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Florida Keys Reloaded – The Things We Always Wanted To Do

Updated: Nov 7, 2023

How to make lifelong memories in the Florida Keys, living your best life!

Do all the fun stuff 🌟🐠🏝🌊

This is our left-over wish list of things we didn't get to do when we were here in the summer - we came back in December and made it happen. If you are hoping to have one amazing trip, combine both for your everything Keys adventure.

Do I even need to sell you on this one? The drive from Miami to Key West, truly is one of the greatest road trips in the world, with 113 miles of scenic ocean views. The colors of the water are calling my name as I type this, and because I've seen this color, I love this place.

Our summer trip to the Key’s was cut a little short due to a hurricane threat. While later downgraded to tropical storm, we had already proactively made plans to leave a little early. There were some unaccomplished things on my bucket list, and I was ready to get back down there. But really, we were there July 4th weekend, and so was everyone else. We underestimated the volume of visitors and didn’t make reservations anywhere. We suffered for that also, so this time…. We had a better plan! A great itinerary…. A little planning ahead goes a long way.

Who knew the Florida Key’s was a perfect Christmas get away? Perfect weather? Almost 10 degrees warmer than my home in Brevard County, with it’s warm in the day, cool in the night conditions. Even when it’s cool it’s still warmer than anything else in driving distance! The winter wonderland of Key West was a great backdrop for building our Christmas adventure. Now don't get me wrong those pop-up wind and rains can be inconvenient, but you are still in a tropical paradise with a great view!

I had just come off of a Saint Augustine adventure, and loved seeing that historical city lit up to impress. To read about Saint Augustine. click here. I believe it is 2nd only to New York’s Christmas spirit. For more on New York at Christmas time, click here. I do love to travel during holidays!

The planning of this trip was very spontaneous. One week prior, we were talking in my kitchen with some family friends and it came up that one of them, Dylan, had never been to the keys. We live 3 hours North of Miami, and had been there on several occasions together. I was surprised and said “Oh we need to plan a trip”.

No wasted time here.

Never been? I feel responsible to fix that problem.

Dylan and Shannon are timeshare owners at Blue Green Resorts. The way this works for them is each year they get a certain amount of points and then assign these points to a vacation time/ place of their choosing. There are resorts all over the world they partner with, and 9 locations in Florida. The Florida Keys spot is the Hammocks at Marathon. Shannon was able to (very last minute) score one studio room, and a one bedroom, making our 3-day, 2-night trip a reality. This resort is also available for non time share use! And I'd stay there again.

I love to travel with my 4 kids and for years we’ve been doing road trips. But this was a very special road trip. My granddaughter’s first road trip. 3-month-old Nasali made the journey with us, and I couldn’t be happier with how it turned out. Of course, the rest of the group are grown and follow my schedules (for the most part) so this requires a little extra patience. As soon as our rooms were booked, I decided to make this part of our Christmas. Dec. 22 – Dec 24 seemed like a great time to share quality family time. And I adjusted the expense mentally, making a budget knowing some of our goals.


A note about traveling with babies: They are a part of the family and I encourage you to start early. Get them out of the house and it will be easier when they are used to your travel pace and style. Don't keep them in the house for 3 years then take them to a theme park and expect them to know how to act! Start small, start close to home, and build. Children need patience and your guidance now will go a loooong way!

On the road again! We're off!

** underlined items link to that site, for your convenience **

Objectives: I've learned the most important thing when traveling is to know what you want to get out of it. I usually spend a little time asking myself what I need from a trip. Peace? Adventure? Exploration? Then I go find things to best suit that need. I also check with those I'm traveling with. What are their needs/ goals for this excursion?

Going down this time was really easy to make goals since we had recently visited, and we really wanted to do the things we missed on our previous trip. Luckily, our traveling buddies were happy to let me make the plans!

This is a 3 Day Itinerary, with the First and last days including Driving to and from.

Feel free to use any or all of these suggestions. I will post the list below.

