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Family-Friendly Activities in the Florida Keys

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Thinking of visiting the Florida Keys? Contributing writer Margot Black planned a road trip with her family, and discovered some family-friendly activities and hotels along the way. 

I had not traveled to the Florida Keys since I was a little girl and was excited to plan a trip there with my own family in tow. The Florida Keys are a rare part of the United States where its reputation undeniably precedes it. Whether you know it from movies such as Key Largo or Miami Vice or the books of Ernest Hemingway, there’s something exhilarating about driving along a single road knowing that magic, history, and nature await.

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I wanted my son to be able to enjoy its natural beauty, and so my aim was to allow him to meet as many animals as possible, and also enjoy the ocean and coral reef. We ticked all the boxes and had an extraordinary time. There are around 1,700 keys in the Florida Keys and the biggest, Key West, can be found 129 miles south of Miami. At this point, you are nearer to Cuba, which is 94 miles away across the water.

In its early days it was a Spanish colony, but on March 25, 1822, Lt. Commander Matthew C. Perry sailed his schooner to Key West and planted the U.S. flag, claiming the Keys as US property. Bizarrely, no protests were made over his claim, so from that moment on the Florida Keys became the property of the United States.

Key West is a balmy, tropical location, and up to now, the only part of the U.S. that has never experienced a frost or a freeze (only the shaved ice you eat to cool down). It has a large port, which hosts many packed cruise ships on a daily basis and an even larger naval base. For a little piece of land that measures just two miles wide and four miles long, it packs a punch.

We also stayed for one night in Islamorada, which is just south of Key Largo and about 80 miles north of Key West. Our pit stop here on our drive back to Miami airport split up our travel time, which we all appreciated.

Islamorada means “purple isles” and is known as the Sport Fishing Capital of the World. As well as all the fishing – and excellent sea food – people come here to enjoy all kinds of watersports, kayaking, jet skis, parasailing, boating and sunset cruises. I loved this little Key and we will definitely return one day.

Key West

Where We Stayed: The Chelsea House Hotel

We were lucky enough to stay in two hotels during our four night stay; the Chelsea House Hotel, which is a Historic Key West Inn, and later at La Siesta hotel on Islamorada.

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While the charming and friendly whitewashed Chelsea House Hotel in Key West isn’t specifically billed as family friendly, it suited our needs; there was a family in the room next door with a baby, so we felt very much at home. This boutique accommodation is located in the Old Town part of the island, which meant that we could walk to Duval Street for some crawfish and key lime pie – but nowhere on Key West is too far from anything.

Our suite was adorable and perfect for our two night stay. Happily for me, it was just a few paces from their poolside breakfast buffet and coffee pot. I don’t think I’ve ever slept closer to poolside coffee. We made the most of our breakfasts, which were included in the price (a family travel must), and enjoyed waking up feeling surrounded by historic charm. We were close enough to the water to dash to the sea daily. The ocean is so vividly blue that when my son first saw the ocean, he asked: “Did they color the water?”

Activities in Key West

Key West Butterfly and Nature Conservancy

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I’ve never seen as many butterflies in one place at one time, and my son got a little wigged out, but I loved it. I could have lingered all day. You can stroll through their bright conservatory, which houses 50 to 60 butterfly species, or “flowers in the sky” as they call them here. They will land on you, which is rather fun and magical—and surprising at first. All this is set against a tropical backdrop, with cascading waterfalls and trees—it really is very special.

There’s a lovely gift shop and also an art gallery where you can buy some unique butterfly-themed art pieces. We were educated in their Learning Center about the life cycle, feeding, and migratory world of the Monarch. It was a perfect nature zen garden.

Hemingway’s Home

Ernest Hemingway’s House is a true Key West landmark, and while there’s no need to reserve tickets in high season, it’s wise to get there early. We toured the house, which was built in 1851 and set in beautiful grounds.

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Hemingway lived there from 1931 to 1939 with his wife Pauline and their two sons Patrick and Gregory. He famously kept six-toed cats, and there are currently around 40 to 50 roaming the grounds. I thought the house might be tacky, but you can sense the history. He wrote A Farewell to Arms, Death In The Afternoon and To Have and Have Not while living here. I also loved their book store and wanted to buy everything in it.

My top tip would be to get here early. We were there when the doors opened and had it to ourselves for an hour before a large party of cruise ship tourists arrived. My son Jett was enchanted and said upon leaving, “I want to come back here.” I couldn’t agree more. I don’t know anything better than a cat and a typewriter.

After we left, we wandered along Duval Street, the main street in Key West. We paid a guy $20 to ride us up and down on his trike cab, which was hilarious – and a lot easier than walking (especially with a tired kid) and there was enough room for the three of us.

Fury Dolphin Watch

This is one of Key West’s most popular attractions and has been adding joy to people’s vacation time for almost three decades. Fury boast an expertly maintained state-of-the-art fleet of boats, and you can choose from one of their three catamaran Reef Snorkeling boats, a Parasailing boat, and a chance to see marine life without getting wet on their Glass Bottom Boat. They also do sunset cruises.

