The Ultimate 8-Day Florida Keys Itinerary: Marathon, Islamorada & Key West for Families
- paigelandrum
- Jul 7
- 10 min read
If you're dreaming of turquoise water, fresh seafood, unforgettable sunsets, and a vacation that feels worlds away without needing a passport, the Florida Keys should be at the top of your list. My family and I recently visited the Florida Keys and stayed in Marathon- it offers the perfect mix of relaxation, family-friendly attractions, and a central location that makes it easy to explore both the northern and southern keys.
This 8-day Florida Keys itinerary is exactly how I planned a week in the Keys. It combines iconic attractions with local favorites, plenty of downtime, and restaurants that are absolutely worth adding to your list.
A little background on our trip: I traveled with my husband and two daughters, ages 3 and 5. We went with another family of 4, who also had young kids. We went from Saturday - Saturday, and we brought a boat with us. We rented a house and did a mix of cooking ourselves, eating out, and take-out to bring back home.
Why Staying in Marathon was a Great Choice for Us
Marathon gives you easy access to everything while avoiding much of the traffic and crowds you'll find farther south. You're about an hour from both Key West and Islamorada, and surrounded by beautiful beaches, marinas, and wildlife experiences.
Day One: Arrive in Marathon
The drive down the Overseas Highway is one of the highlights of the trip, so don't rush it and take it all in. Pull over at scenic overlooks, admire the endless blue water, and start settling into island time before you even arrive.
We decided to drive the (allegedly) 8 hours and 45 minutes since we had a lot to bring with us for the week. We left at 4 am and after stops we arrived in Marathon just before 2 pm.
After checking into our rental, we went to Publix, where BOGO deals and the iconic "pubsub" are king. This grocery store has the freshest produce (IMO), a great meat selection, subs from the deli that simply can't be beat, and a dedicated liquor store for adult beverages. They also have a pharmacy (we were traveling with young kids, so you already know we had to utilize them!).
We spent the afternoon enjoying the pool, but some other great activities for night one include spending the afternoon at Sombrero Beach, one of the nicest beaches in the Florida Keys. The calm water, soft sand, playground, and picnic areas make it ideal for families.
Looking for a little adventure? Walk or bike part of the Old Seven Mile Bridge and visit Pigeon Key. Pigeon Key can only be accessed by boat or you can take the trolley, which travels on the old bridge. This is such a fun and unique experience!
For dinner, head to Burdines Waterfront. Their burgers are famous, the fish sandwiches are excellent, and the rooftop deck overlooks Boot Key Harbor. It's the perfect first-night dinner.
After dinner, take a walk over to Sunset Park and enjoy your first Keys sunset.
Day Two: Marine Life Adventures
Today's itinerary is all about experiencing what makes Marathon unique.
Start your morning at Florida Keys Aquarium Encounters, where you can feed stingrays, watch sharks, and even participate in interactive marine experiences. While this aquarium is outdoors, it does offer ample shade, which was much appreciated with the high temps we had during our week stay. I also recommend getting the feeding punch card - for $15, we were able to feed 6 different animals of our choice. Plan for 1-2 hours here to see and do everything. I recommend going early to beat the heat of the afternoon.
If you finish the aquarium and want another dose of marine life, check out The Turtle Hospital. This is a fan favorite attraction because you get to see rescued sea turtles while learning about conservation efforts.
For lunch, stop at Keys Fisheries. If you've heard of the famous Lobster Reuben, this is where you'll find it. Even if lobster isn't your thing, the seafood is incredibly fresh, and the waterfront seating makes it even better.
Consider spending the afternoon exploring Curry Hammock State Park.
Full disclosure - As a native Floridian, I am a big fan of Florida State Parks, and will almost always recommend them over going other places to get a feel for the "real" Florida. There are 10 Florida State Parks in the Keys and they are all unique and special in their own way.
For dinner, check out Lazy Days South, where you'll find excellent fresh seafood, waterfront views, and one of the best sunsets in Marathon.
Day Three: Fishing, Shopping, and Sun
A day for everyone! My husband opted to fish on the boat most of this day, while I took my daughters shopping. We mostly spent our time checking out the traditional touristy shops, but anywhere that I can window shop is my happy place.
Our favorite shop was Surf Style, which is about the size of a Target and has everything you could dream of - clothes for the family, shoes, fishing gear, beach necessities, toys, and then we get into the real surprises - an ice cream bar, candy bar, and the surfing simulator FlowRider (YES, like on the cruise ships!!).
This was truly so fun, I went back for more on day seven!