We had 3 Goals: (From North to South)

#1. Kayak at John Pennekamp (Key Largo) – We will need our own kayaks for this, the rentals on site for a group as large as ours was steep. So, we loaded our kayaks in the back of Dylan’s truck and hoped to take the mangrove trail. (We've since purchased some inflatables and it's been easy to make the drive and water fun happen.)

John Pennekamp State Park is something I recommend experiencing regardless of having your own water vehicles or not. It is home to the only living coral reef in the United States and if you want to explore underwater, this is the place to go. What makes snorkeling or scuba diving different here is that you can dive to see “Christ of the Abyss” a nine-foot-tall underwater statue of Christ located in just 25 feet of water off the coast of Key Largo. Boats leave from John Pennekamp several times through out the day, and this is a really impressive!


Paddle Watercraft Rentals (per hour)

Canoes $30.00

Single Kayaks $20.00

Double Kayaks $25.00

Kayak - 4 hours or less

Single Kayaks $40.00

Double Kayaks $50.00

Kayak - 4 hours or more

Single Kayaks $45.00

Double Kayaks $55.00

Standard Paddle Board

Per Hour $25.00

4 hours or less $50.00

#2. Snorkel Alligator Reef – (off Islamorada)

I began researching who had the best charter or considering renting a boat for the experience. After lots of reviews I made a few conclusions. I have already done this prior, and I opted to stay with the baby while everyone else went out in the water. This decision was based on the weather, chilly (71) and windy with 2-foot swells, and the fact that at all times someone would have to refrain from snorkeling to stay with her. I’d prefer to be that person and not have to keep a person out of the water.

Why do you want to do this? Just under 5 miles from shore, a very aquatic with diverse marine life awaits under the old lighthouse. No there are no actual alligators, it’s named after a ship that wrecked nearby. You can not kayak or paddle here, you will need a boat or jet ski. Having a captain lead the way does make this trek easiest. The ecosystem that has grown under the lighthouse is incredible. So many fish, and even barracudas will be visible in the dives below the surface. You do not have to go deep to appreciate the marine world.

Here's a list of business that you can contact to gain access to the Reef:

1. Robbies (sometimes hit or miss)

*Be sure to check Groupon first to see if there are any savings options!

Rates average $40 - $50/ per person.

** Now if you are going to Islamorada, you really can't miss Robbies!

This hub of souvenir shops, places to eat and things to do features tarpon feeding.

Tarpon feeding is a unique experience. You buy a bucket of fish, and dangle them over the side of the pier until a tarpon jumps up and takes it. This is not as easy as it looks, and tarpon have sharp mouths.

We usually feed the tarpon and them compare our war scars for the rest of our trip just for fun, and it is exciting! Also a great place to grab a bite to eat, or a tropical drink.

#3. Rent scooters in Key West.


This was kind of the #1 agenda item, as my oldest son was so sad over summer when there wasn’t a single scooter anywhere on the Island to rent. Renting scooters as a group is a great experience and if you are traveling down to the area will add a great memory to your life. The benefit of this is all the free scooter parking! If you've been to Key West you know parking is a challenge and free parking is near impossible. The scooter solves that problem completely. In all our travels, I was surprised how fun this was. Top 5 things we’ve done together as a family.

Why? Key West is a busy little hub and best seen on foot, but it is also very spread out. The scooters are a fun way to get around and make the most of the scenery.

3. Sunshine Scooters * Our top pick

Most rentals must be made and picked up by 4:00, reserve ahead of time. These will run about $40/ single, $50/ double. Add $10.00 for insurance. There are hourly and daily rates.

Key Deer –

While those were our top 3 – we are avid nature lovers and wanted to see the endangered Key Deer in their natural habitat.

The endangered Key deer is the smallest subspecies of the North American white-tailed deer. They are the only large herbivore in the Florida Keys and can be found in every habitat, where they feed on dozens of native plants. Despite the absence of predators, Key deer retain the characteristic raising their tails when alarmed, revealing the white fur underneath. They live in the 20-25 islands in the lower Florida Keys, ranging from No Name and Big Pine Key westward to the Sugarloaf Keys. There is a refuge, which has limited access due to Covid, but the free roaming deer can be seen easily by driving through Big Pine Key, and carefully watching. They are friendly, and while it is not in their best interest to feed them or touch them (like manatees) they are so much fun to watch in the wild. We wanted to go see these creatures, and we were able to!