It was beautiful but, my tip is to only bring what you need because everything will get wet. The dolphins are really fun and friendly around there and we had two female captains, which I appreciated. It’s a glorious way to get out onto the water.

Also, as a little bonus, while we were hanging out on the dock we saw a manatee go by. Our kid loved it and put his hand in the water to wave to it as it slowly slid under the dock. It was such a treat.

Islamorada

Where We Stayed: La Siesta Resort

We only stayed at La Siesta on Islamorada for one night, but it’s everything I dreamed a hotel in the Florida Keys would be. Lazy, beautiful, intimate, family-friendly – I wish we could have stayed a week here. We wanted to move in and never leave.

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It sits on six acres of oceanfront and miles of white sand, so right there you have perfection, especially with a child to entertain. They have a big swimming pool, a fresh water pool and a hot tub. Their $25 resort fee includes continental pool side breakfast, parking, wi-fi, bikes, fishing poles, kayaks, paddleboards, peddle boats, coffee, towels and local calls. Again, very handy with a kid. We will never not stay in a hotel that doesn’t include breakfast, parking and a pool. We just don’t compromise on those three things. Those are our three must-haves and it delivered.

Activities in Islamorada

Robbie’s Marina

Our first stop on the Keys was Robbie’s Marina to feed the tarpon. It was a huge hit, not least for the fact that we bought about six shirts with the name “Robbie” on them. My husband’s name is Rob and he is known as Robbie, so he loved it.

The place was super fun with lots of great photo opportunities; there’s a dock and a snack shack, restaurants, and bars. We ate shaved ice and hand fed the tarpon, which was a thrill. They appear by the hundreds and hang around the marina docks waiting for visitors to toss them some fish snacks.

We’ll go snorkeling the next time we come here, but they also organize fishing trips as well. My suggestion is to plan a little extra time here to linger, have a snow cone, and peruse the stores.

Turtle Hospital

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My tip for a visit to the Turtle Hospital in Islamorada is plan ahead and make reservations. We arrived Easter week and saw other people were trying to get on the tours, which were sold out for five days in advance. We were really glad we had planned this stop, since our eight year-old son really enjoyed it.

The hospital opened its doors 1986 with goals to rehabilitate injured sea turtles, return them to their natural habitat, educate through outreach programs, and work toward environmental legislation making the beaches and water safe and clean for sea turtles.

They’re doing a great job – some of the turtles you meet are permanent residents and others are waiting to be released. They are all so precious and sweet, and our kid loved being able to observe them at touching distance.

Theater Of The Sea

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This was the big hit of our stay. Theater of the Sea is the ultimate antidote to the massive theme park experience, and feels like a flashback to 1950s. It’s intimate and personal and charming. We were able to get close to many of the animals, and you really feel as if they care about the experience you have here.

The park is one of the oldest marine mammal facilities in the world and was opened in 1946 by the P.F. McKenney family. They still own and operate it today, and I think that’s their secret—it’s a family run business with a lot of heart and history.

It’s home to Atlantic bottlenose dolphins, California sea lions, sea turtles, tropical and game fish, sharks, stingrays, crocodiles, alligators, and birds. Twelve million gallons of ocean water are pumped in daily to supply water to the three-acre natural saltwater lagoons, and while some of the animals here are rescued, many have been born here.

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My son got the biggest treat of his life when he landed a ticket to do their dolphin swim. My husband and I wanted to do it as well, but there were no tickets left as it was high season. Jett held onto the dolphin’s fin and was whizzed around the pool but this gentle, loving creature. It was wonderful to watch, and he’s still talking about it to this day. I got to kiss a dolphin during their show, so I didn’t do too badly either!

We also saw the parrot show and the sea lions, and did their 30-minute walking tour, which focuses on the education and conservation of sea turtles, sharks, rays, crocodiles, and raptors. Not seeing everything means that we have a good reason to return, but I would suggest you spend the whole day here. There’s a little beach area where you can have a snack or lunch. It’s small, intimate, and charming. We didn’t want to leave – we closed the place down, literally at lights off, they had to escort our three butts out the door.

Should You Take Your Family to the Florida Keys?

So are the Florida Keys family friendly? Yes, absolutely. Our lesson here was to always have a plan B. We encountered some inclement weather, which meant we weren’t able to get out on a glass-bottomed boat because of the winds, but we made the most of it. We reorganized our schedule and enjoyed our hotel for an extra couple of hours. No one can control nature, so you must always be flexible.

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My best advice for a visit to the Keys is don’t rush—it really is a place to linger. And however long you are planning to stay, stay an extra day or a week if you can find the time! And in high season plan, plan, plan and book, book, book ahead, or you will be disappointed.

We stayed during Easter and it was super busy, so the journey down there took us longer than the anticipated two hours. I would happily return again, but would aim to do it not on a holiday weekend.

But the beauty of the Keys is that you can forgive it anything because it’s so gorgeous. It was every bit as glorious as I remembered as a child, and it was a truly amazing place to share with my family. I highly recommend sharing the Florida Keys with your clan. It was a memorable, nature-filled family road trip. Click here to learn more.

For more articles about family-friendly travel from Margot Black, check out:

Text and Images by Margot Black for PeterGreenberg.com

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