Key West Family Travel Guide

I’ve dreamed of visiting the Florida Keys ever since our family moved to Florida. I’m not sure if it was the island culture that drew me in, or just a desire to visit the most remote part of our state, but either way I knew I had to go.

Visions of flip flops and cut-off shorts danced in my head as I planned our vacation. There would be slow mornings sipping Cuban coffee, long days roaming the streets of Key West, and strong tropical drinks in the evening. It was bound to be the most relaxing time in our family’s life.

Then I snapped back to reality and remembered that I had 3 little kids. Nothing is relaxing.

But I will say this about Key West: living on island time kind of seeps into your bones and you really do start to let go of the feelings of stress that regular everyday life brings. Unfortunately, my one-year-old didn’t get the island vibes memo, but we had an incredible time in the Keys nonetheless.

Related: 13 Mistakes You’re Making When Traveling with Toddlers

I know Key West isn’t traditionally thought of as the most family-friendly place, and it’s true that there’s definitely a party culture there, but in my experience it was easy to avoid that and find plenty to do with little kids. You just have to know where to look!

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WHAT TO DO IN KEY WEST WITH KIDS

Old Town Trolley Tour

 Old Town Trolley Tour in Key West, Florida

My kids love a trolley tour, what can I say? I’m also a fan, because it means my kids are sitting still, mesmerized by the views so I actually get to listen to the driver and tour guide. Usually they’re pretty funny and always very accommodating to strollers and little kids. It’s a great way to get a feel for the city before you start exploring, and if you find a good parking spot you can just use the trolley as transportation since it’s hop-on-hop-off.

We found free street parking a few blocks away from the Southernmost Point one morning, then were able to buy our tickets at Stop 11 - Southernmost Point Trolley Stop. There was a little shop where you could buy the tickets, and we also picked up our post cards (the only souvenirs the kids usually get), a knick knack for my husband’s desk for much cheaper than we saw anywhere else, and cheap sunglasses for me since I forgot mine.

Buy tickets for your trolley tour here.

Mallory Square

 Mallory Square in Key West with Kids

During the day, Mallory Square just looks like a big plaza near the harbor with great views and lots of space for the kids to run around. In the evening it turns into a giant festival for the Sunset Celebration which takes place every night (more on that later).

We found some great little shops for souvenirs around Mallory Square, and an excellent slice of Key Lime Pie.

Duval Street

Duval Street is the main thoroughfare running from one end of Key West to the other, and there is not shortage of bars, restaurants, or souvenir shops and boutiques. Sometimes it’s nice to just stroll along and duck into whatever eatery or shop catches your interest. Just beware if you have kids that can read: some of the t-shirts in the windows of these souvenir shops are less than polite.

Ernest Hemingway Home and Museum

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One block off of Duval Street you’ll find the home of famous author Ernest Hemingway. He was one of my favorite authors in high school after reading The Sun Also Rises and The Old Man and the Sea, then The Paris Wife (not authored by Hemingway, but about his early adulthood), so I knew I had to make a stop here.

Since my husband had no interest in this museum, and we knew our one-year-old would destroy important and very old things if we let him walk around a museum, we decided to split up. I took our 5-year-old daughter with me, and my husband strolled Duval Street with the 1- and 3-year-old.

I’m glad we made that decision. My daughter kept very busy finding all the cats roaming the property. They are all descendants of Hemingway’s cats, and there’s even a cat burial site somewhere on the grounds where they all have their own gravestone (and really fun names!). See if you can find the 6-toed cat!

 Hemingway’s Office

Hemingway’s Office

While my daughter was finding and counting the cats, I was fascinated to soak up everything I could about Hemingway’s life in Key West. I was blown away by his office, and can only hope that someday I’ll be a successful enough writer to have an entire separate room, nay, building where I can escape to write in peace.

Anyway, you certainly can bring toddlers here, but unless yours is quite well-behaved and doesn’t destroy everything in site, I might consider waiting until they’re a bit older. There’s not really much space for strollers and there are a few staircases, so you’ll have to carry them. 2 and up will probably be distracted enough by the cats that you can actually listen to the guided tour or read the signs!

Buy your tickets on site, but be aware that it’s CASH ONLY.
Hemingway Home and Museum Website

Key West Aquarium

Not the world’s biggest or flashiest aquarium, but you will find a shark feedings, a touch tank, tropical fish, and more! It’s located near Mallory Square right next to the Sponge Market and Trolley Stop.

Read more and buy tickets here.

Air Adventures Helicopter Tour

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Kids are more than welcome on a helicopter tour of the island! The pilot told me that kids under 2 can sit on your lap, while kids 2 and older will need their own seat. He said around 5-8 are the most magical ages to bring little kids, but any age is welcome!

