Old Town Trolley Tours

Member Rating 5 out of 5 by two cruisers on August 20, 2006

We bought tickets of the Old Town Trolley to tour the island. ($20/adult) We selected this one because we could get off at any stop and reboard later. We just couldn’t pass go and collect $200. Some of the tour drivers were better that others in being humorous and informative. Some got tips from us, some didn’t. We boarded at Mallory Square. We learned from our first driver that Tennessee Williams lived at the La Concha Hotel for two years while he wrote “Streetcar Named Desire”.
After lunch and a little shopping we rode to the next stop, about 3 1/2 blocks…but they were uphill. Poor excuse, Key West rises all of 5 feet above sea level. This stop is called the Bahama Village Market, just half a block up the hill is the Ernest Hemingway Home and Museum.

After our tour we reboarded the trolley. This trolley driver told us about the lighthouse across the street from the Hemingway House. We had wondered why it was sitting so far from shore. One particularly bad hurricane seriously undercut the structure, so it was decided to move it inland. This was the highest point of the island.

We proceeded on the round island tour. The next trolley stop was at Henry Flagler’s historic Grand Hotel. Since he pushed the railroad down the keys, he needed a reason for people to come on down.
We did disembark at Southernmost trolley stop. We walked to the Southernmost Point (continental) U.S.A. monument. Traffic was thick with people trying to take pictures from car windows. I pity the residents of the neighborhood. It must be nearly impossible to get in and out of driveways. There was a long line of people waiting to photograph each other in front of the monument. We spent our time walking behind the monument and looking at the Southernmost rocks and the Southernmost crabs.

Our tour guide had told us the tale of how Key West became the Conch Republic. The Federal government began a policy of searching all vehicles returning to the mainland from the keys in search of illegal aliens. That greatly effected tourism, and the daily routine of Florida citizens who live on the keys. They retaliated by seceding from the union and declaring themselves the Conch Republic. They then declared war on the USA, then immediately surrendered to the Navy base and demanded $1 billion in foreign aid and relief.

We visited the Historic Seaport and marina. We were duly impressed with the number and variety of boats lined up along the piers.

We returned to the starting point via Duval street. The guide told us that Duval street has two personalities. Lower Duval has 80 bars in a three block stretch. At least three of them are clothing-free. Upper Duval is lively, too but in a different way. This is where the fancy shops and galleries are.
We actually saw Mile Marker 0, just before we turned into the Clinton Square-Mallory Square traffic.
Old Town Trolley Tours
6631 Maloney Ave.
Key West, Florida, 33040
(305) 296-6688


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