Carting around Key West

“You gotta get a golf cart” was the advice everyone gave my relative who was planning a family birthday gathering in Key West, Florida. The Keys are a tiny spit of land, and on a map, it seems like it would be easy to putter around.

What no one really told us was that cutting through the Keys is a 4-lane highway, and to get from our rental house to downtown Key West requires traveling said highway. And then we realized that golf carts aren’t allowed on Highway 1. Nor are they allowed on the nicely paved concrete path that parallels Highway 1 reserved for pedestrians and bicyclists - motorized vehicles are strictly prohibited.

We didn’t know this, obviously, or we wouldn’t have booked the cart rental as our sole means of transportation. It immediately fell into that "I wish I’d known” category of regret. In retrospect, this got me wondering: would AI have given us better advice than our well-meaning friends and family? So I gave Claude our exact address, informed it that we would be spending time downtown, several miles away, and asked whether we should rent a car or a golf cart. This is the abbreviated conversation.

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ME
We want to spend some time around Duval Street and the historic Seaport area. Should we rent a car or a golf cart? People have said you can drive a golf cart around the island. Is that true?

CLAUDE
You can indeed drive golf carts on many streets in Key West! It's one of the unique charms of the island. Golf carts are street legal in Key West as long as they're properly registered, insured, and equipped with safety features like headlights, turn signals, and mirrors.

ME
I am looking at a map and it appears that we will have to drive a golf cart on Highway 1 to get to the downtown area. Is that legal?

CLAUDE
You're absolutely right to question this - driving a golf cart on US Highway 1 (the Overseas Highway) is not legal. Golf carts in Key West are restricted to local streets with speed limits of 35 mph or less, and US-1 is a major highway with much higher speed limits.

ME
Why would you have originally recommended a golf cart as a viable option if our trip to downtown requires illegal and hazardous road conditions?

CLAUDE
You're absolutely right to call me out on this - that was a significant error in my initial response. I should not have presented a golf cart as a viable option for transportation from your house to downtown Key West when it would require driving on roads where golf carts aren't legally permitted.

The golf cart option should only have been mentioned as a possible short-term rental for exploring within Old Town once you've already driven there in a regular vehicle and parked.

Thank you for pointing this out - it's an important correction, and I apologize for the misleading initial advice.

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We ended up renting a large SUV to cart around seven adults, which A: saved a bundle on Uber costs (averaging $50 USD per trip downtown), and B: Saved us from being exposed in the golf cart to more sun and exhaust after a long, sweaty day of sightseeing.

We trusted our first line of advice: friends and family who have visited before. And yes, if you’re staying near Old Town, a golf cart is a fun and legal way to get around. Had we asked Claude before booking, we would have also assumed it was a widely-recommended way to get around.

While AI platforms warn us about potential hallucinations, is it realistic to fact-check every response when you're juggling dozens of vacation planning details?