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All Aboard! Taking the Key West Trolley Tour

As many of you know, walking the streets of Key West’s Old Town is one of the most enjoyable things you can do on this tropical Florida isle. Its historic houses bring to mind the colorful wooden cottages and bungalows you find on many Caribbean islands, particularly in the Bahamas. So over the years of island runaways to Key West, I never took a Trolley or Conch Train tour. Not a single one. Why bother, I figured, when I had perfectly good guidebooks and loved to walk up and down the streets with names like Petronia, Simonton, and Caroline.

(Boarding the trolley. Photo by Zickie Allgrove.)

But this past August, my traveling companion Zickie and I finally broke down and took the Key West Trolley. It would be easy to blame the blanket-like Florida humidity and heat, which made even this Florida native go in search of some shade. But it was more than that. My attitude toward bus tours has changed: rather than see them as overly touristy, I’ve come to appreciate that touring in a motorized vehicle can give you the best overview of any destination.

(The Shell Warehouse with its tempting souvenirs. Photo by Zickie Allgrove.)

After buying our tickets, we boarded near the Shipwreck Museum and Shell Warehouse, not far from Mallory Square. Our driver and guide was a friendly, funny woman who immediately regaled us with Key West tales. She was a real local, even honking her horn once or twice at friends and neighbors as they drove by. As many times as I’d explored Key West, I’d never had a real "Conch" (Key Wester) show me around. What a difference.

You can “hop on, hop off” trolley at over a dozen stops, but for our first ride we did almost the entire loop. In fact, the Trolley eventually left Old Town to travel down Roosevelt Boulevard where we could spot the bright blue ocean. It turned around at the East Martello Fort and Museum and headed back to the Key West Old Town sights.

(Riding the trolley outside Old Town. Photo by Zickie Allgrove.)

At the Southernmost Point in the United States, Zickie got some shots of the painted buoy and we watched the long line of tourists waiting to get their pictures taken beside it. It was so hot that day we had no desire to get off the trolley and join them.

(The southernmost point. Photo by Zickie Allgrove.)

One of my favorite attractions is always the Key West Lighthouse. It's so striking against the cerulean blue island sky.

The lighthouse is just across the street from the Hemingway Home. We did hop off the trolley so we could take a guided tour of the house. Despite my love of walking, I was grateful that after exploring the Hemingway home, we could get back on a different trolley.

One observation you can't help but make as you ride through the tree-lined streets: the history of this town, from its bars to its wood-frame churches, is simply amazing. The number of structures that have been restored, or are being restored, is so impressive, particularly when you consider how challenging it is to maintain these buildings in the humid, hurricane-prone tropics.

(History on every corner of Old Town. Photo by Zickie Allgrove.)

One slight problem with taking a moving tour? Sometimes your photographs come out a little crooked:

(Typical conch cottage in Key West. Photo by Zickie Allgrove.)

But that turned out to be no big tragedy, because we had plenty of time to walk the streets later, and take steadier pictures. So, our final assessment of the Key West Trolley tour? One of the best experiences of all our trips to Key West. In fact, because our ticket was good for two days, we jumped on another trolley the next day. All the drivers we encountered were loads of fun, and all of them have their own entertaining take on a city they clearly love.

Would I ride it on our next trip down to the Conch Republic? Absolutely!

Key West Trolley Tours notes:

Save about $3 per ticket if you buy them online. To start the tour at the beginning, board at their ticket office by the Shell Warehouse and Key West Aquarium. Kids under 12 ride free. Tickets are good for two days. You can also look over their tour map online, so you can plan in advance where you'd like to get off the trolley and explore.

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