Food –

It wouldn’t be the Key’s without a great lobster roll, some conch, and key lime pie. We had a list of foods and stops to make our stomachs proud. However, as some of our excursions planned to be costly, we decided to have some meals prepared and to eat a few choice places.

We recommend:

*The Island Fish Company – Fat Deer Key

*Fogarty’s – Key West

*The Lobster Shack – Key West

*The Southern Most Key Lime Pie Shop

*The No Name Pub (Long Pine Key)

Our 3 Day Itinerary...

The day prior fill up the gas tank and load all the stuff into the car. All bags packed and organized.

Last minute items like ice, cooler, and toiletries will be added the day of.

I always get a good night sleep before a road trip. Driving is not for the weary!

Day 1: Pull out of the driveway at 8 am. (Leaving from Brevard County)

We drive all the way to Snapper Creek Service Plaza, which is south of Dural on the Florida Turnpike headed South. This pit stop is great for gassing up and using a clean rest room. There are a variety of foods if anyone needs anything.

Arrive at John Pennekamp by 1 PM.

*We had two hours planned for kayaks, but the weather was not cooperating. Windy overcast skies and a chilly morning made us skip the water and just walk around instead.

Next stop: Lunch at The Island Fish Co in Fat Deer Key

This waterfront restaurant feels like a courtyard of great views. If the weather turns bad, which it did, the outside seating quickly converts to a clear plastic lined sheltered setting, still outside but out of the elements. Each of us ordered a different meal, and they were all served hot and delicious with fresh ingredients.

Check in to the Hammocks at Marathon

Unload into rooms and make a grocery store run.

*While I bring a lot of food already marinating in coolers, somethings need to be picked up when you get there, We found Winn Dixie and Publix both right up the road.

** Here's the tricky part. It was a long drive down and the weather was unusually cold/ damp and a bit rainy. The hot tub was already full. We did have the pleasure of a full kitchen in our one-bedroom unit so I made a nice dinner (keeping costs low) Chicken, Ribs, Rice and Beans. We opted to settle in for the night afterwards and just snuggle in for the night. This was not the original plan, the City of Marathon had both a community center and a catholic church with Christmas village lights and appeal we had considered. In December it gets dark around 5:30 and the State Parks would have been too dark to see. No one complained about the early night.

Day 2:

Make Breakfast in the room

Up & Out early!

Drive up to Robbies for the snorkel boat out to Alligator Reef.

Be there by 9:30 for registration

Feed the tarpon while you wait

Lunch - Leftovers in the room

Drive down to Key West to get scooters by 4:30.

Stop in Big Pine Key to admire the deer.

Pick up Scooters - Sunshine Scooters

Mallory Square for sunset

Fogarty's for dinner

Ride Ride Ride

See the Southernmost point buoy, and US - 1 mile marker 0.

*** A week after we were here some dumb ass lit the buoy on fire! Remember to go see your local landmarks. It is easy to take the simple things for granted that somewhere in our hearts we love.

Day 3:

Breakfast in the room

Pack up/ Load cars

Do a little kayaking on the way out of the Keys

Pit stops on the way out to explore

Florida Everglades (Anhinga Trail)

Go Home!

A few missed opportunities.... There never is enough time... Have one more day?

Key West Faves: We didn't make it to the Hemmingway House or Butterfly Conservatory, both on my wish list. Everything closes at 5 with last entry at 4:30, so plan accordingly. Also, Hemmingway House is (no longer) cash only. My other favorite stop in that area is Zachary Taylor State Park. Explore the fort, hang at the beach, and snorkel out to a reef within swimming distance.

Tips/ Tricks:

* If this is a road trip come prepared. Bring an umbrella, a bathing suit, a hoodie, and sandals!

* Make some of your own meals to save $$ But definitely eat some of the local delicacy's!!

