Key West is the southernmost city in the United States, and is located just a few hours south of Miami. It is a very casual and relaxing tropical town, and a very fun place to spend a few days. These tours are all excellent ones you can take to get a good overview of the island. Then, you can decide what to explore further on your own. Note that these are all land tours. Key West also has plenty of tours in and on the water that you can look into as well.
Spend just a few minutes in Key West and you will likely see either an Old Town Trolley or a Conch Tour Train passing by. These two are by far the most popular ways to tour the island, no doubt because they both allow you to hop on and off as many times as you like during the day. This is a definite advantage, since driving and parking on this small island can be very tricky.
Old Town Trolley has been around for decades, and offers similar tours in many other cities. There are 12 stops around Key West where you can get on or off, and trolleys come by very frequently. It takes you to all of the most popular spots, and the guides give both fun and useful information in a friendly and humorous way. The Old Town Trolley operates from 9 am to 4:30 pm daily, with departures at least every 30 minutes. Kids 12 and under ride for free.
Having first started back in 1958, the Conch Train continues to help visitors explore Key West. As with the Old Town Trolley, the Conch Train Tour allows you to hop on and off as many times as you like during the day. However, they only have 4 stopping points, rather than the 12 that the Old Town Trolley has. Stopping points include Front Street Depot, Station Depot, Truval Village, and Flagler Station. You can buy tickets and board or re-board at any of these 4 locations.
The second stop, Truval Village, is a great place to get off and explore the nearby attractions including the Hemingway Home, Key West Lighthouse, Southernmost Point landmark, Key West Butterfly and Nature Conservatory and all there is to see and do on upper Duval Street. The Conch Train Tour operates from 9 am to 4:30 pm daily, with departures at least every 30 minutes. Kids 12 and under ride for free.
The Key Lime Bike Company offers small group tours that are a fun and more personal way to take a guided tour of Key West. And you’ll get some good exercise too! Tours last about 2.5 hours, and include stops at popular spots such as Jimmy Buffett’s hangouts, Sloppy Joe’s, the Hemingway House, the Southernmost Point landmark, and the Key West Cemetery.
The bikes are well-maintained and comfy, you go at a leisurely pace, and the owner/guide is very friendly and knowledgeable about the area. Tours are offered daily at 10 am, and end with a complimentary piece of genuine Key Lime pie. If you prefer to tour on your own, the shop also rent bikes for the day.
If you don’t mind walking, this 1 ¼ mile tour is a good one to get an overview of the history and architecture of Key West. The tour lasts between 1 1/2 to 2 hours. From May-October, tours depart at 9:30 am daily. From November-April, tours depart daily at 10 am, 2 pm, and 4 pm. All tours depart from the Shipwreck Historeum on Whitehead Street. Children age 4 and under are free.
For something more spooky, try this 90-minute walking tour. This alternative tour gets consistently better reviews than similar ghost tours in the Keys. You’ll learn the stories behind haunted mansions and pubs, the island’s oldest graveyard, Robert the Doll (this one really freaks me out), and other mysterious sites. On several stops, you get to go inside the location. Tours depart each evening at 7 pm and 9 pm.