Getting to travel a lot with our kids, we make an effort to be sure that each trip, big or small, has some meaningful elements to it, not just fun. We are extra lucky in that we get to visit the Florida Keys quite often and it’s a destination we’re really familiar with, so each trip we try a little more to find things that are unique to us or that will really enrich our travels. And that’s what I want to share today: how we take meaningful vacations in the Florida Keys.
Now, I know that not everyone goes on a trip and intends on staying busy or learning something, but we do, and sometimes that busy part is actually just busy on paper, but it’s intentional time spent together. We’ve put together our favorite, most meaningful things to do together in the Florida Keys in hopes of inspiring a different sort of trip you may want to take. Because it’s a place we visit so often, if you have any questions about planning a trip or the other things to do in the Keys, please leave a comment or send us a note. We’re always happy to share more and help YOU plan a great adventure!
Be sure to check out our Florida Keys website, TheKeysExplored.com!
What Makes the Florida Keys a Special Vacation Destination
I think what keeps bringing us back to the Florida Keys for family vacation is that as our kids have grown up they are able to do more and more of the interesting activities. They enjoy completely different things now than they used to and they have gotten adventurous, making each trip back a unique opportunity to try something new. Thinking back to our first trip, they were scared to jump into the water in the shallows for some light snorkeling, and now they’re jumping off boats above reefs and looking for sharks. We’ve gotten to see them change as people through our many adventures in the Florida Keys.
And of course the big thing that draws us back continually is the amazing weather. We live in Florida and are thankful for our endless summer, but also we get our cold spells up in St Augustine, so being able to visit the Keys and remember what 85 degrees feels like when we’ve been chilly is amazing. The climate of the Florida Keys is so different from the rest of the state, particularly November through March, so it’s always a place that revitalizes us. Our trips tend to come at just the right times for us too, usually after very busy stints, so the warmth and better attitudes is always good for us as a family.
When I think about what makes our time in the Keys memorable, it often does come back to being forced to chill out quite a bit. Even when we really schedule our trips and have tons of activities planned, either due to needing a break from the heat or because we’re on a boat going somewhere, we have to take time to just sit and be. That’s something a lot of people, us included, tend to miss out on when they’re taking vacations: time to just exist and chill. The Florida Keys are always great for that, and they know it. You’d be hard pressed to stop somewhere or stay somewhere and not have a hammock readily at your disposal. The vibes force us to mellow out together, and that makes for memorable time spent together.
Best Keys for Family Trips
Not every one of the Florida Keys is a destination that we’d be like “Yes, let’s spend several nights on Big Pine Key” or we aren’t like “One night on each key… GO!” Nah, we have places that we enjoy and that we know we can have lots of wonderful things to do or we can settle into a mellow relaxation pattern, which for our travels can be unique. For us, and I would say for most seasoned Florida Keys visitors, those places are Key Largo, Islamorada, Marathon and Key West. These are the most well known towns and also have the most options for hotels and resorts.
You can find some great little gems of inns and vacation rentals on the less well known Keys, and maybe that’s what you’re looking for, but that’s not typically how we like to plan a relaxing, meaningful trip together. I find that when we’re in a vacation rental or away from services and restaurants we end up with much more work to do, more coordination and planning, and it’s just not the vacation we hope for. We end up working like we’re at home or doing a lot of driving to be able to function each day. And that’s why we tend to stay in the more popular Florida Keys towns.
Key Largo – Easy Destination
I love staying in Key Largo because it’s where the local Floridians tend to go. It’s the first of the Florida Keys and is the closest to Miami or the Naples area, making it an easy getaway from the cities. What makes stain and Key Largo a special and more memorable sort of trip is that it’s proximity to the mainland makes it very easy to get there and enjoy without having to do a complete road trip through the keys, even though a Florida Keys Road Trip is one of the most fun things you can possibly do in the whole state.
Key Largo has some of our favorite restaurants, there are some State Park spaces and even a bird sanctuary that we visit each time we’re down. When it comes to the pace of Key Largo, on the day-to-day it is very chill, but on Fridays and Sundays it can be a bit much just because of all the traffic leaving or arriving in the Florida keys. I would say that’s the only downside to staying on Key Largo during your vacation is that everybody has to go through to get to wherever their final destination is.
Check out Key Largo resort options here
Islamorada – the Keys Like a Local
Gaw, I love when we get to stay on Islamorada. Even though it’s so close to Key Largo, Islamorada has a completely different vibe. This is where we go when we know that we have a few days to relax and maybe want to play out what it would be like if we actually got to live in the Florida Keys. I know that might sound like a weird thing to do, but when we come to Islamorada we go out for coffee and we go to the garden store and then we go swimming and snorkeling. Islamorada is, to me, what the Florida Keys dream is.
We’ve gotten to stay in some wonderful accommodations here as well. My number one favorite place to stay in Islamorada is the Casa Morada Resort, which in general is adults only, but since we’ve been before they’ve made an exception for us to stay as a family. And also because so many people are coming here and staying in larger resorts, there are some smaller boutique places to stay that are really incredible and overlooked. Whether you want to stay in a vintage roadside motel or on a houseboat, you can find it here and often for a better price than what you might expect for the Florida Keys.
