Florida Keys:

What you need to know:

  1. We’ve visited numerous places in Florida and have enjoyed both coasts.  Based on our experience, the Florida Keys provides an ambiance that is very different than the rest of the state.  The laid back island atmosphere is very reminiscent of the Caribbean.  It’s like a Jimmy Buffet song everywhere you look.
  2. The Florida Keys are beautiful.  The shades of blue in the sea make any activity near the water very enjoyable.  However, the Florida Keys are not known for their beaches.  They do have them and they are pleasant but if wide swaths of sand and long beach walks are what you expect, you should change your mindset.  You go to the Florida Keys for great activities, great boating/fishing, great views, and great seafood.  
  3. In Miami, you’ll likely see numerous expensive boutiques, fancy cars, high rises, and impeccably stylish people.  In the Florida Keys, you’ll likely see numerous pick-up trucks, marinas, baseball caps, and bait shops.  
  4. Key West is the biggest city in the Keys and is definitely the busiest and most expensive area.  We’ve never experienced Key West nightlife but we’re told it can get pretty wild.  However, we had a great time there with the family during the day and highly recommend a visit.  
  5. One tricky thing about the Florida Keys is the waves.  You’ll likely be planning an activity that involves being on the water and wave height can impact how enjoyable that is.  Unfortunately, it’s really hard to forecast wave height in the Keys so it makes sense to have a plan B in place for the day’s activity in case the swells are too big.    


8-night itinerary for a party of four in the Florida Keys (2 adults, 2 kids ages 10 and 6)

Thought Process:  I could sit in a chair with a book and a drink staring at Caribbean blue water all-day, every day.  But our kids get bored, even at all-inclusive resorts.  So we need to be in a place with some great adventures that we’ll all enjoy.  Thankfully, the Florida Keys fits the bill.  If you follow this itinerary, you’ll have plenty of opportunities to make some wonderful memories.  

Where you’ll stay:  Marathon is centrally located in the Florida Keys, approximately an hour north of Key West and 2.5 hours south of Miami.  There is an extensive list of things to do in the area and the scenery is wonderful.  Check out vrbo.com or Airbnb.com to find a rental property that will work well for your family.  Make sure it’s a property with numerous positive reviews.  If you appreciate a well maintained beach and your party is not more than 4 people, you should consider staying at Sea Isle Condominiums in Key Colony Beach.  

How you’ll get there:  There are numerous ways to get to the Keys.  Flying into Key West is probably the easiest way but it’s also the most expensive usually.  Flying into Miami, Fort Lauderdale, or even Jupiter can be a lot cheaper.  If you follow this itinerary, you’re probably going to want to rent a car.  

Day by Day

Day 1:  Fly into your chosen airport, pick-up the rental car that you reserved ahead of time, and head to the property you rented.  Unload the car and go pick up some groceries.  

Day 2: Relax at the pool/beach/dock.  It’s highly likely that the place you are renting either has a pool, dock, or private beach access.  The day after and before traveling is a great opportunity to relax and enjoy the amenities of the property.  There will likely be lizards/crabs for the kids to chase around and plenty of sun for you to enjoy.  If the place you are renting has a dock, inquire ahead of time about whether or not there will be fishing poles available for you to use.  If not, consider mailing yours out ahead of time or seeing if you can get a reduced rental rate for buying and leaving some there for future guests.  If you don’t feel like cleaning and cooking your catch yourself, numerous restaurants in the area will do it for you.  If you’re in need of a beach and your property doesn’t have one, make your way over to Bahia Honda State Park.  If you need a pool, then head over to Sunset Bar and Grille, one of our favorite places in the Keys, which we’ll touch on later.  

Day 3: Fury Ultimate Adventure or the Dolphin Research Center.  If your kids are strong, high energy daredevils, then the Fury Ultimate Adventure (not to be confused with their other tours/packages) is definitely worth considering.  During this six hour adrenaline rush, you will drive to Key West where you’ll get to jet-ski, parasail, snorkel, and enjoy an inflatable playground all while sailing around on a catamaran.  If your family is more low-key, consider a trip to Marathon’s Dolphin Research Center to get up close and personal with the resident wild life.  

