Key West with Kids and a 4-day Key West Itinerary

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This summer I had to renew my passport, so I knew our end of summer adventure would be a stateside one. Since I’ve planned many Florida Keys trips for lucky clients, I knew I wanted to get down there and explore. This August, we did a split stay between Key West and Hawks Cay on Duck Key, and as always it was an epic adventure. We had the best time and I’m so excited to share my Key West with kids itinerary with you!

Key West with Kids

Key West with Kids and a 4-day Key West Itinerary


Every August, we do our big end of summer trip. This year, with camp ending so late, school starting before Labor Day, and my previous passport out for renewal, it was the perfect year for a Florida Keys family trip.

Last summer we did the Grand Canyon and a southwest road trip, and I knew that would be a hard one to top!

I’ve planned a few Florida Keys trips for clients, and I knew I wanted to do a split stay and check out as much as possible in seven nights.

When I booked this trip, Delta was offering a daily direct flight from LaGuardia to Key West. Yes, Key West has a small airport making it much more convenient than flying into Miami and driving.

Key West with Kids

But in early summer we got that dreaded schedule change notification that they stopped that direct route and we would have to connect in Atlanta to fly to Key West.

After weighing all the options (and having already booked all the hotels and tours in the lower keys), flying in and out of Key West still seemed to be the best option.

Over three nights we got to see and do so much in Key West with kids. Here is our 4-day itinerary and trip report.


Key West with Kids Day 1- Flying to Key West and relaxing at our hotel

Our flight out of JFK was at 6am, so we had an early wake up, and arrived in Key West before noon. We did have a short layover in Atlanta but the trip was easy and painless.

Once we got our luggage in Key West, we hopped an Uber to our hotel, the Key West Marriott Beachside Hotel.

This hotel is located closer to the airport than the downtown, which was perfect for visiting Key West with kids.

Key West Beachside Marriott

The hotel offers an hourly bus shuttle to downtown, along with 3x a day a water taxi as well.

There is a nice pool area and a beach you can sit at, not swim at. Although they do offer all the water sports (kayaks, jet skis, etc.) you might need.

When we arrived our room was not quite ready, so we spent the day at the pool swimming, relaxing and napping!

Key West Beachside Marriott

Around 4pm it was finally time to check in and get settled.

I also had set up an Instacart delivery – which is a great way to stock up on food and drinks when you don’t have a rental car. I like to order breakfast food, snacks, water, and wine.

The first night we were totally wiped, so we opted to try the on-site restaurant for dinner. It was fine and by 9pm everyone was ready for bed!

Dinner at Key West Beachside Marriott

PS If you are heading to Key West with kids, or no kids I HIGHLY RECOMMEND picking up this novel, The Last Train to Key West, before you go! This historical fiction book gives a great insight into what the island was like back in the 1930s and I so enjoyed this book!

Key West with Kids Day 2- Exploring Key West with Kids


This was our main day for exploring the city of Key West. I started the day with a two mile walk and we had breakfast in the room at our hotel.

The Key West Beachside a Marriott offers a thrice daily water ferry to downtown, so we took the first boat of the day, at 11am.

Key West Beachside Marriott Water Taxi

Key West Pro-tip: there are also hourly bus shuttles from the hotel.

The ferry dropped us off at A&B Lobster House on the north end of the downtown.

From there we walked over to our first site of the day, the Truman Little White House. This is the house president Harry Truman spent much time in during his presidency.

Truman Little White House Key West Florida

We arrived around 11:35 and waited for the noon guided tour. You can self-tour the grounds but to get in the house, you need to wait for the tour.

The tour was excellent (top of the entire trip for me) And lasted less than 45 minutes.

After the Little White House, we continued to make our way south and stopped for lunch at Blue Haven.

Where to eat in Key West with Kids: Blue Heaven

This is a must do in Key West, but note they only serve pancakes until noon. I wish they had that info on their site, because that’s what my kids were planning to eat! But we all found something yummy and we loved checking out all the random decor around the outdoor restaurant.

After lunch, we finally made it to Duval Street and walked to the south end.

We visited Key West the last week of August, and let me tell you, it was hotter than hades! I believe the temperature that day was close to 100 degrees, with 100% humidity. It was like touring around in a sauna!

So along the way, we had to stop in multiple shops just to get some relief. We didn’t buy much but we looked at every souvenir in search of that much needed air conditioning.

Just before the end of Duval Street we ducked into the The Key West Butterfly and Nature Conservatory, as this was a highly recommended activity, and it was indoors.


Key West with Kids Butterfly Museum

We spent about a half hour with the butterflies, then we were pretty spent. Since we were at the end of Duval street (about 2 blocks over) is the southernmost point buoy, so we had to brave the heat to get a picture!

The line to get a picture was only about 15 minutes and I’m such a geography nerd I loved this! I mean,  we were closer to Cuba then to the nearest Wal-Mart!

Key West with Kids - Southernmost Point Buoy

After that, we were all hot and tired, but it was too late to head back to our hotel, because we had to be downtown at 6pm for the sunset cruise I had booked.

