With the warm weather year-round and the beautiful blue waters, the Florida Keys are a great option for a family vacation in Florida. The area is full of marine life, beaches, fishing and other water sports, making it perfect for either a relaxing or adventure-filled vacation. Whether you’re planning an Islamorada family vacation or are looking for more things to do in the Florida Keys with kids, we have you covered with this guide to the best vacation in the Florida Keys.
Disclaimer: Toddling Traveler participates in Amazon Affiliates and other affiliate programs. That means we may earn a commission for qualifying purchases through our links, at no charge to you.
Florida Keys Itinerary & Table of Contents
Florida Keys Itinerary: 7 Days or More
Below is a suggested itinerary for 1 week in the Florida Keys based on our most recent trip to the area. It includes 6 full days and 2 travel days and is the perfect mix of sightseeing and relaxation!
Day 1
- Fly to the Florida Keys via Key West and stop at Hogfish Bar & Grill for lunch
- Drive to Islamorada/ Pool Time
Day 2
- Morning at Anne’s Beach
- Lazy Days for Dinner by the beach & Feeding the Tarpon
Day 3
- Guys’ Fishing Excursion
- Robbie’s to shop and have brunch at the Hungry Tarpon
- Pool Time & dinner at home
Day 4
- Marathon Turtle Hospital
- Sunset & Dinner at Islamorada Fishing Company
- Florida Keys Brewing Co.
Day 5
- Morning at Theater of the Sea
- Parasailing from Robbie’s Marina
- Ice Cream at Key Largo Chocolates & Ice Cream
Day 6*
- Mangrove Kayaking Tour with Aquaholic Adventures
- Shopping at Bass Pro Shops and walk through Ernest Hemingway boat replica
- Lunch at Square Grouper
- Islamorada Brewery & Distillery
Day 7
- Florida Keys History & Discovery Center
- Brunch at Mangrove Mikes
- Naptime drive to Key West
- Check into The Reach Key West Resort
- Walk Around Key West, tour the Hemingway Home
- Dinner at Four Marlins & Ice Cream at Flamingo Crossing Key West
Day 8
- Sunrise walk in Key West
- Southernmost Point for a picture before the crowds
- Fly home from the Key West Airport
*Note: A lot of our family went to Bahia Honda State Park on Day 6, and it’s one of the best beaches in the Florida Keys. We opted to stay in Islamorada since we were driving past there to Key West the following day.
What are the Florida Keys?
The Florida Keys are a group of islands located in the southernmost tip of Florida in the US. There are thought to be about 1700 islands total and they span about 125 miles long. The Keys are connected by the Overseas Highway, starting just south of Miami all the way to Key West.
Although there are hundreds of Keys total, there are a handful of primary keys that most people visit for a Florida Keys vacation. They include:
- Key Largo– The most northern key, which is known for the Coral Reef State Park as well as fishing and other water sports.
- Islamorada– One of the most laid-back and non-commercialized keys. Just like Key Largo, it’s known for sportfishing and water activities. Robbie’s Marina and Theater of the Seas are two popular places to visit in Islamorada.
- Marathon– This key tends to feel the most commercialized, but it’s home to several marine research centers including the Dolphin Research Center and the Marathon Turtle Hospital.
- Big Pine & Lower Keys– This part of the Keys is less inhabited and includes the beautiful Bahia Honda Beaches and several other nature preserves. It’s a popular area for camping in the Florida Keys.
- Key West– The liveliest of the Keys, Key West is known for the bar scene on Duval and many great restaurants. It was also the home of many former greats (like Ernest Hemingway) who shaped our country’s history.
Where is the best place to visit in the Florida Keys? It depends on what you’re going for. Personally, we love Islamorada for a family vacation in the Florida Keys. It’s centrally located and packed with things to do while not feeling overly commercialized.
How to Get to the Florida Keys
Getting to the Florida Keys usually requires some combination of flying and driving (unless you’re doing a long road trip!) Key West International airport is a smaller airport that offers limited options for nonstop flights as well as several connecting flights. Depending on which part of the Keys you’re traveling to, Fort Lauderdale and Miami airports are also great options for flying to the Florida Keys. They both are larger airports and tend to offer more affordable flights.
Islamorada is in the central part of the Florida Keys, and it’s about the same distance to any of the 3 major airports. It’s about a 1.5 to 2-hour drive to Islamorada from either Fort Lauderdale, Miami or Key West airports.
