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Follow Us from Miami to Key West Road Trip

Stretching a grand total of 500 miles from top to bottom, road tripping the entire state of Florida can by tough! Theme parks, water parks, resorts—all of these can get a little … bland? So why not head straight for Miami, a tropical hotspot full of music and food and art. Once you've partied on South Beach, why not keep heading south to Key West! The total drive is just 4 hours, but will feel like a completely new world. can change your entire surroundings, and bring up some unexpected adventures. Let's hit the road! 

The Itinerary

Leg 1: Miami–Islamorada
Head south toward Florida's famous Highway 1. Stop off about halfway through to feed the wildlife at Robbie's Restaurant. (91 miles; about 2 hours 15 minutes)
Leg 2: Islamorada–Marathon Key
Make a pit stop for a chance to see loggerhead turtles and dolphins. (30 miles; about 40 minutes)
Leg 3: Marathon Key–Key West
Last call! Stop in to the southernmost point of the contiguous U.S.!
Total time: 3 hours 30 minutes
Total miles: 167 miles


Starting Point: Stubborn Seed in Miami

Start your trip with a great meal and cocktail at local hot spot Stubborn Seed. (101 Washington Ave, Miami Beach, FL) Here, Top Chef alum Jeremy Ford serves up American-style cuisine, alongside a brilliant and eclectic cocktail menu. Most notably, the Silver Dollar Old Fashioned steals the show. This DIY cocktail comes with all the ingredients on a silver platter. From there, guests concoct their own drink with their preferred ratios. Don't forget to cheers to the trip!
Robbie's Restaurant in Islamorada
Hop on the Coastal Overseas Highway US RT1, and get some miles under your belt! Your next destination may sound fishy, but that is quite literally the point. After passing by Key Largo, your next destination is Islamorada, and the world-famous Robbie's Restaurant, where guests dine and relax with ocean views and also feed giant wild tarpon! (77522 Overseas Hwy, Islamorada, FL 33036) These game fish can grow to 8 feet long, and weigh as much as 200 pounds. At Robbie's, guests are welcomed to feed this monsters BY HAND! No joke! Bait and tackle are available for traditional fishing as well.

See the Sun set on the Water in Marathon Key

This road trip can be done in just under four hours, but why not slow down and enjoy the ride? Stop off in Marathon Key for a beautiful beachside sunset and a chance to walk the famous Seven Mile Bridge—one of the longest bridges in the world! Built in 1912 as a train route, the original road runs alongside the highway, but has been converted into a walking and bike path with incredible views. After soaking in the sun, a stop at Keys Fisheries is in order. (3502 Gulfview Ave, Marathon, FL 33050) This open-air fish house overlooks the bay and is quite famous for the conch fritters, a local favorite.

The Final Leg: Key West & The Southernmost Point

When you've gone as far as you can go, you will know you have arrived. You've run out of road to trip at the Southernmost Point Buoy. (Whitehead St & South Street, Key West, FL 33040) Here, you will find yourself standing at the edge of the entire country! Perfect for posterity or Instagram, capture the heart of this trip with a classic group photo to remember your time.
Now its time to stretch your legs, and enjoy the sun. Wander the grounds of Ernest Hemingway's estate and see how many of the 50+ 6-toed cats you can spot. Since the writer's time there in the 1920s, these furry little ones have taken over in the most adorable hostile land siege ever! Rent a bike or scooter to explore the laid-back bars, restaurants, and shops along Duval Street.