How To Enjoy Your Half-Day In Colorful Key West Port

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Does your family cruise stop at the Key West port? Get some quick tips on how to make the most of your day and enjoy this colorful island.

Key West Port | Panoramic photo of downtown streets

We stopped at the Key West port as part of a recent back-to-back Havana cruise on Majesty of the Seas. At the time that we booked our cruise, I had no knowledge about Key West. I knew it was in Florida, That’s it. And, because the Key West port is a Florida port, I assumed that this would be a stop dominated by a beach excursion. But turns out that visiting the beach was not really the top family option!

Key West has many claims to fame. It’s the southernmost point geographically of the United States. And, it’s only 90 miles away from Cuba. Which  is less than the 160+ mile distance between Key West and Miami. And, several famous writers and poets have called Key West home including Ernest Hemingway, Tennessee Williams, Robert Frost, and Shel Silverstein. (If you have kids who are Judy Blume fans, let them know that she lives on the island as well!)

Key West has also served as a vacation destination for several U.S. Presidents: Harry Truman, Dwight Eisenhower and John F. Kennedy. Truman’s Little White House is now a popular museum and tourist attraction.

Finally, the Key West port is also known for its amazing sunsets. Unfortunately, that’s one treat we weren’t able to experience due to our ship’s late afternoon departure.

Key West Beaches

Coastline of Fort Zachary State Park in Key West Port

Based on our pre-trip research, the best beach option appeared to be the beach at Fort Zachary Taylor Historic State Park.  Unlike several of the other beaches in the area, the beach at Fort Zachary remains in its natural state without the benefit of sand shipped in from the Caribbean. It’s a coral beach that’s rocky in texture, so some type of water shoes or flip flops are strongly recommended. The beach snorkeling there receives rave reviews. And, visitors also have the opportunity to tour the historic Civil War fort for which the park is named.

Ultimately, after weighing our options, we decided to explore the island and save our beach adventures for our stop at the Cozumel port.


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Touring The Key West Port

Key West Port | photo of direction signs on Mallory SquareOne of the best ways to enjoy your time in the Key West port is simply walking around. You can have a great time strolling around and popping in and out of shops and cafes. Notwithstanding the absence of a beach focus, the ambiance is very much laid back fun in the sun. The laid back nature of the island permeates the atmosphere like a special kind of humidity. You can almost touch it.

Some of the more popular excursions for the Key West port include two variations of a hop on/hop off bus tour. They were both roughly the same price and kids are free. But, there’s a big distinction between the routes. The Conch Train version stays in the downtown area while the Old Town Trolley version includes ½ dozen or so more stops around the island.

Figuring to get more bang for our buck, we signed up for the longer one as to see more of what there was to see. But, truthfully, much of the extra stops were just hotels or shopping centers.  It was nice to see the overall island, but there wasn’t any real hopping on or off at those extra stops. So, if you have time concerns, you won’t be missing much with the shorter versions. Also, since the Conch Train is an actual train on wheels, your kids may get an extra kick out of that.

Beware Wasting Time Getting Into Town

Our cruise ship docked at the Old Mole Pier, which is owned by the navy. The naval installation has restricted access.  So no pictures were allowed while you are on the pier. And, passengers must pass through a security checkpoint and show photo identification when returning to the pier.

It turned out to be quite the production getting from the ship to our excursion.

For the Key West port call, we decided to book our cruise excursions through the cruise line. The Old Town Trolley excursion included transportation from the ship to town where the hop on/off part started. At first, this sounds like a big benefit. Turns out, not so much. It literally took us two hours from the time we were told to meet in the ship auditorium until we actually started the tour.  Followed by another very long wait standing in the hot sun waiting for the shuttle. (We were never provided an explanation for the extremely long wait times.)

It turns out that a shuttle ride from the Old Mole Pier to town takes about 5 to 10 minutes. And, the shuttle rides into town are free. The Old Town Trolley and Conch Train vehicles are used as part of the shuttle service.

Both the Conch Train tours and the Old Trolley tours can be booked online easily, so we might have been better off doing this particular adventure as an independent excursion. We could have skipped the long wait in the auditorium and hopped on a free shuttle into town.

The Old Town Trolley

Once we got into town, the tour itself was great. The trolley passes by many of the main tourist attractions, so if you plan your time right, you can fit in several activities along with the trolley tour itself. Some of the key highlights:

  • The tour starts and ends in Mallory Square. In that same area you can also visit the Key West Aquarium, Ripley’s Believe it or Not, and Truman’s Little White House.
  • The third stop is near Sloppy Joe’s Bar, a famous Ernest Hemingway watering hole.
  • The next stop (#4) takes you to the popular Duval Street (see below).
  • Stop No. 5 takes you to the Bahama Village where you can stop and visit the Ernest Hemingway House.
  • Stop No. 11 takes you to the Southernmost point.

We had a very low key and relaxing day on the trolley. Everyone could enjoy open air access in the trolley, and the drivers had interesting observations to make along the way. We hopped off for walking around, seeing key sites, lunch and souvenir shopping. 

Roosters in Key West Port

One distinctive feature found in the Key West Port are wild roaming roosters. There are also wild hens with baby chicks, but the colorful roosters are quite striking and hard to miss. Key West locals refer to these proud fowl as gypsy chickens.

Our trolley tour guide provided a brief explanation about the birds. The short version is that settlers brought chickens to raise as sustenance. And, when some folks migrated to the area from Cuba they also brought roosters for cockfighting. At some point, backyard chickens became obsolete, and cockfighting was outlawed. Owners essentially released both sets of birds to fend for themselves, and they have thrived quite well.

Duval Street

The famous Duval Street is essentially the area’s main strip filled with bars, shops, restaurants and many visitors. For those who like to shop, the shoppers in our travel party found some awesome deals at the Coach factory story. It is situated right down town on Duval Street. No need to leave the beaten path to find it. And, there were countless places to pick up traditional souvenirs as well.

Key West has lots of bars. As the tour drivers like to say, it has more bars than beaches. We were there during the middle of the day with kids, so that wasn’t really part of our itinerary. But it is possible to hit some of the more famous spots as part of the bus tour.

The Southernmost Point

The island of Key West is literally the southernmost point of the United States. And, there’s a special marker commemorating it (a very large cement buoy).  This is also one of the places you can hop off the trolley and explore. Lots of people like to stop there and take a picture. There was quite a crowd and a line of people waiting to do so. The wait to take an actual up close and personal picture with the marker is about 1-1 ½ hours. So, if you want to do that, you may want to go there first, and then continue with the rest of your day.

Getting Back To The Ship

Something else to be mindful of is the issue of crowds getting back to the ship. The trolleys used for the Trolley Tour are also used to shuttle people back to the Mole pier.  Late in the day, as more people were trying to head back to ship, there was a very large crowd waiting at the final trolley stop in Mallory Square. Not everyone could fit and most folks had to wait for next buses. By the time our bus pulled up, there were seats for 5 people. But there were about 45-50 people actually waiting.

Popular Activities For Key West Port That We Ended Up Not Doing:

Based on advance research, two kid-friendly attractions stood out: The Key West Aquarium and the Shipwreck Treasure Museum. Because of time constraints and the logistical delays referenced above, we weren’t able to fit either of those in. So we’ll have to save them for a future trip. But here are a couple first hand accounts which show why you should consider including these on your agenda.

Closing Thoughts:

We found the Key West port to be a delightful island to spend a relaxing sun-filled day. Although a handful of beach options exist, you will likely find more engaging entertainment roaming through town.

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