See Islamorada hotel options here
Marathon – Relaxing Florida Keys
What makes Marathon such a good place to have a different sort of Florida Keys trip is actually the quiet of it. With Key Largo you have the people moving through, Islamorada has all the fun stuff and it’s pretty centralized, and then Marathon is a bit more detached. There are resorts and parks, but there’s not really a central area that draws people to one spot (except during the Seafood Festival). There’s the area where you’ll find the Marathon Sea Turtle Hospital, and you can ride your bike between resorts and restaurants, but it’s not chalked full of activities in one spot.
I like staying on Marathon when I know we get to have downtime at our resort hotel and when the goal of our trip is relaxation instead of action. Yes, there are lots of things to do on Marathon, but the way the island and community is set up, it’s more for enjoying the peace and quiet of the Keys instead of the adventure side of them… unless you’re into fishing, and then this is a great hub to be based out of.
Is Key West a Good Family Destination? – YES!
I know that Key West has a reputation for Fantasy Fest, the Hemingways and Pride celebrations, but none of that impacts the town as being a good family destination. When we stay in Key West we’re usually pretty busy because there are so many museums and water activities. Some of our favorite snorkeling and wildlife tours go out of Key West, which means we tend to stay busy. Having said that, we’ve gotten to enjoy so many trips here that we can now roll into town and just enjoy the vibes and visit our favorite spots.
If you’re planning your first trip to the Florida Keys and you want to make it memorable, spending at least two nights in Key West is a good idea, as you’ll get to enjoy the beautiful historic district, the chickens running around everywhere, and you have such easy access to some incredible tours and experiences. Key West is really the catch all for a bigger family trip too because you’ve got such diverse things to do and restaurants that multigenerational vacations are a breeze here. We’ve done them and love it!
Find a family-friendly Key West resort here
Special Things to Do for a Memorable Florida Keys Vacation
So now that we’re ready to plan what to do to make your Florida Keys vacation extra memorable, let’s think about what sort of experiences would be much different than a regular Keys trip. If it’s your first time, you can choose whatever activities work with your schedule and budget, but if you have been before and are trying to make this something new for you and your family, this is where you can consider what you’ve done and enjoyed in the past and what would make this upcoming trip different. I get it that a trip to the Keys is not a normal and consistent experience unless you actually live in Florida, and with that so many of us who live here tend to just repeat the plans we’ve done before. This is all of ours’ chance to do something new.
Unique Wildlife Experiences
I think it’s safe to say that unless you live in a rural location you maybe aren’t kayaking and exploring the wilderness all the time. I know a lot of city folks are great about weekend hiking and such, but if that’s not how you roll, this is a great opportunity to make your Florida Keys trip extra memorable. When you come to the Keys, you’ll be surrounded by water, and that water is full of wildlife. Even if you’re not a big fan of snorkeling, you’ve got lots of other ways to experience that myriad animals and birds and really level up the interest of everyone on your trip.
Of course I love doing kayak tours, but for us paddling is a normal thing, whether it’s around our waterways of St Augustine or when the manatees are in at Blue Spring State Park, but when we’re in the Florida Keys, there are some of the most beautiful and unique places to explore via kayak, and they’re full of wildlife. We’ve done night tours, kayak tours through the Key West National Wildlife Refuge, rented kayaks for established water trails… Each time we’re out on the water we get to see so many creatures that it keeps us coming back for more. While kayaking in the Florida Keys we’ve come across dolphins, spotted eagle rays, stingrays, sharks of different sorts, manatees, lots of amazing birds and some of the most beautiful views possible.
Kayaking isn’t for everyone, I get it, so if you need something different that will add the wildlife element to a Florida Keys vacation there are some really cool tours you can plan that don’t require any skills or are physically demanding. One of the most unique wildlife tours in the Keys is actually the glass bottom boat from John Pennekamp State Park out to the Molasses Reef. It’s amazing what you can see as the boat explores the reef system off Key Largo, and this is perfect for ANY visitor. It’s a really good all-ages activity that brings you to the wildlife and gets you out on the water. Book the Glass Bottom Boat tour here!
The other wildlife tour that’s amazing but is a bit more active is Danger Charters’ sailing trips or Key West Eco Tours’ Java Cat. It’s a mix of sailing and swimming paired with amazing birdwatching and exploring the sandbars of Key West. It’s a beautiful trip and will make for a memorable family experience. Book Danger Charters sailing here!
Dolphin Encounters – Responsible Tourism Options
For the longest time I’ve always been very against any sort of dolphin tourism that included human interaction, no matter the establishment or the type of interaction. I’ve since learned a lot about both dolphins and the facilities in the Florida Keys that work with them, and I have a different view now. While I’m not saying that all dolphin experiences are done in a way that’s respectful to the animals or in their best interest, there are some dolphin facilities in the Florida Keys that are involved in both rescue and conservation, and that’s what I would encourage you to consider. Getting to interact with dolphins is very special and memorable, and definitely something to consider if it’s in your budget.