* Look up what time the sun sets and plan to arrive in Mallory Square at least an hour earlier. Leave time for parking and getting to the waterfront.

Weather changes, and you'll wish you had something you already own! Dress prepared for changes. I've had on a sweater in summer and a bathing suit in winter. I've carried an umbrella for nothing, and gotten soaked when there was no rain expected. The worst thing that happens in the Keys is the wind - which can prevent small crafts from launching or create difficulty for bikes and lighter vehicles.

What do I bring to the Keys?

Cooler stocked with your favorite drinks and snacks

Beach toy variety

First aid kit with your favorite bug spray or repellent is (I make an essential oil spray)

If you are set up to transport bikes this is a really fun way to get around

All you need to be away from home for your length of time

I bring a few games (uno or monopoly) for a rainy day.

You see many trucks/ utility vehicles loaded with kayaks, paddle boards, coolers, bikes, and fishing gear making that drive down Overseas Highway.

*When I am in and out of the sun, in and out of the water, and eating outside of home a lot my skin definitely gets weird. My favorite thing is this: The Face Lotion Bar. It keeps my skin from peeling from over exposure and clears up and bumps or redness I develop super-fast. My skin is very sensitive it's been a game changer for me!

Must Haves:

Snorkel (goggles at least), underwater camera or go pro, sun hat, sunscreen, after sun lotion, beach bag, beach towels, small bag for valuables, waterproof phone case, consider a floatation option - if you do drop a phone or camera in the water, it will sink pretty fast!

I like the essential oil "passed tense" which is good for spot treatment of bug bites or irritations from any environmental type skin issues. Allergy pills/ essential oils, dinner clothes.

The Scoop - Our Favorite Stops Along the Way....

Sombrero Beach (Marathon) - Our quick pit stop could have easily been a few hours. Volleyball nets, picnic pavilions, playground, grassy area, and of course - the beautiful beach! The weather was sunny and warm, we would have stayed longer if we had more time. They now have meters for paid parking - do not let this slip, parking tickets are $90.00!

Crane Creek Museum and Nature Trail (Marathon) -

Quick pit stop by the side of the road to see the old trail and a reference to Flagler's huge train project which was destroyed by a hurricane in 1925. The museum is a small circle, showcasing the native creatures that call the Key's home. We did not hike the trail. However, it looked like a hike we would have enjoyed.

Curry Hammock State Park (Marathon)-

The largest undeveloped parcel of land between Key Largo and Big Pine Key. This park protects large areas of mangrove swamp, rockland hammocks and seagrass beds essential to the Florida Keys ecosystem. My kids walked the shoreline and played in the crystal-clear water. They found some clay and played with it for hours. There is a great playground, clean new bathrooms, and awesome areas to paddle/ kayak.

Mallory Square - Sunset and Christmas lights (Key West)

See the sunset on a waterfront full of entertainers and vendors. The dramatic colorful sunsets are part of the lure to Key West. Surrounded by food and shopping there is such a variety of options available. Enjoy the fire dancers and magicians while you wait, after dark the area clears out pretty quickly.

Right around the marina corner is the Opal Key Resort & Marina, who decorates their property exquisitely. The colors of the sky along with their Christmas set up is a great photo op!

The Southern Most Buoy - As seen at night (Key West)

Now to appreciate this you have to stand on the corner during the day to watch the rushing Ocean rock by you! Found at the intersection of Whitehead and South Streets, this is an obligatory stop during your trip to Key West and an famed photo op, as well. The sign points out you are just 90 miles to Cuba, (even though it's more like 94) and you realize you are closer to another Country than to Miami!

Mile 0 - Have you ever counted the miles as you were driving? Or counted down?? (KeyWest) Don't forget your picture at the end of the road! US1 is the longest North - South road in the United States, traveling from Fort Kent, Maine all the way to this point in Key West! The 2,370 mile road ends here. Might as well mark the moment you see it :-)

Finding a good place to stay is tricky!!!


Such a fun resort well located and very well maintained!

While a time share itself is a monthly expenditure, if you are planning to travel it does have perks!