Day 4: Aquarium Encounters.  If you like swimming with and touching sea life, this is the place for you!  Note that the various encounters do all have their own prices but there are exhibits included with general admission.    

Day 5: Visit Key West.  You may have been to Key West already in route to the Fury Ultimate Adventure, but you likely didn’t have the time or energy to properly enjoy it.  Visit the southern-most point in the continental United States.  Take some time to appreciate the blissful simplicity and hands-on experiences at the Key West Aquarium or the Key West Butterfly and Nature Conservancy. Get educated at the Florida Keys Eco-Discovery Center.  If you’ve never been to a Ripley’s Believe it or Not, here’s a chance for another first.  That said, just walking around Key West and enjoying the shops, cafes, and chickens is a great experience too.

Day 6: Go Snorkeling.  There are plenty of snorkeling tours available in Marathon that will either take you out to a reef or the mangroves depending on ocean conditions.  You may have already done some snorkeling with Fury, but the nice thing about going out of Marathon is that the mangrove option is available if the ocean is too choppy for the reef so you don’t have to worry about rough seas.  That said, there is much more sea life out on the reef.  If you are an experienced boater and have your own snorkel gear, it is very easy and economical to rent a boat in Marathon, pack a picnic lunch and a dive flag (available for purchase at dive shops), and head out to Sombrero Reef or wherever else you would like to visit. However, if you have your own snorkel gear and enjoy getting a great bang for your buck, take your dive flag over to the park/parking lot just to the right/east of Island Fish Company and the Mile Marker 54 Boat Ramp.  Here you will find a very solid, free, walk-in snorkeling spot for kids and beginners.  The area has its own parking where locals often congregate to watch the sunset.  Go to the curved rock wall that reaches out into the sea and from shore you will see schools of parrotfish and other marine life.  The area is identified here on Google Maps as “Fishing SPOT.” Enter the water by the kayak(?) ramp and snorkel the northern edge of the rock wall.  In addition to numerous parrotfish, we saw a bunch of lobsters, a nurse shark, and plenty of little colorful fish.   Just make sure one of you has a dive flag tied to your ankle in case a police boat drives by (as they did when we were there).  Consider purchasing some inflatable snorkel vests if you don’t have some already although the area is shallow.  

Day 7: Go kayaking with Dave at Marathon Kayak.  This will depend on the energy level of your family, but I’ve been told great things about kayaking with Dave.  We had to cancel our original reservation so I haven’t experienced this first hand but people rave about the experience.  Once again, the weather may determine whether or not you kayak in the ocean or the mangroves, with the ocean option providing more opportunity for hands-on wildlife experiences.  

Day 8:  Relax at the pool/beach/dock again.  By this point, you have done a lot.  So before you head home, take some more time to relax and enjoy the tranquility of this beautiful locale!

Note 1:  We don’t normally recommend restaurants because there are plenty of other sites that do it better.  However, you absolutely must visit Sunset Bar & Grille for at least one meal.  The place is more of a destination in our opinion because it is right on the water and has live music and a bunch of tailgate games on the property.  Best of all, there is a huge swimming pool that all of the kids play together in until 10pm every night.  So you get to sit back for a couple hours and enjoy great music/food/drinks/view while the kids entertain themselves in the pool.  It’s a beautiful thing.  Either get there early or be prepared to walk around the property for a while before you are seated.  

Note 2:  There are plenty more activities in the Florida Keys than what we have listed here so there are ample opportunities for substitutions on the itinerary.  We all got to experience riding in a helicopter for the first time on our last visit as well as parasailing but both are pricey and can be done at other locales.  You may want to consider visiting the turtle hospital during your stay but know that you do not get to touch the turtles.  Of course, fishing is a big deal in the Florida Keys and there are many opportunities to do that whether it be via a charter, renting a boat, or fishing from shore.  You can rent jet-skis as well but know that there are height requirements and the child must always ride in back of you.