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Here Are The Best Family Things To Do In Key West Port In A Day

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

In many ways, Key West is a hidden gem when it comes to cruise ports. We had sailed more than 15 different Caribbean cruises before sailing one that included a stop at the Key West Port as part of a Havana cruise itinerary. Perhaps it doesn’t appear on the more frequent list of Caribbean cruise port stops because of its small geographic footprint, or because it’s not really a traditional beach destination. But regardless, there’s plenty of things to do in Key West that don’t involve the beach or water sports, yet still involve lots of vacation fun.

What Is Key West Famous For?

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. You can purchase Little White House tickets online.

Finally, the Key West port is also known for its amazing sunsets. Unfortunately, that’s one treat you won’t be able to experience if your ship has a late afternoon departure.

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What Is There To Do In Key West For Families?

Walk Around 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.

Ride The Trolley or Train

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 to see more of what there was to see. But, truthfully, many 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.

A Tip For Saving Time & Money

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 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 you might be better off doing this particular adventure as an independent excursion.

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 is the 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 downtown 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.

Alternatively, you can check out this site on the live webcam. There’s a live webcam of the Southernmost Point. It pretty much shows you what you will see if you go, except for the long lines which are just outside the frame.

Shipwrecks & Treasure

It’s believed that more than 1,000 ships have wrecked in or near the Florida Keys over the past few hundred years. The abundance of coral reefs, unexpected shifting sands and water depth and hurricanes, and other poor weather conditions have all played a role.

The Shipwreck & Treasure Museum

If you’re interested in learning more about the shipwrecks around Key West and the treasures they may contain, you have two main options: The Mel Fisher Museum and the Shipwreck Treasure Museum.

The Mel Fisher Museum

The Mel Fisher Museum contains an extensive collection of artifacts from 17th-century shipwrecks, including treasures from Spanish Galleons and historical artifacts from a wrecked slave ship. This museum also offers a lab tour where visitors can see how history is revealed through excavation and conservation of shipwrecks. 

The Shipwreck Treasure Museum

The Shipwreck Treasure Museum also provides insights and information into the shipwreck history of Key West, but it’s more from an entertainment perspective. It combines actors, films and actual artifacts to tell the story of 400 years of shipwreck salvage in the Florida Keys.


Other Child-Friendly Attractions in Key West Port

Key West Lighthouse & Keeper’s Quarters Museum

The highlight of this is experience is climbing 88 steps to the top of the lighthouse to take in the panoramic 360-degree views.

Key West Aquarium

A small, historical Key West Aquarium first opened in 1935. You will find fun things to do, but you should manage your expectations. This is not Sea World.

The key is to go when there are scheduled activities and tours you can participate. There’s not so much to be had if you’re just walking around on your own. Educational talks and feedings occur about every 30 minutes. Most noteworthy are the touch tanks and the shark tank.

At the touch tanks, visitors can get up close and personal with stingrays, conch, sea cucumbers, moray eels, barracuda, and more.

As for the shark tanks, there’s a smaller open-air indoor tank where guests can feed the sharks. And also a larger outdoor tank where you can watch employees feed the sharks. 

Best Key West Beach Option

Coastline of Fort Zachary State Park in Key West Port

You will find the overall best beach option 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.

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 the next buses. By the time our bus pulled up, there were seats for 5 people. But there were about 45-50 people actually waiting.

Closing Thoughts:

If your itinerary includes a stop at the Key West Port, you’re in for a special treat. Key West port to be a delightful island to spend a relaxing sun-filled day with plenty of family-friendly options that appeal to a range of age groups.

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