For dinner, check out Castaway Waterfront Restaurant & Sushi Bar, one of Marathon's local favorites for fresh seafood and sushi.
Day Four: Explore Islamorada
Today, head north toward Islamorada. Your first stop should absolutely be Robbie's Marina.
Feeding the giant tarpon has become one of the most iconic Florida Keys experiences, and watching these fish launch completely out of the water is something everyone remembers. Once you've fed the tarpon browse the market, grab a snow cone, or stay for a meal - the restaurant at Robbie's serves breakfast, lunch, and dinner. We made it in time for breakfast, and my kids absolutely devoured the fresh basket of donut holes that were brought as an appetizer.
Afterward, spend time browsing the local shops around Islamorada, and don't skip Rain Barrel Village. You can also check out the Florida Keys History and Discovery Center - we skipped this one to make it back to Marathon's Urgent Care before they closed (because kids), but hoping to make it on our next trip.
If you have dolphin lovers in your family, check out the Theater of the Seas- you can even swim with the dolphins!
The Florida Keys Brewing Company is another great stop with colorful designs, cold drinks, and a great way to relax while taking in the island scenery. This brewery is kid friendly and offers plenty of room for kids to roam and explore.
Another great stop for a meal is Lorelei Restaurant & Cabana Bar. The waterfront location is beautiful, and it's one of the best places to enjoy lunch while watching boats come and go. If you're looking for a sweet treat before driving back, stop by Midway Café & Coffee Bar for one of their homemade cinnamon rolls.
Day Five: Snorkeling and Sandbar Fun
We had a boat with us for this trip and chose to spend this day snorkeling at Sombrero Key Reef and then enjoying time at the sandbar. While I am no stranger to hanging out at sandbars, the water here is like nothing else. The blue-ness is just absolutely breathtaking, even miles offshore.
A last-minute decision, but I booked family photos with a local photographer for this evening, and it was so worth it! We met Julie at Isla Bella, a beautiful resort with a restaurant that is open to the public, and they are everything I could have imagined. Golden hour photos on the water will never not be a favorite.
After photos we ate at Sunset Grille & Raw Bar, located right beside the Seven Mile Bridge. The views alone make this restaurant worth visiting, and as a bonus, they have a pool! It was kind of wild to see people walking into the restaurant with towels and ready to go for a dip, but when in Rome I suppose.
Day Six: Spend the Day in Key West
We left early to maximize our time in Key West. We started the day at the Southern Most Point, which is a must do at least once, in my opinion. There was a line, but it moves pretty quickly - this actually gives you time to make friends with someone in line so they'll take a picture of your entire group.
After the photo op, we walked to the Hemmingway House, where we saw six-toe cats all through the property (my cat-loving 5-year-old was ecstatic). We then climbed the Key West Lighthouse, which made me a lot more nervous and took about double the time as it should, with two small kids. We skipped the Key West Butterfly & Nature Conservatory, but this is also in the area, and a fun activity to check out. Maybe next trip for us!
We then drove to the Mallory Square area where other attractions include the Key West Aquarium, Duval Street, ShipWreck Museum, Truman Little White House, and the Historic Seaport. This was only about a mile away from the other attractions we did earlier in the day, but it was pushing 100 degrees so we opted to drive and pay to re-park.
For lunch, you should grab Cuban sandwiches from Two Friends Patio Restaurant or enjoy seafood at Half Shell Raw Bar.
No trip to Key West is complete without Key Lime Pie. I recommend trying it from Blue Heaven or Kermit's Key Lime Shoppe and deciding for yourself which one reigns supreme.
Stay for the famous Mallory Square Sunset Celebration before making the drive back to Marathon (we didn't make it... because kids... but I've heard it's beautiful). I've also heard people clap at the sunset - not sure if this one is true, but someone let me know!
We visited during the Key Lime Festival, which is a week-long festival with activities each day, which was a fun twist. I'm a big Key Lime Pie fan, and a sucker for quirky merchandise, so of course we are not lacking in the souvenir department.
PS: did you know fried Key Lime Pie exists??
Day Seven: Slow Down
One of my favorite vacation tips is to leave room for absolutely nothing. Spend your last full day enjoying your resort pool, kayaking, paddleboarding, fishing, or simply reading a book by the water.
Families looking for another beach day should spend the day at Bahia Honda State Park, which many consider to be one of Florida's most beautiful beaches. If fishing is more your style, today is also the perfect day to book a half-day fishing charter.