Related Post: Flying with a Baby: Tips for Before, During & After Your Flight
The Overseas Highway (aka the Florida Keys highway) is very scenic and includes mile markers along the way. The mile markers in the Keys are an easy way to designate both location and distance. Islamorada, for example, is generally located from mile marker 91 to mile marker 73. If you’re looking to do a Florida Keys road trip, it’s a beautiful drive regardless of where you’re starting and ending.
Best Time of Year to Visit Florida Keys
Planning a Florida Keys family vacation and not sure when to go? Weather-wise, the best time to visit Florida Keys is typically in November to April when the weather isn’t typically as humid and rainy January and February tend to have the best prices- after the holidays and before Spring Break kicks in. Prices are always higher around the holidays and Spring Break, so it’s best to plan your Florida Keys vacation in advance.
My family prefers to visit the Florida Keys in February. The weather in the Florida Keys in February is typically warmer (high 70s/ low 80s F) but not too hot. Be sure to look for a Florida Keys rental home with a heated pool, just in case the weather isn’t consistently hot.
Florida Keys Vacation Rentals
Islamorada is a great area to stay in for its central location in the Florida Keys. If you’re visiting the Florida Keys for family vacation, I definitely recommend getting a rental home if you’re traveling with a larger group. We typically book home rentals through AirBnB, VRBO or Booking.com. There are a few differences between AirBnB and VRBO, but both have a great selection of options for house rentals in Islamorada. Keep in mind that house rentals in the Florida Keys can be a little tricky to find, since many vacation homes rent on a monthly basis.
We’ve stayed in a great 5-bedroom home in Lower Matecumbe Key in Islamorada for two trips to the Florida Keys. It’s ideal for a few families or a large group to share. If you’re visiting Islamorada with kids, it has a heated in-ground pool that’s amazing for swimming all day long. Note: It can be tough to find legal weekly house rentals in Islamorada. Be sure to book early and make sure the house you rent is approved for weekly rentals.
For a smaller condo style rental, Anglers Reef offers 2-bedroom condos in Islamorada.
For Islamorada, Florida house rentals on Booking.com, search here.
Looking for Family-Friendly Resorts in Islamorada?
If you’re looking for more of a resort setting in Islamorada, Islander Resort is centrally located with access to a beautiful private beach. (It’s also home to the Florida Keys Discovery Center.) Drop Anchor Resort and Post Card Inn offer reasonably priced accommodations with good reviews.
For more of a luxury family-friendly resort in the Florida Keys, Cheeca Lodge is a great option. It has several activities for families including a kids’ club, plus a spa and golf course as well. (We have not stayed there personally but my parents have a few times!)
For more Islamorada, Florida resorts and hotels, search here.
Things to Do in the Florida Keys
There are so many fun things to do in the Florida Keys regardless of where you stay. With Islamorada being centrally located, we love it as a home base for easy access to everything the Florida Keys has to offer. Whether you’re visiting the Florida Keys with kids or without, keep reading for fun things to do in Islamorada and the rest of the Keys.
Theater of the Sea
If you’re looking for a fun way to come up close to Florida’s marine life, Theater of the Sea should be on your list of things to do in Florida Keys with kids. Theater of the Sea is perfect for kids of any age, and it’s primarily made up of a few rotating marine life shows throughout the day. During both the sea lion and dolphin shows, kids are chosen to come up to the front and interact directly with the animals. There’s also a short, bottomless boat tour that goes around the property and offers a little more insight into Theater of the Sea’s conservation efforts.
Theater of the Sea is located at 84721 Overseas Hwy (Mile Marker 84.5) in Islamorada, FL.
Fishing Charters in Islamorada and Key Largo
Deep sea fishing in Islamorada, FL is one of the most popular things to do in Islamorada, FL. (In fact, it’s known as the Sportfishing Capital of the World!) The guys in our family have gone fishing a few times with Captain Larry Wren from First Choice Charters. He’s located at Whale Harbor Marina and is known as one of the best Key Largo and Islamorada fishing guides. Sailfish are the most popular fish around Islamorada, but we’ve also caught things like King Mackerel, Red Snapper and Grouper in the past.
We have also fished with Captain Casey from Sea Monkey Charters in the past. He’s another great choice if you’re looking for an Islamorada or Key Largo fishing charter, and he’s located at Baker’s Cay Resort marina.
Looking for Florida Keys boat rentals to go fishing on your own instead? Keys Watersports is one option for Islamorada, Florida boat rentals.
Feed the Tarpon at Robbie’s Marina in Islamorada
Many people know Robbie’s of Islamorada for the Tarpon (fish) feeding. The docks out back are filled with pelicans and tarpon fish everywhere you go. You pay a small fee to enter the docks, and then it’s an additional charge to purchase bait to feed the fish. Getting it to them before one of the nearby pelicans tries to snatch it from you is almost a game in itself!
