Check out this very thorough walking tour video from Tim Cruise (who also dives into the personality of a similarly named celebrity.)

Tim has great suggestions for a walking tour without a guide. He goes all around Key West and shows easy to follow maps.

You’ll check out restaurants like Sloppy Joe’s (he recommends the sloppy joe) and Bull on the Corner.

Margaritaville and Hard Rock Cafe are close by. I love the Margaritaville restaurants!

The walk through of the Observatory and all its butterflies is pretty incredible.

It wouldn’t be a complete tour without seeing the Southern Most Point in the United States.

He hits up the earnest Hemingway House. It’s $17 and cash only for some reason.

You’re going to get the best view of the island if you walk to the top of the lighthouse stairs.

He touches on Rocky Beach and some beautiful ocean views.

Tim finishes at Mallory Square where you see different street performers including cat & dog performers.

And finally, the sunset is gorgeous.

Key West Walking Tour

Walking tours of Key West are both fun and informative. They often originate around Mallory Square and take 1 – 3 hours. Walking tours send you home knowledgeable about Key West and give you the chance to meet fascinating people. You will remember this tour for a lifetime. Tours focus on history, local homes, haunted activity, food & drink, and many other aspects of Key West.

If you’re looking for a self-guided tour of Key West, check ours out in the “Self Guided Walking Tour of Key West” section below.

There are a few different styles of walking tours:

In-Person, Guided Walking Tours

An in-person walking tour of Key West will provide the most interesting and surprising experiences. A guide with local knowledge should introduce you to the different residents of the area while explaining and answering any questions.

Some of the tours include history, famous past residents, adults-only, and haunted Key West. Expect a lot of talk about Ernest Hemingway and maybe even a little about Jimmy Buffett.

Some that I recommend

Self-Guided Walking Tours

A well-written, self-guided tour will make sure you hit all the important parts of town while allowing you to stroll at your own pace.

For a curated, self-guided tour, see our section below: Self-guided walking tour of Key West.

Self-guided tours are nice because they are often less expensive and possibly free.
As with many things in life, you get what you pay for. If you pay for a self-guided tour, don’t settle for anything that isn’t packed with information and interesting stopping points.

The nice thing about self-guided tours is it’s easier to interact with your group. You’ll be able to interact with friends and family and take turns being the guide.

Depending on how much your kids like to explore, self-guided may be the best option. I encourage my children to learn to their heart’s content.

Self-guided tours of Key West let everyone immerse themselves in Key West’s history and culture.

Also, you can skip any parts that you’re not interested in and get to the highlights.

Selg-guided tours are a great option!

GPS Guided Tours of Key West

If everyone has a phone and can tap into the same lesson, this is a great option!
GPS guided tours may be a little less intimate than self-guided, but they allow everyone to participate in the tour as they prefer.

Make sure to take the headphones off and discuss the interesting points of each stopping point.
What I like about GPS tours is it takes a lot of the work out of it. I get the tour I want and then just follow directions, supplementing the tour by reading displays I’m interested in.

GPS My City’s customizable tour of Key West is a great option.

Digital

Why wait to be in Key West when you could take a digital, video walking tour of Key West right now?

You DO NOT want to skip the real thing, but getting to know Key West before you arrive will help you to know what you want to see and pick the best tour.

And daydreaming about the destination before a vacation is part of the fun!

There are decent walking tours for free already on YouTube. Check out some of these here:

• St. Pete Beach
• Downtown Key West
• The Must See Tour – very thorough walk through.

I recommend watching 1 or 2 videos before a trip and then enjoying an in-person, guided Tour once you arrive.

Careful though, you may know too much about Key West and decide to move here!

Self-Guided Walking Tour of Key West

To give you a little taste of a Self Guided tour, consider the following:

Start at Mallory Square

Mallory Square Site: It’s wonderful to start in the old town, and this is convenient for those arriving on cruise ships.