By day seven, we were feeling the sun(burn) and had caught all the fish we could stand, so this day we spent enjoying our own backyard's amenities including the pool, games, and outdoor kitchen for our own fresh cooked meal.
Since this was our last night in #vacamode, we let the kids eat dessert for dinner. We went to Sweet Savannah's and it was the cutest ice cream shop with a gift shop built in. The best part was they had a play area in the back with ice cream toys and arcade games- the kids played for easily an hour while we sat and enjoyed the ice cream and atmosphere. This will be a place we will return in the future!
Day Eight: One Last Morning
Before heading home, enjoy breakfast at Wooden Spoon, one of Marathon's most beloved breakfast spots. Take one final walk along the marina, grab coffee, and soak in those last ocean views before making the drive back up the Overseas Highway.
You'll already be planning your next visit before you reach the mainland, I know I was.
Add Grand Tortugas to Your Next Florida Keys Bucket List
One place that stayed on my bucket list this trip was Dry Tortugas National Park, and it's already at the top of my list for next time. Since we were traveling with young kids, we decided to save it for a future visit because it makes for a long day and requires planning well in advance.
Located about 70 miles west of Key West, Dry Tortugas is one of the most remote and beautiful national parks in the United States. You can only get there by booking the Yankee Freedom III ferry or by taking a seaplane from Key West. Both options often sell out weeks ahead, so it's definitely something you'll want to reserve as soon as you know your travel dates.
Once you arrive, you'll find crystal-clear turquoise water, incredible snorkeling right off the beach, abundant marine life, and the impressive Fort Jefferson, a massive 19th-century coastal fortress that's one of the largest masonry forts ever built in the United States. You can spend the day swimming, snorkeling, exploring the fort, birdwatching, enjoying a picnic lunch, or simply soaking in the untouched beauty of this unique island paradise.
While it wasn't the right fit for our family this time around, I have no doubt it'll be one of the highlights of our next Florida Keys vacation, and if you're traveling with older kids or adults, I'd absolutely consider adding it to your itinerary.
My Favorite Restaurants in the Keys
If you're wondering where to eat during your Florida Keys vacation, these are restaurants I recommend over and over:
Marathon
Burdines Waterfront
Keys Fisheries
Lazy Days South
Castaway Waterfront Restaurant
Sunset Grille & Raw Bar
Wooden Spoon
Islamorada
Lorelei Restaurant
Midway Café
Marker 88
Morada Bay Beach Café
Key West
Blue Heaven
Half Shell Raw Bar
Two Friends Patio Restaurant
El Meson de Pepe
Kermit's Key Lime Shoppe
Frequently Asked Questions
Is Marathon or Key West better for families?
I recommend Marathon for families because it's quieter, offers easier parking, has beautiful beaches, and makes an excellent home base for exploring the Keys. With that said, my husband and I are already planning an adult-only trip back to Key West, likely for a long weekend. There was a lot we could not do with the kids.
How many days do you need in the Florida Keys?
I felt that six full days (plus two travel days), gave us enough time to enjoy Marathon while taking day trips to both Islamorada and Key West without feeling rushed. I do not feel like we did everything that we could have, so another trip will happen in the future.
Is the drive to Key West worth it?
Absolutely. The Overseas Highway is one of the most scenic drives in the United States, and Key West makes for an easy and memorable day trip from Marathon. Actually, when my kids asked what my favorite part of the Key West day was, my answer was the scenic drive!
Let Us Plan Your Perfect Florida Keys Vacation
One of the beauties of working with A Mouse and a Travel Company is that we can take all of the planning and research off of your plate.
Maybe you love the idea of the Florida Keys but don't know where to stay. Maybe you aren't sure which attractions are actually worth your time, or you're trying to balance beach days with activities your kids will love. Maybe, like us, you will be going with a group and trying to balance everyone's needs.
That's where A Mouse and a Beach's Select Services come in. When working with our Select Services advisors, we will build a personalized day-by-day travel plan designed specifically for your family. From restaurant recommendations and hidden gems to activity timing, driving routes, and local favorites, we will create an itinerary that lets you spend less time researching and just jumping to the good stuff.
Every trip is customized around your family's travel style, interests, and pace because no two vacations should look exactly alike. For example, did you know the Keys have their own All-Inclusive Resort in Key Largo? We recently visited, and can't wait to share more about this resort with our clients!
If you're ready to plan your own trip to the Florida Keys (or elsewhere!), we would love to help you create an itinerary that feels effortless from the moment you cross the first bridge into paradise. You can start here.
AMAAB Travel Advisor and Toddler Mom