Exploring the Florida Keys with a Toddler

March 7, 2019

The Florida Keys has been a dream destination of my husband for years. I actually hadn’t really heard of the Keys and didn’t understand why he was always talking about wanting to go. I am happy to report the Keys did not disappoint! We stayed for two weeks and ever since we left Tim find a way to sneak into the conversation, “We could always go back to the Keys…

There are several “keys” with the furthest one being the most famous, Key West. After a lot of research we chose to stay in Big Pine Key which was a halfway point so it would be a more central location for visiting the different Keys. We stayed at Sunshine Key RV Resort which is one of two RV Resorts offered through the Thousand Trails & Encore club. The resort was fantastic. We wish we’d paid a little extra for a waterfront site. And the water in the Keys is so shallow we wouldn’t have to worry about Evelyn wanting to wade in.

**Side Note for anyone reading this who is or planning to be full time RVers. We bought our Thousand Trails & Encore membership the weekend of Thanksgiving scoring a great deal on Black Friday. The TT membership + Encore (which seems to have the really nice RV resorts) was about $1,000. You also have to pay $50 per region. So obv. that’s a lot. The benefit is for the next year we can stay at any TT campground (and there are tons) for FREE and Encore locations are $20 a night. As a full timer, we will more than make our money back. Also, every place in the Keys is at a minimum $100 a night. So we would have spent the same just to stay for the two weeks. Instead, we gained a membership that will allow us to stay at some amazing places for free or $20 a night for the next year. The only thing we are kicking ourselves about is that we didn’t purchase sooner. Their biggest areas are the East Coast, West Coast and FL. Pretty much everywhere we already stayed on the East Coast for the last 6 months had at least 1 TT campground. So we’ve easily spent $2,000 in accommodations that if we had the membership we wouldn’t have spent.

Unfortunately, as of winter 2019 a lot of the RV Resorts are still rebuilding due to a bad hurricane season. In fact, unbeknownst to us at the time, we seriously scored getting a spot at Sunshine because it had just re-opended. While they’ve done a great job bringing the resort back up to par there were a few signs of the storm like the beach area and the water was a bit murky. There’s a boat launch on the property where you can spot manatees. And they have a beautiful walkway out to the ocean and secluded swimming spot. We walked there with Evelyn in her stroller for her nap and then parked her on the dock while we took a dip. *Another side note, the current was INSANE, Tim had swam away from the dock to get his empty beer can that flew into the water due to some wind. It ended up sweeping him out and he legitimately almost drowned. I’ve been meaning to call them to let them know they need to add a life ring on that dock…Moving along, there’s also an oyster shucking and fish cleaning table and gorgeous pools.

My head is spinning from everything we did and i’m trying to think of the best way to communicate it all. So I think i’ll just organize my thoughts by days and the locations.


The first place we explored was Bahia Honda State Park. It was an easy drive from our location and has a ton of offerings. We snagged a picnic table on the sand for all of our crap and spent the day with E playing in the sand and water. The water is shallow with no waves which was perfect for a toddler. They offer kayak rentals and snorkeling tours. There’s also a cafe and store (with free WIFI!) with anything you may have forgotten and there’s a science building with interactive displays for little kids. They’ll have activities planned at certain times like feeding turtles, etc. There’s also a walk you can take up to a bridge that’s no longer in use for a gorgeous view. We did this during E’s nap.

KEY WEST – Day 1

The next day we headed into Key West. There’s a lot to see but it isn’t a large area so we parked the truck and explored on bicycle. There’s probably an equal amount of bicyclists to cars on the road so as a biking newbie I felt really comfortable and wasn’t worried about our safety. Finding parking can be really hard so I would actually recommend renting a bike. It was great because it was easy to stop or take a detour whenever we wanted while exploring the main strip of Duval Street – tons of great shops!

We visited the “Southernmost Point of the Continental US.” The line was INSANE. So instead we hopped on this rock wall and asked someone to take our photo because no way E was going to wait in that heat. There’s food stands right nearby with coconut water and popsicles. Next we biked to Lagerheads Beach Bar and Grill and we LOVED it. Small shop, female owned, tables on the sand with lounge chairs and a beach area. E was able to play with rocks and sand. They also have corn hole and other games and the bean bags kept her occupied while we enjoyed local beer and fish tacos. There’s also a water sport vendor that shares the beach area so if you wanted to rent a kayak or water bike you could do that too.

We spent the rest of the afternoon biking up and down Duval Street and poking into some shops – and then quickly exiting with a fussy toddler.