Continue to

Audubon House & Tropical Gardens

205 Whitehead St, Naval Air Station Key West, FL 33040
After exploring the gardens, take a break at:

Irish Kevin’s

211 Duval St, Key West, FL 33040
This will get you over to Dual Street and is a great little watering hole. Tell them that TravelHabitz sent you!

Now that you’ve rested, start the long yet scenic walk to:

Key West Cemetery

This is going to get you moving a little bit. You may think it’s weird to visit here on vacation, but cemeteries at the ocean level are next-level interesting. They become mausoleums since they have to be above ground.

This is a pretty unique experience and worth exploring a little. There may even be some famous names.

Ernest Hemingway Home

I’m never sure if Key West would be as famous and remarkable a destination if Ernest Hemingway hadn’t lent his personal brand to it.

I guess I’ll let you decide.

Make sure to read all the signage around the home, and maybe pick up a copy of Farewell to Arms before you travel.

Captain Tony’s Saloon

Another great watering hole after you’ve had quite a walk.

Why do a walking tour?

It’s too easy to go somewhere and have the same experience you would have had at home. Traveling hundreds of miles to eat at the same style of restaurants or the same type of food, not learning anything, not experiencing any of the unique experiences Key West has to offer.

Walking tours give force you to intimately experience what is unique about Key West. When you return home, if you can’t describe Key West’s unique drinks, delicious food, and what makes Key West special, then your vacation has failed.

Key West is much more than a relaxing, tropical vacation.

Who doesn’t want to go to Key West? Everyone does it’s gorgeous but there’s so much more that makes Key West unique.

Including a walking tour will create memories and conversations about Key West was an amazing vacation.

Don’t just visit Key West, experience it! Make Key West become a part of you.

FAQ

What is the best walking tour of Key West?

Tough question to answer. Read the reviews to make sure you’re dealing with an honest company and then find a tour that looks the most fun to you.
There are a ton of options. We can’t say which one is the best for you.
Always use the reviews to make sure a company is good. If you feel you can trust a company, give it a try.

Are Self-Guided Walking Tours of Key West safe?

On Key West, yes you can feel confident you’ll be safe. Always pay attention, avoid dark areas, and avoid areas if your gut tells you to.

Self-Guided and GPS Guided tours are more likely to occur in the daytime.

Is a walking tour a good experience for kids?

Walking tours are an amazing experience for kids! They like to be out moving and experiencing. A walking tour is a perfect way for a child to learn the way they naturally do. A walking tour will let them explore, read, and move around, experiencing the actual history.

What’s the least expensive way to do a walking tour?

That’s gonna be a self-guided tour and we’ve got a pretty good one set up for you earlier in the article.

Be ready to call up Wikipedia if you need more info about any destination.

You can set up a fantastic tour that your family will remember if you start with a plan and do a bit of googling along the way.

Cautions

If you don’t have a guide, most of these tours will be during the day.

If you have a guide in Key West, you should be safe. For any other type of tour make sure you pay attention to your surroundings and what is going on.

In Key West mostly you’re safe but just be aware of your environment. If anything makes you nervous, trust your gut.

Summary & other places of interest

I hope Key West gives you incredible sunsets and sunrises, some nice cocktails, and memorable stories that your friends will enjoy. I hope you find a lot of satisfaction in your Key West and Florida Keys vacation.

This is such a fun destination and I wish everyone could visit at least once.

Enjoy the different bars and restaurants and make sure to stay safe.

Key West is probably the most practical place on the planet to have a walking tour.

Other places to check out while you’re in the area are Smather’s Beach and the Key West Nature Preserve.

If your vacation includes mainland Florida in the Miami or Fort Lauderdale areas, I recommend checking other attractions like Everglades National Park, and the Homestead Bayfront Park.

Even taking this little drive from Miami to Fort Lauderdale gives some incredible views.

Walking tours are nothing new for travelers — I hope Key West is the first of many experiences where you immerse yourself in the destination.

