Logistics for this mega bike ride weren’t as difficult as you may think. The chosen path is The Florida Keys Overseas Heritage Trail, which makes it easy for you to get from Key Largo to Key West in 100ish miles. Renting bikes from Key Largo Bikes also makes this trip a breeze.
Day 1 – Key Largo to Islamorada – 25miles of pedaling
Arrived in Miami and took an uber to bike shop in Key Largo (approx 1 hour). Got the bikes and were off! I booked our accommodations for each night so we could just leisurely pedal and stop wherever we wanted knowing we already had a place to stay. We started with breakfast at a Cuban restaurant near the bike shop (it was ok). Peacocks roamed freely in some areas and were so beautiful! Made a pit stop at the Islamorada Beer Company to have a few drinks and made our way to Robbie’s, which was cute but felt a little touristy. Stopped at Anne’s Beach to put our feet in the water and rest before we made our way to our home for the night.
We stayed at a cute little place, Lime Tree Bay Resort, that had a restaurant where we also had dinner. The food was good as was the key lime pie. The goal was to have key lime pie everywhere we went so we could judge who had the best. At the resort right when I was thinking to get in the water I saw a 3ft shark. That urge to get in the water quickly passed.
Something to note if you make this trek in the summer is the weather. It’s Florida so it’s obviously hot and muggy, however, we had some sun but mostly overcast weather and rain, which are not my ideal conditions, but for this trip it was perfect! The trail has a lot of exposure so you could easily get fried. Bring plenty of water because some stretches there’s not a ton of places to stop. This was the first trip where we didn’t have a home base and had to bring all of our stuff with us. It was no biggy, we travel light anyway.
Day 2 – Islamorada to Big Pine Key – 45ish miles of pedaling
After a little breakfast at the resort it was time to hop back on the hogs to the next destination. I saw a 6ft shark in the water below the bridge. Sharks really do live in the ocean, huh? We stopped for lunch at Island Fish Company where we had an excellent view. It was raining pretty heavy so I was happy to stop. From about this point on I wore my homemade poncho, which is nothing more than a trash bag, and not the first trip I’ve had to do this. Hallelujah for the poncho and sombrero which made the rain bearable! We also stopped at Herbie’s Bar & Chowder House for beer, conch fritters and key lime pie.
Island Fish Co. – Crab cakes & tacos 
Herbie’s 
Conch fritters & key lime pie at Herbie’s 
We continued to pedal to Keys News & Coffee and shortly after made friends with a man fishing. He didn’t speak English, but we were able to communicate and had a few laughs with trying to get the coconuts down from the tree. More pedaling to Bahia Honda State Park. It was absolutely beautiful here. Shortly after this stop FD shimmied up a tree and got 3 coconuts! We enjoyed 1 of them roadside and continued on to our lodging on Big Pine Key. We stayed in a camper that I found on Airbnb. This particular section of the keys doesn’t have a lot of lodging options, however, our camper was nice and new and out in the middle of nowhere. For dinner we biked to the next key and ate at Boondocks Grille (not impressed at all).
Day 3 – Big Pine Key to Key West – 30ish miles of pedaling
Started with coffee at 7 Mile Cafe & Kava Bar and off to our final destination of Key West for a few days! Today was a bit rainier than the others, and the poncho and sombrero were still my friends. We did our usual of stopping to swim, eat, and the like. While the trip was very relaxing and fun, the last 8 miles wore on me mentally. With the rain and soreness from the bike I was ready to get to Key West. The stop at Baby’s Coffee lived up to all the hype I had read prior to taking this trip. The bagel, the coffee, the friends we made, were all amazing!
We finally arrived to our bed & breakfast at the Southermost Point Guest House and it was just the cutest! After a quick swim in the pool we took a walk down Duval Street and then had lunch at the Seaside Cafe. Shortly after it was back on the bikes to explore Key West. At this point it was 100 and sunny so biking was the only way to explore. We consumed more key lime pie at Kermit’s and lounged at our bed & breakfast. The grounds here were so pretty and the porch was perfect for sitting.
The food at Conch Republic was delicious, but the beer at Waterfront Brewery was better. So good it was worth a second trip. On the way back from dinner there was a complete down pour and we flew on those bikes! It was a total white wash. I’ve never pedaled so fast.
Day 4 – Lounging – still pedaled around Key West
Right near the b&b there was the most amazing Cuban restaurant called Ana’s Cafe. The breakfast, coffee, and smoothies were all so delicious. We came back a few times. After sitting on the beach for awhile it was time to get back on the hogs and explore. There aren’t a ton of beaches on Key West, but Smather’s Beach is the largest (and very pretty). We ran into a friend we met at Baby’s Coffee a few days earlier and she recommended we try Rams Head Southernmost. It did not disappoint and had a great lively ambiance! Definitely try the stuffed avocados. Key lime pie was also delicious.
The next morning for breakfast we ventured to Moondog Cafe since Ana’s was closed. We had fish benedict (amazing) and key lime pie. My favorite key lime pie from the trip was from….Moondog Cafe! It was slightly different than all the others we had.
It was time to leave the bikes and head back home. The nice thing about this bike shop is that you rent them in Key Largo but can leave them in Key West and they will come pick them up.
There are many keys that make up the Florida Keys with each one being different. Some are sleepy and then there is Key West, which is very lively. Biking was definitely the best way to experience them all. From the peacocks, deer, roosters, and sharks there was a lot of wildlife to be seen and a lot of good food to be consumed. I would highly recommend this trail system and the nice thing is that the trail is relatively flat with the exception of a few bridges. Yes, there are tons of bridges to cross too. Sometimes you are on the side of the road other times just on the path. I would not hesitate to say anyone can do this ride.