Thanks to a fellow RV-er we stayed for the big event of the year – the Parade of Boat Lights (Dec 15) – tons of boats all decked out in festive lights, sail around the docks. Festive music and families with little ones in Christmas pajamas. We grabbed dinner to go at Garbo’s Grill which is a taco & burger food truck (SO FREAKING GOOD). I got a Yum Yum Shrimp Burrito and Tim got a Korean BBQ Burrito – make sure to grab a TON of napkins!! Then we walked back to the waterfront to have a front row seat to the parade. Downtown Key West is also OPEN CONTAINER and for the show there were street bartenders. We got beers for less from a corner store. We ended the night with a Key Lime Pie (which I didn’t realize originated in Key West but of course I get it now) and it was so good! The two famous spots are Kermit’s Key West Bakery and Key West key Lime Pie, Kermit’s is a little cheaper so we went there and I thought it was fantastic.


The next day, we headed out to an island which came highly recommended from some retirees at the park. We could get to it via kayak from our RV resort. I thought Tim was crazy to want to kayak in the open ocean with Evelyn. However, it turned out to be super comical. It was probably about 2 miles out into the ocean but it was so shallow the entire way that twice our kayak bottomed out and Tim had to get out and drag us into deeper water.

When we got to the island there were a few other boats there and some dogs. The beach is really nice. There’s a rope swing and a beautiful display of shells. The water was calm and it was one of our highlights of the trip for sure.


The next day we headed to Sombrero Beach on Marathon Key to kayak through some mangroves. Using google earth, Tim navigated us and it was really cool and also comical as we got quite stuck as they became very narrow. We have an inflatable kayak but there was also a vendor right there on the beach and you could rent. The beach has a large playground area as well. We met some French Canadians and a little girl who only spoke French and played with her (mon petite ami!) and it was so fun! I also wish we spoke French, it just sounds glorious but I digress..

On the road coming into Sombrero was a huge stretch of gorgeous new rental town homes. A lot had pools on the property and were also waterfront. If you aren’t an RVer, I would look into this area for sure. (Coco Plum, Vacation Rental, 305-390-2315, Reel Sombrero – I have no idea the price but I took a photo w/ all the info because if we ever come back with family we would def look into this place!)

KEY WEST – Day 2

The next day we headed back into Key West to explore Truman Waterfront Park Amphitheater. There was a splash pad that I had my eye on for E. It was great but whoever designed this wasn’t a parent (I’m finding this more and more as we travel the playgrounds and splashpads across the country). First, there were stairs (stairs and water for a KIDS splash pad is the WORST idea). Then there was this large mushroom that aggressively dropped water and terrified every single child on the splash pad. Furthermore, there was this slide that had a HUGE water drop, every child that got up there would start freaking out and several parents had to run in and get completely soaked to grab their child that was frozen in terror. If a child did go down the slide, it was too slick and they would skid on the ground. But otherwise- it was great! There’s a large playground next to it and we easily spent two hours here between the playground and the splash pad.

For lunch, we stopped a vibrant hole-in-the-wall, Frita’s, for their Frita Confundita (burger topped with onion, frita sauce, mojo pork, caribbean slaw, and crispy fried house julienne potatoes on a freshly-backed Cuban roll) which they are known for. It did NOT disappoint. I also grabbed a cuban coffee to get me through the rest of the day.

We unfortunately had a few bad weather days and weren’t able to get to everything we wanted to. Below are a few other places we wanted to get to but didn’t get the chance:

Dry Tortugas National Park – Take a ferry for a day trip (you can also primitive camp overnight). This looks AMAZING but the ferry is 2.5 hours each way and didn’t make sense with E and her nap schedule. If you have older kids, or no kids, DO IT! The snorkeling looked so cool!!!

Dry Tortugas National Park is in the Gulf of Mexico, west of Key West, Florida. It comprises 7 islands, plus protected coral reefs. Garden Key is home to beaches and the 19th-century Fort Jefferson. Loggerhead Key has a lighthouse and sea turtles. On nearby Loggerhead Reef, the Windjammer Wreck, the remains of an 1875 ship, is a popular dive site. Bush Key is a nesting site for seabirds like sooty terns.

A tour of Ernest Hemingway’s home – located in downtown Key West. Too expensive and E was too much of a flight risk for us to even attempt going. There’s also Truman’s Little White House.

The Harry S Truman Little White House in Key West, Florida was the winter White House for President Harry S Truman for 175 days during 11 visits.

John pennecamp coral reef state park – for snorkeling

Fort Zachary Taylor Historic State Park

Fort Taylor predates the Civil War and is a National Historic Monument housing the largest cache of Civil War armament in the world. Beyond its historical importance, the park is the southernmost state park in the continental United States.

A rum tour at Papa’s Pilar Rum

If you go, let me know and send me pictures of your travels!! Mamas, put this one on your bucket list for sure!

Xo & Sunshine,