My husband and I just took tours while our friends stayed back at the hotel with the kids while they napped. We did the the Key West Eco Tour which lasts about 20 minutes and covers all of Key West and includes the backcountry shipwrecks, reefs, and wildlife (think sharks and stingrays you can see from the helicopter).

The views were spectacular and the water was stunningly blue and clear. Our pilot was so knowledgeable and we could hear her narrating the tour through the headphones we put on at the beginning of the ride. You also get a microphone you can turn on if you have questions.

I would highly recommend this tour for adventurous families, especially if you like to have more unique experiences! You’ll definitely make some once-in-a-lifetime memories on the helicopter tour.

Book your tour here.

Sunset Celebration

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 Mallory Square at Sunset

Mallory Square at Sunset

Sunset Celebration takes place every evening in Mallory Square, so make sure you make it down to that area one of the nights you’re there. You’ll see performers and singers around the plaza entertaining the crowds, so feel free to stroll around and take in the sights.

Find the stand that’s selling juice out of pineapples and coconuts and BUY ONE. The lady selling them is super nice, and she will offer you a free refill of juice. Also, it’s just a great photo opportunity, and so worth the $8 in my opinion. They are non-alcoholic so your whole family can enjoy it together!

Find a spot somewhere along the waterfront to watch the sunset and just sit, relax, and enjoy!

Southernmost Point

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Ok, this is a very touristy thing to do, but that’s half the fun! There’s a giant buoy stationed at the Southernmost Point of the Continental USA, so tourists line up to take pictures next to it. It’s very unassuming, just sitting at the end of a sidewalk right in front of the ocean. No signs, no office, nothing official like that. It’s free to do, but there might be a line. Get there early and you should e fine! We got there sometime between 8:30 and 9 and only had to wait for 2 families.

Fort Zachary Taylor

We actually did not make it to Fort Zachary Taylor Park, but I’ve heard it’s the best beach on the island. Since we spent an entire day of our trip in Dry Tortugas National Park where we got plenty of beach time and snorkeling, we decided to use what little time we had left in Key West sightseeing.

Anyway, this is a state park, so you’ll have to pay about $6 to get in, but once you’re in it’s a great beach with excellent snorkeling and diving. You can explore the fort, go hiking, have a picnic in the shade, or just sit and enjoy the view.

Find out more here.

Dry Tortugas National Park

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You can only reach Dry Tortugas National Park by taking a 2.5 hour ferry boat ride out to the remote island, or by chartering a sea plane. If you’re working on checking off as many national parks as you can with your kids, I would highly recommend doing this one while you’re in Key West. It was stunning, and when we stepped off the boat we felt like we were in a screensaver picture. The water seemed too blue for real life.

You can explore Fort Jefferson, either taking the tour or doing a self-guided tour. You can even climb up to the top of the Fort and get an incredible view of the ocean. In addition to the Fort, you can snorkel, relax on the beach or swim, bird watch, walk on the Moat Wall, and even set up camp there if you’ve planned to camp overnight.

To me the only downside of taking a day in the Dry Tortugas is that if you have young kids like me, it will be time to feed them dinner and put them to bed by the time you get back to Key West, and since you have to check in at 7 a.m., you essentially take an entire day of your trip to do this National Park. If your kids are older, you can easily spend time exploring the Historic Seaport after you return, or head to Mallory Square.

Dry Tortugas National Park Website

GETTING TO KEY WEST

Half the fun of visiting Key West is road tripping through the Florida Keys first and stopping at many of the quirky attractions along the way!

Related: 50 Road Trip Activities for Toddlers and Preschoolers

Miami

If you’re starting your drive from Miami, you’ll find plenty to do in that area. My personal favorites are Little Havana and Coconut Grove, so definitely make sure to explore those neighborhoods if you’ve got some extra time in the city.

Related: Miami Family Travel Guide

On the drive down to the Florida Keys you’ll pass through Homestead where you’ll find Coral Castle, a limestone structure and series of sculptures built by one man without any help from machines (it’s fascinating), and the Robert Is Here Fruit Stand where you can stop for fresh produce and smoothies.

Key Largo

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Conch Fritters Key Largo
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Key Largo will be the first of the Florida Keys to drive through, and yes, you will have that Beach Boys song “Kokomo” stuck in your head the entire drive. “Key Largo, Montego, baby why don’t we go, Jamaica…off the Florida Keys, there’s a place called Kokomo…”

We stopped at Alabama Jacks for conch fritters, and we loved the atmosphere. It’s an open air dive bar/restaurant with paper plates, a roll of paper towel on the table, and license plates hanging on the walls. We found it to be perfectly kid friendly with a kid’s menu and high chairs. It’s also right on the water so you can walk around and look at the fish with the kids while you’re waiting for your food.

