My wife and I have driven to and flown into Key West more times than I can readily count. And while they're both fine, nothing compares to the Key West Express trip we just took for a weekend getaway. The entire process, from making the reservation to grabbing Bloody Marys when we got on the boat, was super-simple. DO NOTE: If you plan to have drinks on the trip, bring cash. Once the boat gets off shore, they lose internet and can't run a credit card.
I've been around boats my entire life, but my wife hasn't and she was a bit nervous about the boat rocking. But even in the heavier seas on the way down, the boat is big enough and fast enough that she had no ireal ssues. And the view from the top deck is like something out of a Corona commercial.
When you fly into KW, the airport is on the far side of the island from Duval St/Mallory Square, and it's a $25 minimum cab ride (no Uber there yet). And having a car there can be a liability since parking can be really hard to find. But the boat dropped us right at the marina. You step out and there's Dante's on one side of you, and Caroline St on the other. We used the Paradise Porters, who delivered our bags from the boat to our hotel, and then picked them back up when we checked out on Sunday, so we were free to explore the moment we stepped off the boat. Fantastic.
ALSO NOTE: the Key West Ferry Terminal inexplicably does not have its own bar. We would've enjoyed a cocktail or two while waiting to board for the return trip, but no such luck. Next time, we'll get them in to-go cups! And next time, we will absolutely use the express again.
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