So for about two hours, we wondered around, in and out of shops (aka air conditioning), had ice cream, got a picture of Mile Marker 0, and ran into my friend Amanda who was visiting from central Florida!

Finally it was time to check into our 6:30pm, two hour, sunset cruise.

Key West with Kids Sunset Cruise Commotion on the Ocean

We booked the Fury, Commotion on the Ocean. The cruise left back from the north side of the island where we started our day so we truly had walked all over the island!

The sunset cruise was so great! They had live music, snacks and drinks. Plus sailing along to see a beautiful Key West sunset. We all enjoyed this, even the kids!

Key West With Kids Sunset Cruise Commotion on the Ocean

Lastly, when we disembarked, we ducked into Kermit’s for a slice of delicious Key Lime pie! What a great way to end an amazing day in Key West with kids.

Kermit's Key Lime Pie in Key West Florida

Key West with Kids Day 3 – A day trip to the Dry Tortugas

Yes, this part of the trip was completely action packed! We were up early and out the door by 7am to catch the Yankee Freedom boat to the Dry Tortugas.

Yankee Freedom III Ferry to Dry Tortugas National Park

The Dry Tortugas are a chain of islands 70 miles northwest of Key West. There is a historic fort and national park there as well. These islands are only accessible by ferry, private boat or seaplane.

If you are interested in this day trip – definitely book in advance because there is only one ferry a day and it does sell out.

Some of my blogging friends have full reviews of the Dry Tortuga’s day trip so I won’t go into too much detail,  but this was a full day with two, 2.5 hour boat rides and about four hours on the island to explore.

Yankee Freedom Ferry to Dry Tortugas National Park

I love being on a boat! SWIMSUIT | SUNGLASSES

One the way out, breakfast was provided and, on the island,  you could come back to the boat for lunch (Jersey Mikes subs + there were alternative options for special diets and PB&J for kids).

Once on the island you could do a 20 minute, or 60 minute fort tour (or self-tour the fort which is what we did). Snorkel gear is included with your ferry ride and there are two beaches for snorkeling.

For Jefferson National Park in the Dry Tortugas

Our favorite part of the day (and maybe the whole Florida keys trip) was swimming in the crystal blue water of the north beach. This was really an amazing day and I highly recommend this excursion if you are visiting Key West with kids.

Snorkeling in the Dry Tortugas

We returned to Key West around 5:30 and took an Uber (our preferred way of getting around Key West with Kids) back to our hotel. We ended up walking over to Hurricane Hole for a late dinner before heading to bed.

Swimming at Dry Tortugas National Park
YES! That water was amazing!

Key West With Kids Day 4 – Leaving Key West and Heading to Duck Key

On Saturday morning, we had another half day to spend in Key West before going back to the airport to pick up our rental car and drive to the middle keys. Before check out, we decided to spend some more time at the Key West Marriott pool.

The Key West Marriott offers an airport shuttle, which was a nice, comfortable, cheap way to get back to the airport to pick up a rental car.

We were sad to be leaving Key West, but left excited to explore more of the Florida Keys!


Things I had Wish I Had done in Key West with Kids

As much as we did do in Key West with kids, there were a few things we didn’t have time for, and I’ll have to try on our next trip.


Truman Little White House Key West, Florida
Hanging with Harry Truman (Its a wax statue) at the Truman Little White House

Where to Stay in Key West with Kids

I really liked where we decided to stay on this trip – the Key West Beachside Marriott. I liked that this hotel had more of a resort feel (for Key West at least), and was close enough to the action, but a little removed from the craziness.

This hotel is also an all-suites hotel, so we had a ton of space – a true one-bedroom, a full kitchen and a living room/dining room as well. With an hourly shuttle to downtown and a thrice daily water taxi, getting to Duval Street was quick and easy.


Other Key West hotel options for families include:

The Gates – near the Marriott as well.

24 North – also near the Marriott so removed from the heart of downtown

The Laureate – close to the Marriott, an all-suites hotel recommended by 2Travel Dads.

Southernmost Beach Resort – if you want to stay downtown, this is a great location at the end of Duval Street.

The Reach, Key West – a Hilton property that has a small beach

Key West With Kids

How to get Around Key West with Kids

You can drive around Key West, but I wouldn’t recommend it. Mainly because the parking is tight. We did a lot of walking, which was exhausting in the heat. Instead, the best ways to get around Key West with Kids:

  • Uber/taxi – that’s what we did. Ubers were reasonable and came super quick
  • Rent a golf cart – this seems to be the best way to get around if you want your own vehicle.
  • Conch Train or Old Town Trolley – this is a hop on/off ticket that takes you all around downtown. I initially thought the tickets were expensive, but to be honest, walking around Key West in the heat, I had wished we had bought tickets for this!

Key West Golf Cart Rentals

I loved our trip to Key West with kids. It was super fun with so much to do and see. I had never been, and I can’t wait to go back (with kids or not). Have you been to Key West with Kids? Without kids? Did you love it?

Key West with Kids

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