If you’ve never checked out the Florida Keys you should! It’s super easy to get there, and you will be surprised to find how tropical and remote it feels when you arrive. Here’s our favorite tips & spots we love if you are looking to spend 3-5 days with toddlers to teenagers in the Islamorada, FL Keys area.
First, we find a direct flight into FLL or MIA. Upon landing (I try to not plan our drive south at rush hour) we pick up a rental car and head 2-2.5 hours south to Islamorada, FL. Recently I learned of the app Turo … it’s Airbnb-for-cars basically! Each time I’ve used it, I’ve picked up the car from the short-term parking garage at the airport which is a breeze at check-out time!!! This past trip we stopped at Snapper’s in Key Largo, FL. for a DELICIOUS hogfish meal and continued to Cheeca Lodge. In the past we have stayed in Ft. Lauderdale at the beginning of the trip and then made our way to the Keys. Either way, I do always enjoy a brief stay near the waves!! Thinking it’s probably best to do first… relaxing in the Keys and then going to the mainland can feel extreme 😎
Photos above are from Cheeca Lodge and our favorite room (king bed in private bedroom, mini bar area perfect for my electric skillet & tea pot … gives us all plenty of space)
Where we like to stay:
Marriott Key Largo - almost the first destination as you land upon Key Largo. This property is great, in that it offers room-service, has on-site bar and restaurant and also offers pool, bay swimming and more activities for the kids (shuffleboard, foosball, volleyball, water activities/boats, sand toys, etc). I don’t love how some of the room doors are motel style and face the highway (road noise) & while waterfront it faces east (no sunset) and doesn’t have a very spacious beach area.
Largo Mar, Key Largo, FL – Voted BEST SEATING!!! (by me) Largo Mar is another Marriott Property and very beautiful. You begin with very fun swing chairs in the lobby and end outdoors with a beautiful pool deck and beach area to include chairs in the water! Great beach facing property with pool, water access and all the amenities!
We enjoy the Islamorada area the BEST, so our first choice is: Cheeca Lodge, Islamorada, FL – Cheeca has history dating back until the 1800’s! Lots of pictures in the lobby hallway to catch you up! It’s a great property for EVERYONE, offering an adult pool, 2 family pools (one with more shade than the other) and beach front seating and access. There is LOTS to offer that’s already included for kids – bikes, fishing rods (bait extra$), non-motorized watercraft, ping pong, air hockey, x-box, board games, golfing, tennis and more! The tiger roll at the sushi restaurant, Nikai, is AMAZING!
Great sunset spots include:
Snapper’s Bayside, Key Largo, FL – great cocktails & seafood with a view … there’s also a fun boat that departs from this dock that you can charter to take you on a cocktail cruise!
Islamorada Fish Company, Islamorada, FL - the Cheeca shuttle can deliver you if you don’t feel like driving the 2 minutes it is! Beautiful sunset views and great viewing of the tarpon, nurse sharks, manatees and more from the surrounding docks. This restaurant is owned by Bass Pro Shops. The store next door is the place to get all your boating outfits!
Morada Bay & Pierre’s Restaurant, Islamorada, FL - take the Cheeca shuttle again! (Kids have lots of room to run and play you can even bring a soccer or football … maybe even some dried rice or crackers for the assortment of wild chickens). If you are just in for cocktails (kids or no kids) Pierre’s has the most romantic back porch and seats for sunset and bonfire evenings…. Go watch the Netflix show Bloodline!!!
While there are no sandy beaches with waves to body surf, there is an amazing world to explore in a boat! We charter a fishing boat and head into the Florida Bay (no waves) and always enjoy all the wildlife … dolphins, turtles, manatees, many different types of sharks & fish. We have a GREAT back sea fishing captain so let me know if you’d like his contact details! Deep sea fishing is not good for anyone in our family, so we haven’t experienced it from this area BUT see lots of great success at the dock located at Post Card Inn.
While doing school from home spring of 2020 Ivan missed his turn to teach his classmates about him in person so we did even better! Video of his expertise. Not JUST casting but also catching fish WITHOUT bait!
Other places to visit:
CAUSAL BITE… Bad Boy Burrito, Islamorada (across the street from Cheeca, photo’s above) – order and while you wait for your FRESH & delish food take a walk behind the building and go check out the docks. Lots of water life and very cool boats to check out!
Robbies, Islamorada (4.7 miles south of Cheeca Lodge) – quite a unique stop indeed! Sit at the restaurant/bar on the water but BEWARE of the pelican’s on the dock!! Ivan got his finger bitten when trying to feed the tarpon. They sell fish so you can feed the fish, but the pelican’s want some too!! There are little shops with more local art and fun things to discover. Check out the LIVE WEBCAM HERE
(Mile) Marker 88 Restaurant (10 miles north of Cheeca Lodge) - Great spot to watch the sunset as you sit in the fun swing tables or bar side.
FUN ENTERTAINMENT FOR ALL AGES… Theatre by the Sea (2.8 miles north of Cheeca Lodge, photo’s below) – Family owned and operated, this is one of my FAVORITE spots in all of Ivan’s childhood! They have a rotation of shows so check the website. We like to get there when it opens and do the first round. Tends to be less crowded and the sun isn’t quite as HOT just yet!
SHOPPING… Shell World, Key Largo (16 miles north of Cheeca Lodge) – you can hit this spot on the way to or from Cheeca. You can pull into the LARGE store from US1 going either north or south. LOTS of fun souvenirs to discover.
Lots of area boutiques to explore all along just LOOK around as you drive
I do always enjoy a day or so near the airport to enjoy the waves and sandy beach. This trip we tried a new spot, Largo Mar on Ft. Lauderdale Beach. This spot has a great location on the beach and tons of activities for toddlers to teens (basketball, mini golf, shuffleboard, tennis, foosball, pool, swings & a playground as well as the pool & beach). Aside from the hotel failing to mention to us there was a marathon on the morning of our departure causing us to miss our flights, we enjoyed the location and amenities of this spot.
Don’t forget your sunscreen and to apply often!!! We learned that the hard way this trip 😎