Overseas Highway Route US-1 Roadtrip Stops + Key West Favorites

The drive from Miami to Key West is one of the most iconic in the USA and a route I drove many times from going to school in Tampa. The amount of time it takes to get there can be unpredictable on the two-lane road but there’s PLENTY to do to make the journey as enjoyable as the destination. Here are my best recs starting in Miami and traveling south.

Feed the Tarpon at Islamorada Fish Co
Many videos of people feeding tarpon in the Keys are at Robbie’s in Islamorada. There’s a better “secret” stop that many people bypass to go here. Behind the Bass Pro Shops/ Islamorada Fish Co, there is a bait shack on a dock that sells frozen bags of shrimp. Park at Bass Pro, buy a bag out back, and walk the dock through the restaurant to feed the tarpon. Bonus: in the winter you are very likely to see manatee here with the tarpon.

Go Fishing on a Party Boat
The keys are one of the BEST places to fish in the United States because you don’t have to take a boat miles and miles into the ocean to find quality fishing. If you have little fishing experience and don’t want to spend $1,000+ on a private sport charter, the Marathon Lady is a great party boat option. (WATCH our day on the Marathon Lady).

See Alligators & Deer in Big Pine Key
We stayed for a week here one year to do some extreme fishing and what we discovered were some overly friendly neighbors with antlers! These small key deer are running around everywhere on Big Pine Key. One route to find them is by following your map to Blue Hole Observation Deck where you will also likely see alligators, especially at night. Note: there is a big fine for feeding these deer. Don’t do it!

Stop by Flipper’s Former Home at the Dolphin Research Center
You may be more familiar with the DCR than you realize as it was one of the filming locations for Flipper! It’s a little old school and overall not a ton to see, but one of my favorite things about this place is that the dolphins are not in tanks. They are in the ocean water with barricades. Some of the dolphins are so old they just lay on their sides all day and the caretakers have to put sunscreen on them.

Once you arrive in Key West, here are some must-visit places:

Blue Heaven
Blue Heaven is the epitome of Key West dining, known for their meringue pie and chickens that run around your feet. The food is great and the brunch line will be LONG. This is also my favorite spot to grab some colorful Key West merch. They have t-shirts and sweatshirts here that are cuter than any tourist traps on Duval!

Hemingway House
I would say 30% of people visit this iconic home for the Ernest Hemingway history and the other 70% visit for the cats. Personally, I am in the first part. This is one of the most gorgeous Florida properties with beautiful tiled bathrooms and Key West’s first in-ground pool. The property is stunning. So why come for the cats? Well, there’s not many places you will find a clutter of six-toed kitties!

(WATCH Blue Heaven & Hemingway House with me and the Wright Sisters)

Kermit’s
Finding the best key lime pie in Key West is overwhelming (WATCH the Wright Sisters and my review). I’ve tried just about every popular key lime pie in Key West, including the Publix grocery pie which is shockingly one of the best key lime pies in the USA. My personal favorite that is Key West exclusive is the frozen Kermit’s Key Lime Pie on a stick dipped in chocolate. It’s fun to eat and nobody else does one like it! Also worth trying: any key lime pie labeled “extra tart.”

Sloppy Joe’s
I’ve never had a sloppy Joe here and I’m not even sure if they serve them, but it sure does get sloppy! This bar has deep rooted Key West history, most iconically known for being a Hemingway haunt. We spent Christmas day here one year and the atmosphere was a blast. This is also another iconic spot to grab some Key West merchandise!

DJ’s Clam Shack
Regular readers know I’m a real Girl Fieri. I’ll go anywhere that Guy has been. DJ’s on Duval is top notch fried seafood in a paper basket. Guy had the garlic butter clams but it’s also a great place to try some conch fritters in the Conch Republic.

Key West Cemetery
In typical Madeline fashion, I have to add some dark tourism. However, many consider this a delightful place to visit as it’s known for it’s wacky epitaphs. There’s even a brochure at the front gate for a self-guided tour of some oddly unique headstones. (WATCH my tour of the Key West Cemetery).

Key West is one of the coolest towns in the United States. Enjoy your time here, hop a bicycle, see some six-toed cats, and eat as much Key Lime Pie as you can!