If you have plenty of time to stretch out your road trip and your kids are a little older, you might want to stop and snorkel or dive in Key Largo at John Pennekamp Coral Reef State Park. It’s an underwater park with coral reef, tropical fish, and the Christ of the Abyss Statue. There are also boat tours, kayaking, and canoeing.

Islamorada

 Robbie’s Marina of Islamorada

Robbie’s Marina of Islamorada

Once you get to Islamorada, you’ll start to feel more like you’re in a tropical destination. Be sure to pull over at Robbie’s Marina where you can feed buckets of bait to the hungry tarpon below. Yes, all 4 adults in our group were terrified to do it and we were all giggling like school girls as we hung our arms over the side of the dock waiting for one of the fish to take our bait and jump out of the water.

We got some great pictures and videos here out on the docks, and all the kids came with us. Just be aware that the pelicans can get a little aggressive, especially if you leave your bucket of dead fish unattended. They even snatched a fish out of my husband’s hand while he was about to feed the tarpon. It was hilarious, but might freak your kids out a little bit. (I still think it’s worth it to do!)

After the obligatory tarpon-feeding, there’s plenty of shopping to do at the stalls around the marina. There are the standard souvenirs and gifts, wooden signs and decor, and beachwear. It was really fun for the kids to walk around, and we let my daughter pick out a bracelet from the tables upon tables of handmade jewelry.

WHERE TO EAT IN KEY WEST WITH KIDS

For the most part we chose to prepare our meals in our rental place since we had access to a full kitchen and were with another family. It’s so much easier to not eat out when you have toddlers, and cheaper, too! There were a few places that caught our attention, though.

Related: Healthy Road Trips Snacks for Adults, Kids, and Toddlers

Cuban Coffee Queen

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I liked this place so much we went there twice. It was worth it because I had the best iced coffee of my whole life. It was iced Cuban coffee with coffee ice cubes and a vanilla flavor shot. I was living my best life sipping that sweet nectar of the gods, strolling past a crowing rooster, and soaking in the sunshine.

Anyway, the shop is super cute. It’s open-air, and tucked into a little plaza away from the bustle of Duval Street. The food there is reasonably priced and delicious, too. A great place to stop and eat especially if you have a busy toddler or energetic kids who want to burn of some energy, since there’s all kinds of space to move, walk, and run in the courtyard area.

Sunset Pier

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You know when you look up Key West on Instagram and you find all of these pictures of brightly colored tables and chairs on the waterfront? Yeah, this is that place. It’s located right off of Mallory Square, and has rows and rows of colorful outdoor seating. Only downside? They only have high boy tables with tall stools. Not exactly the most toddler-friendly. Prices are a bit on the higher side, too.

However, if you’re looking for a place to park yourselves for the sunset while enjoying some tropical beverages and snacks, this is it. Plus it makes for a great photo opp.

WHERE TO STAY IN KEY WEST WITH KIDS

We booked only a few weeks before our trip, and we were traveling on the days right before Thanksgiving. There wasn’t a lot available, and prices were quickly rising. I guess that’s what we get for waiting to book last minute for a holiday week!

Anyway, we ended up finding a few great options that I want to share with you.

Related: Tips for Getting Your Kids to Sleep in a Hotel Room

Ocean’s Edge

This was the place I had originally booked with one bedroom, but we ended up finding a place a few days later with two bedrooms. Anyway, the price was great and the resort looked absolutely beautiful. I would definitely consider booking this place if we ever came back to Key West.

Vacasa

We ended up booking a 2-bedroom condo through Vacasa for our stay in Key West. Like I mentioned, we were traveling with another family who also had a toddler, so it was really nice to have the kitchen and plenty of space for our kids to run around and be kids.

I truly think at this stage in our lives, renting a home or condo is just so much more relaxing than trying to keep the kids quiet in a hotel room. Hotel rooms can totally be done, and we’ve stayed in some amazing ones, but the extra space is always appreciated.

Anyway, we stayed at the Sunrise Suites Resort which was away from all the action of Duval Street and Mallory Square, but it was nice and quiet and felt like a respite at the end of the day. We really loved it! They have lots of rentals closer to the action, too, if that’s what you’re looking for.

Airbnb

I recommend looking for an Airbnb for the same reason we used Vacasa. A vacation rental will get you more space and a full kitchen for prices similar to hotels and resorts. You’ll feel like you have your own private space to retreat to, and you can really make yourself at home. Use my link to get $40 off your first booking with Airbnb.

…or search now for other properties!

Booking.com

We had such a blast in Key West with the kids, and I could definitely see returning when they are a little older to do some more exploring, hiking, and biking around the city. I hope this gave you some ideas for what to do while you’re in Key West with your own little ones!

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