Miami to Fort Lauderdale

A basic driving trip from Miami to Fort Lauderdale takes about 40 minutes to an hour. Rush hour usually isn’t too bad- a little more than an hour at most. The scenic way to get there is taking the A1A to Dania Beach, but there are times this can be a frustrating route.

Exploring these to gem cities of Florida is high on the bucket-list of many people.

There isn’t what I’d consider a good bus option.

• Driving: 40 minutes to an Hour
• Rush Hour: 1 to 1.5 hours
• No Tolls: 40 minutes to an hour
• Train: 30 to 90 minutes depending on point of origination
• Other Public Transportation: no legitimate options – Grey Hound does have a route, but requires transportation to the bus station.
• Biking: 3.5 to 4 hours. Recommend biking on the A1A
• Walking: 12+ hours. This is going to be 30+ miles and longer than a marathon. Would be interested to hear from anyone who has actually walked this.

Getting to Fort Lauderdale by Car

Miami to Fort Lauderdale: Driving the fastest route

The direct route to Fort Lauderdale is pretty easy: take Interstate 95. If it is currently rush hour, you’re going to want to take the express tollway. But if you’re traveling during less busy times you should be fine and get there just as fast.

The Scenic Drive to Fort Lauderdale

There are a lot of cars but a couple of routes worth seeing.

Recommend Alton Road or A1A but aggressive drivers can get frustrating.

It’s great at the beginning to see Big Pink to your right. The entire drive is peppered with residential units & hotels.

I love seeing the Fontainebleau. I think of the iconic card game between James Bond and Goldfinger every time.

You may want to avoid this drive during certain times of the year (cough… spring break).

No Tolls: Miami to Fort Lauderdale

This is not much different than the fastest direct route above. Just make sure you don’t get on the express lanes. If it makes it easier, select the no tolls feature on your GPS. However, keeping an eye out for the signs is simple.

Train from Miami to Fort Lauderdale

It’s possible to take a combination of Miami Metrorail and the Brightline Express Train to make this trip. It would cost from about $23 to $45 each way — possibly higher depending on where you start and end in each city.

The Brightline train will eventually connect Miami to Orlando.

Biking to Fort Lauderdale

This route is similar to the scenic driving route. Take the options that keep you closest to the ocean.

Walking to Fort Lauderdale

I’m not sure this is even advisable. If this is something you want to do because you enjoy the scenery and distance, you would be better off signing up for the Miami Marathon. It has similar access to Biscayne Bay and the Atlantic Ocean and would be a gorgeous run.

If this is something that you have done, we would love to hear about it please reach out on Twitter or Facebook and let us know how it was.

FAQ

What is the BEST Travel Option from Miami to Fort Lauderdale?

I recommend driving.

Miami is big. Fort Lauderdale is big. Florida is big! Take a car.

The train may work if you’re just going to visit one area and it will be easy to get around after you arrive.

If you’re looking for beautiful scenery or a drive in nature, you would be better off getting out of these areas anyway. The car will be more practical.

Is there good public transportation?

Brightline is decent, but still not convenient compared to public transportation in other parts of the country. That is not unique to this part of the world.

Travel in this area largely occurs by car.

Cautions

No cautions unique to this article. As in any major metropolitan area, be safe. Lock your car doors, hide your valuables, and stay in well-lit areas.

Much of the driving will be congested. There is some gorgeous scenery and beautiful architecture, but keep your eyes on the road.

Summary

There are many more destinations in this part of Florida to explore. Miami & Fort Lauderdale are hot destinations and both offer amazing experiences.

If you’re in Miami, for art check out the Pérez Art Museum or the Wynwood Walls. You’ve also got HistoryMiami Museum and Little Havana.

On the Fort Lauderdale side of this trip, check out the Museum of Discovery and Science, or the Bonnet House Museum and Gardens.

And of course, both places are covered in beaches and ocean parks!