There’s also an open-air market at Robbie’s with several local vendors. It’s a great place to look for handmade souvenirs, toys for the kids, paintings and more. Robbie’s also has a great restaurant on the water with live music.
Robbie’s of Islamorada is located at 77522 Overseas Highway (mile marker 77.5) in Islamorada, FL.
Parasail & Kayak in the Florida Keys
If you’re looking for a variety of watersports in the Florida Keys, Robbie’s Marina is also one of the best places for jet skis, parasailing or kayaking. It has quick access to calm waters, including the mangroves at Lignumvitae Key State Park.
If you’re looking for parasailing in Islamorada, Robbie’s is a great place to do it. We went parasailing with Sundance Parasailing out of Islamorada, and the views from above the water are amazing. (Keep in mind that children must be at least 6 years old to parasail.) You can also get jet ski rentals and go on snorkeling or sunset cruises from Robbie’s as well.
For mangrove tours in the Florida Keys, Aquaholic Adventures is another option. They offer paddle boarding and Kayaking in either Key Largo or Islamorada. In addition to mangrove tours, they also offer dolphin and sunset tours, and children of any age can kayak. Prefer to rent kayaks? They will deliver the kayaks or paddle boards to a destination of your choice.
Marathon Turtle Hospital
The Turtle Hospital in Marathon has been around for over 35 years, and it’s high on our list of animal experiences in the Florida Keys. It focuses on rehabilitating injured sea turtles and ideally returning them to their natural habitat. At any given time, there are dozens of turtles undergoing rehab at the Marathon Turtle Hospital, and there are also several “permanent residents.”
A visit to the Marathon Turtle Hospital includes an overview of the various factors (natural and man-made) that can harm turtles. The well-versed guides then take you around the property’s dozens of tanks to share more on the hospital’s efforts and each of the turtles. It’s engaging enough for children of all ages, and our kiddos loved learning more about the turtles. (Especially “Bubble Butt!”)
Visit the Florida Keys Beaches & State Parks
One thing that many visitors to the Keys don’t realize is that there aren’t a ton of large and sandy public Florida Key Beaches. (If you’re looking for white sand beaches, Siesta Key in Sarasota is the place for you!) Many rental properties and resorts in the Florida Keys are either beachfront or have access to a private beach.
Anne’s Beach is a small, sandy beach in Islamorada with free public access if you’re looking for a quick, easy beach trip. It offers a few hundred feet of boardwalk, restrooms and picnic facilities. It tends to be more of an exploring beach than a swimming beach, but the calm waters are great if you’re visiting Islamorada with toddlers.
For a true Florida beach experience, Bahia Honda State Park is home to some of the best beaches in the Florida Keys. The two primary beaches are Loggerhead Beach and Calusa Beach. It has bright blue water, lots of sand, and snorkeling opportunities along the coral reef. Bahia Honda is located in Big Pine Key, just south of Marathon.
Read more on state parks in the Florida Keys here.
Spend a Day in Key West
Key West is less than a 2 hour drive from Islamorada, so it’s totally doable for a day or quick overnight trip. One year we went on an overnight trip without the kids, and another year we spent time in Key West prior to flying home. 24 hours in Key West is never enough, and we look forward to spending more time there in the future!
If you’re staying overnight in Key West, La Concha Hotel & Spa is a great option right in the heart of Key West. The Reach is another option for a family-friendly resort in Key West right on the beach.
Some ideas for things to do in Key West include:
- Visit the Key West Butterfly & Nature Conservatory
- Explore the Ernest Hemingway House and find cats throughout the gardens
- Walk around Duval Street for shops and nightlife
- Get a photo at the Southernmost Point Buoy
- Walk up the lighthouse at the Lighthouse & Keeper’s Quarters
- Stop at Mattheessens Key West for a huge, yummy cookie sundae
- Search for the roosters everywhere you walk
For Key West excursions and more fun things to do in Key West, search here.
Places to Eat in Islamorada
The Florida Keys are known for fresh seafood and specialties like conch and key lime pie. Since we specifically spend a lot of time in Islamorada, we’ve included several great family-friendly places to eat in Islamorada as well. We love finding restaurants with outdoor dining, and Islamorada has so many great options with outdoor spaces that are perfect for kids.
Lazy Days
Known as one of the best restaurants in Islamorada, Lazy Days is great for families. They don’t take reservations, but there’s a sandy area to play outback and runaround while you wait for a table. The restaurant has a huge menu with a ton of fresh options for seafood in Islamorada. The restaurant has ample space with a number of indoor and outdoor seating areas. It’s one of few Islamorada restaurants on the beach, and it’s a great place to catch live music at night.
