Support Us Button Widget

Play “Would You Rather” with us, Tampa Bay

Pull this TBAY-specific game out at your next social outting.

Tampa skyline at night

Play this game with your friends as the perfect nightcap.

Photo via @trevorcreative

Table of Contents

When was the last time you played a game of “Would You Rather,” TBAY?

In case you’ve never played, here’s a quick rundown:

Step 1 — A question is posed that pitches two options. Example: “Would you rather live in the Tampa Bay area, South Florida, like Miami and the Keys, or any other city in the world?”

Step 2 — You decide what you’d rather do. No surprise here; we’re saying the 813/727.

Now that you’re a “Would You Rather” expert, let’s tap into our inner middle schoolers and play this nostalgic game featuring some of TBAY’s most iconic landmarks, qualities, and dishes.

Don’t worry, we won’t ask you anything gruesome or anxiety provoking (that’s not really our style).

Whether it’s choosing between spending time with Tampa influencer Kat Stickler or Stephen Marley or deciding if you’d rather have a lifetime supply of Jai Alai or Busch Gardens tickets, we want to know what you’d rather do.

Question one

Would you rather spend two hours playing tourist around town with social media influencer and comedian star Kat Stickler OR go behind the scenes/be on stage for any future Jannus Live concert?

  • I want to play tourist with Kat.
  • I want to ask The Backseat Lovers and Stephen Marley if I can play on stage.

Question two

Would you rather have the endurance to run the Tampa Riverwalk without stopping OR the speed to walk from the St. Pete Pier to St. Pete Beach in two minutes or less?

  • Give me endurance.
  • Give me speed.

Question three

Would you rather a Tampa Bay sports team win a major championship and drive tons of new people (both tourists and new residents) to town OR have Tom Brady come back to play for the Bucs? Bonus: OR have TBAY score an NBA team.

  • Bring on the economic boost
  • Come on, he’s the GOAT… we just need one more season.
  • Tampa Bay Ballers vs. Steph Curry and the Golden State Warriors has a nice ring to it.

Question four

Would you rather sit in rush hour traffic on Gandy with SNL superstar Kenan Thompson in your passenger seat OR wait for an hour to get a reservation at bartaco in Hyde Park on a Friday night?

  • Hold on, let me get my traffic snacks and get ready to laugh.
  • I can’t wait to walk around Hyde Park + eat some pork belly tacos.

Question five

Would you rather have unlimited Busch Gardens passes OR unlimited Jai Alai from Cigar City Brewing?

  • Iron Gwazi for life.
  • Beer me, please.

Question six

Would you rather never have to pay for parking again OR never have to look more than two minutes for parking again in Downtown Tampa, Hyde Park, or Downtown St. Pete?

  • I’ll save a buck.
  • Oh, take my money. I hate looking for parking.

Question seven

Would you rather experience TBAY 100 years ago OR 100 years in the future?

  • Please take me back.
  • Show me the future.

Record your answers here. Thanks for playing, TBAY. Is there a “Would You Rather” question about the city that you’d like to see answered? Send it our way, and we might just pose it to your fellow readers.

More from TBAYtoday
Whether you want to indulge in a lavish end of year meal or shimmy all night, we’ve got you covered.
Let us know what we should cover in Tampa + the Burg in 2025.
The pocket of Scotland and TBAY sister city is home to thousands of years of history.
Well, maybe not us directly — but TBAY and St. Pete really are the gifts that keep on giving.
As Tampa Bay continues to grow, we’re keeping an eye on upcoming developments and recently-opened businesses.
TBAYtoday readers shared which local restaurants + meals they miss the most — and we think you’ll agree.
Historical markers are physical signs, plaques, and statues that commemorate a significant place or event. Where would you like to see a historical marker around Tampa Bay?
Pack your reusable shopping bags, because we’ve rounded up 12 farmers’ markets around TBAY.
Bookmark this list for when you don’t feel like cheffing it up for the holidays.
We’re checking in on where the Rays might play in 2026, the Bucs’ victorious run, and who’s playing in the ReliaQuest Bowl.