ice-cold beachy cocktails. Between bites, I'll share Clearwater Beach’s top 10 quirkiest local history tidbits—and we’ll even make a pit stop at local legend Hulk Hogan's statue for a photo op. I encourage you to compete in an epic foodie trivia challenge for a chance at a mystery prize & eternal glory (or at least bragging rights). I'll also teach you our secret celebratory chant of good vibes & gratitude—only revealed to tour legends! This is more than a food tour—it’s a bonding experience for couples, friends or family, a local adventure & a sweet slice of beachside life. Bring your appetite, a curious mind & your biggest smile—can't wait to meet you!

Your St Petersburg tour itinerary

-Let the fun begin at Papaya Street Plaza from where we'll proceed with delicious eats, quirky local history, a magical foodie toast, and a trivia contest with a mystery prize on the line! -We'll proceed with a local flavour kickoff, tasting fresh Gulf seafood bites. -We'll then swing by a Clearwater Beach must-see for a photo op with Clearwater's local celebrity, the legendary Hulk Hogan (statue & shop). -Next, we'll keep the flavour train rolling with a second savoury seafood appetizer at another local favourite! -Afterwards, it'll be time for a mystery delicacy! This uniquely local treat will surprise your taste buds and earn you some serious foodie bragging rights. -Later, we'll dig into an authentic 900-degree wood-fired margherita pizza (made with hundred-year-old yeast) & creamy vodka penne pasta made with ingredients straight from Italy! -For the grand finale, we'll finish with a tasting of handcrafted Italian gelato and battle it out in our final trivia showdown for foodie glory!

Want to customize this tour?

Tell your guide which places matter to you, skip what doesn't, and tailor the experience for your group's needs. Not finding what you want? Message your guide to build something unique.

Transport details
Type: Walking

Transportation can be provided to & from an agreed point as an optional service. I offer executive sedans, suvs, & sprinter shuttles depending on group size. Prices vary on the size of the vehicle so please contact me for a quote if you'd like to request transportation and I'll customize this tour for you.

What's included
Private Guide
Food Drinks Snacks
What's not included
Private Transportation
Public Transportation
Private Transportation With Driver
Equipment
Classes Workshop
Services
Tastings: Optional 'Adult drink package' offering the choice between a selected alcoholic drink or a tap beer at each stop.
Meeting location

Clearwater, Florida, 33767, United States

Papaya Street Plaza 438 East Shore Drive Clearwater, FL 33767 South or Next door to the Marriott Courtyard, Clearwater Beach.

Other details
Tour categories
History
Off The Beaten Path
Food And Drink
City Highlights
Tour reference number
1421797
Languages
English
Activity level
Moderate
Accessibility
Wheelchair Accessible
Kid Friendly

Frequently asked questions

Who is this private tour in Clearwater best suited for?

This private tour in Clearwater is perfect for couples, friends, or families looking for a fun and engaging experience. It's ideal for those who enjoy local food, quirky history, and a bit of friendly competition with trivia challenges. If you're looking to connect with a local guide like Jimbo C. for deeper insights into Clearwater Beach, this tour is a great choice.

What should I bring or wear?

Can this private tour in Clearwater be customized to focus on what I want to see and skip places I've already visited?

How long is the tour, and can the start time or duration be adjusted?

Where does the tour start and end?

Is transportation included?

How much walking is involved, and is it suitable for kids, seniors, or travellers with mobility concerns?

What languages is this tour offered in?

What's included in this private tour, and what should I budget for separately?

Is this a private tour? What is the maximum group size and the starting price?

AI-generated. Please confirm details with your guide

-
Hours icon 3 hours 30 minutes
Walking
Private tour for 1-10 people
Your party size

1

Tour date
Start time
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 3 hours 30 minutes
Walking
Private tour for 1-10 people
Your party size

1

Tour date
Start time
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
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