Pro Tip: You can also feed the Tarpon fish at the pier out back. Just ask for a bag of fish chum at the fish market stand to feed them. We even saw two nurse sharks on our last trip there.
Islamorada Fishing Company
The waterfront setting and live music was my favorite thing about the Islamorada Fish Company. We usually go there to take advantage of the bring your own fish preparation after a day of fishing. Since Islamorada is known as a fishing town, many of the restaurants let you bring your own fish to prepare it for a group- family style with several side dishes. The Islamorada Fish Company is also connected to the Bass Pro Shop in Islamorada, which is an attraction in itself.
Morada Bay Beach Cafe
If you’re looking for a more upscale cafe in Islamorada, Morada Bay Beach Cafe is a great lunch spot right on the beach. My Beach Cafe Salad with ahi tuna was super fresh, and I recommend the Ketel Beachside to drink. It’s right on the beach and has a great sandy area for the kids to run around as well. Morada Bay is also known for the monthly (adults only) full moon party right on the beach, and it’s a filming spot for the TV show Bloodlines.
Florida Keys Breweries
If you’re looking for some great, family-friendly breweries in the Florida Keys, there are two breweries in Islamorada with great outdoor spaces. Islamorada Brewery & Distillery has several unique beers on draft as well as yummy cocktails. (The Pineapple Kickin’ Mule made with Islamorada Vodka is SO good!) They also have a food truck and a fun outdoor beer garden that’s great for kids.
Florida Keys Brewing Co. is also located in Islamorada. They offer tons of different beers on draft and a vibrant outdoor beer garden. There are also food trucks at Florida Keys Brewing Co. almost daily.
Both breweries are also great venues for live music in Islamorada.
Breakfast in Islamorada
If you’re looking for a great breakfast place in Islamorada, there are several options to choose from. We included some of the best breakfast places in the Florida Keys below.
- Mangrove Mike’s is hands down one of the best places for breakfast in Islamorada. It’s a small place with more of a diner vibe, and it gets pretty crowded on the weekends. The menu is huge, and one of our favorite dishes to share is the French Toast sampler. (Three of us shared it and it was definitely more than enough!)
- Hungry Tarpon at Robbie’s Marina is awesome for an outdoor breakfast or brunch in Islamorada. The lobster frittata is delicious, and if you have Bloody Mary’s they have one of the best in the Keys.
- Lorelei’s is another great option if you’re looking for breakfast in Islamorada by the water. The food is good (not great,) but you can’t go wrong with sitting by the water. It’s also a popular place for happy hour in Islamorada, and it’s a great casual option for any meal of the day.
- Midway Cafe is known for serving the original key lime pie, and it also has great breakfast. They offer a variety of pastries, breakfast sandwiches and specialty coffees in a cute cafe setting.
- Bayside Gourmet is another place that’s known for having some of the best breakfast in Islamorada. Schedules haven’t aligned for us to try it yet, but it’s on our list for a future visit to the Florida Keys!
- Islamorada Coffee Roasters doesn’t technically serve breakfast, but it’s one of the only organic, fair trade coffee roasters in Islamorada and the surrounding Keys. If you’re looking for some of the best coffee in the Florida Keys, it’s worth the stop!
Have you been to Islamorada or the Florida Keys? Please share in the comments if you have any favorite places to eat or fun things to do in the Florida Keys!
Related Posts:
- 8 Awesome Things to do at Siesta Key, FL
- 7+ Fun Things to Do with Kids in Sarasota
- Family Vacation in North Myrtle Beach: Where to Stay, Play & Eat
- 50+ of the Best Things to Do in Ocean City, MD
Like this Post? Click to Pin for Later
Great post! Thank you so much for all the info. I am considering planning a family road trip from Miami to the Keys
Thank you, and you’re so welcome! Please let me know if you have any addition questions about your Florida Keys road trip : )
I have all of the Florida keys on my bucketlist!! Just gotta make the plans!!
We really love Islamorada if you ever get to the Florida Keys! It’s super laid back.
We drove through Islamorada on our way to Key West, we stopped for lunch but I really wish we had more time there. This post has really got me wanting to return!
It’s such a beautiful place. I hope you get to Islamorada in the future!
Can you tell which beach it is that has the bright colored chairs?
Hello! It’s called White Marlin Beach in Lower Matecumbe Key. It’s a community beach that’s technically private and accessible to the houses in that area. Most house rentals in near there will come with access to it.