This place is open to the public when there is space, and we did get in just a week before.

Having a full kitchen was awesome. We also bought two instapots down to help with feeding so many quickly. The space was really nice. We are not typically in the room much when we are on vacation but the first night being a good night to stay in. We had over 700 square feet with the big master bedroom and the front room. The boys slept on the pull-out couch, I also had our blow up mattress, and there was more than enough space to spread out. Only negative - the counter space was pitiful. We made it work.

Beautiful grounds in a good location, I would visit the Hammocks again!

All in all this trip was a win!!

Affordability meter: 5/10

On a scale of 1-10 how affordable is this trip?

When considering the value and quality of this trip vs the cost, I find it to be average.

We could not have done this without the points that allowed our rooms to be covered!

We planned some excursions that I knew would be $50/ per person expense, and I told the kids on the way down this splurge was part of their Christmas. Rather than buy a bunch of "stuff" they were gifted experiences, and memories of quality time together as a family. Some of our food was very affordable, some average, and some high. The views here are free! Everywhere you look is a view point that is priceless. Especially the 7 mile bridge which is permanently engrained in my brain. Many of the State Parks were a car entry fee of $8.00 and if you buy a State Park Pass, and use it at least once a month it pays for itself many times over. Check that out HERE.

I do find the Keys a high-quality experience that can be realistically budgeted for and in the affordable range. Lots to see and do in a unique tropical setting that feels like a vacation. With out all of the excursions it is even more affordable, but like I said this was wrapped into a Christmas gift.

The best baby ever: Nasali's first road trip! She was a pleasure to have along.

This guy sure was happy we made it back home. Thank you to our friend Kenny who took good care of our Leo while we were away.


~~Stay positive and enjoy the road you are traveling.

~~Be flexible. My flexibility is tested every morning when I want to be out faster than all the crew, we take a little time to gain momentum, but I know once we are in motion we stay in motion!

~~I love a good list and plan, but just as much I love being in the moment and just pulling over to see something! I will say on this trip I slept a little longer than usual, probably because of some really comfy beds mixed with the need to recuperate from a stressful school semester ending. Teacher fatigue is a real thing! That's why we need to plan these beautiful breaks!

~~Put the people above the things. People remember details, stuff does not.

~~Create amazing memories to look back on joyfully!

~~If driving, bring a good variety of clothing for the seasons. If flying, one sweater or hoodie and a few options for summer attire will be best.

~~It's usually 10 degrees warmer in the Keys than in Central Florida. But warm does not mean sunny, dry, or windless.

~~Bring the sneakers too. You'll be glad.

~~Sunhats and snorkels are definitely the vibe here.

I'd love to hear of your experience in the Florida Keys! Feel free to leave feedback and share your tips as well.

Mz. Savvy

May all your travels bring you back to your soul with love ♥🌞

Come travel with me!

Join our Yoga & Art Retreat in July 2024 Majestically Montana!

A budget self love adventure, where we will create Zen together in a BEAUTIFUL scenic location!

A note from the editor:

The information in this article was accurate when published but may change without notice. Confirm details when planning your trip.

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I specialize in helping families spend more time enjoying their quality time together and less time having to figure it all out. My four children have been my test subjects of how to plan a great family adventure for many years and now that my youngest is 18, many of my travels are work related, or grandma related! As time has changed, I've evolved but I still LOVE TO TRAVEL, explore, wander, visit, discover, learn and love. If nature is there, I can find my happy place. I use the term single not to emphasize my status but to signify that if I can manage some family fun on a limited teacher's salary with four children, anyone can do it. I am just very intentional in how I spend my time and earnings. I typically seek out budget friendly ways to enjoy my time, but will occasionally splurge for the right reasons :-)

Happy Travels!!

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Apr 07
Rated 5 out of 5 stars.

Loved your Florida Keys "travel guide". It is better than "Moon Florida Keys" which I just bought for our up coming trip. Of course, I will use both, but really enjoyed all of your suggestions. Thank you so much....Jan R.


Such a great get a way trip!! This was so much fun and you did great organizing. Thank you ❤️

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