We got to spend a day at Dolphin Life Key Largo and it was eye-opening. Whenever we’re at a sanctuary or aquarium I always ask really direct questions about the animals and facilities, and here at Dolphin Life that led us to learning about voluntary action in training dolphins, as well as dolphin rescue work and the marine mammal hospital operations. Our whole family learned a lot, but what was most memorable was how we got to interact with the dolphins in the water. Book a Dolphin Life experience here
A dolphin swim is such a unique experience, and each one is different. Because at Dolphin Life Key Largo the dolphins are trained with voluntary action and positive reinforcement, each swim is different and depends on what the animals are feeling inclined to do. For us it meant that we got a lot of time hanging out in the water with Jet and Tug (the dolphins) and them just checking us out and letting us play with them and hug them and such. The curiosity they showed us and their desire to make eye contact was amazing. I would absolutely come back here to Dolphin Life Key Largo again and again.
Other notable options with similar training programs/approaches and conservation work include Dolphins Plus (Key Largo) and the Dolphin Research Center (Marathon). There are other dolphin swim options, but I am not the informed expert on their facilities and practices so I cannot directly recommend.
Group Sandbar Trips
The Florida Keys really are beautiful, and even if you’ve been here fifteen times and driven the Overseas Highway more times than you can count, the sandbars you pass are just amazing. And you know, if you want to have an unforgettable day that’s just 100% Florida Keys and chill, you need a sandbar day on your vacation. You can do it on a budget or you can be fancy, but adding a group sandbar trip is a must. There are a few ways to do this, so depending on how big your group is and what everyone’s activity level is, you have some different options.
The prettiest sandbar in the Florida Keys is the Grassy Key / Valhalla Sandbar off the northern end of Marathon, just past Curry Hammock State Park. You can charter a boat from Marathon or Duck Key if you want to visit with just your group, or you can go out with the Marathon Mermaid on their awesome catamaran and have an incredible day. Spending several hours on the water is such a great baptism into Florida Keys life, but also knowing that so many people come down here with a fear of too much sun, choosing Marathon Mermaid with its huge covered area is a great option for groups. You can easily derail a whole vacation by one or two people getting badly sunburned or sun-sick at the beginning of your trip, so make a thoughtful decision when you’re planning a sandbar day like this. Book the Marathon Mermaid here
For smaller groups, you can plan a more tailored sandbar trip with a charter, and you don’t have to just consider this one sandbar in the Middle Keys. One of the best day trips we’ve ever done in the Florida Keys was out of Key West with Island to Island Charters where we got to enjoy lots of stops at different sandbars, and we got to navigate through mangrove islands and go dolphin watching, all at our own behest. We did something very similar with Lazy Dog Adventures, also in Key West, with some added kayaking and SUP time to our trip. Getting to experience the backwaters of the Florida Keys as a family is a special sort of travel memory, and worth carving out time and budget for. Book Island to Island sandbar charter here OR Book Lazy Dog 1/2 day sandbar here
Family Resort Time
Since we do talk so much about all of the fun things to do and activities that make a Florida Keys trip so special and memorable, we can’t forget to include downtime together. This is something that I personally struggle with because I want to be on the go and having all the experiences and adventures possible. I can say with certainty that when you’re planning a family vacation, especially one that includes either your extended family or the grandparents, not everyone wants to be on the move all the time. After years of traveling a ton, with and without our extended family, I’ve had to learn to enjoy downtime and allow everyone time to relax on their own.
Family resort time is a luxury because it means that you’ve got enough time to do and see the things you want AND you have extra time to let it all be absorbed. Feeling rushed and exhausted has become such a part of how we often travel that when we carve out time with just “hang out at resort” as the goal, we enjoy it so much. The Florida Keys have lots of resort hotels that are great for families and that make it easy to enjoy pool days or just relaxing in the shade reading. These days you squirrel away without “big plans” end up being some of the best, most memorable, especially for the kids on the trip, so don’t discount the option of just chilling out together.
When you’re planning your trip and choosing where you want to spend the most time, look at what resorts and hotels are going to off your group the best options for downtime together. The Blue Flamingo Resort in Key West is our favorite family-friendly hotel in the Florida Keys and we’ve stayed there three times. In the Middle Keys, Hawks Cay Resort is great for having lots of options for activities onsite and they’ve got a variety of accommodations. Bakers Cay Resort on Key Largo is wonderful for pool time, beach time and activities on property. Really though, there are so many choices, just be sure to research before booking.
I hope you feel like you’ve got some good ideas for planning a unique Florida Keys vacation. I really doesn’t have to be all Jimmy Buffet and sportfishing, but can be meaningful, memorable and fit for all kinds of interests in your family. Use our ideas for the different activities we add to our travel to see what can make your trip a little more fun and special. If you have any questions about planning a trip to the Florida Keys, please leave a comment or send us a note. We’re always happy to share more and help others have awesome trips to this beautiful place.
