The best of Miami to Key West

If you love manatees, fish taxidermy and sunsets that make your heart sparkle, it’s time for an epic road trip from Miami to Key West.

QUESTION: how many photos can one person take of a sunset? Answer: INFINITY.

We flew into Miami and flew out of Key West. This was a game-changer since Miami’s airport is insane-o and Key West’s is a walk-in closet. It’s easy and breezy and great AND you don’t have to backtrack.

We only stayed a day in Miami, but booked a “Manatee Photo Safari” tour in Virginia Keys. Manatees are the “Buddhas of the Sea” and it was soooooo magical seeing them up close and personal. We also saw the Miami skyline and the “chicken of the tree”—aka: fat iguanas sunbathing in branches along the mangroves.

 First stop: “Robert is here” https://www.robertishere.com/

This place was 100% worth its out-of-the-wayness: 19200 SW 344th Street in Homestead, FL. Stop for the key lime milkshake and snacks, stay for the mini zoo out back! There are parakeets n’ goats n’ turtles n’ ducks n’ baby calves. (SQUEEEEAL!) Robert started out with a card table, a sign and a few cucumbers for sale some 50 years ago, and now this sweet li’l roadside stand has become a full-blown tourist attraction. Big, big fan!

Second stop? Alabama Jacks! https://www.floridabeachbar.com/alabama-jacks

We stopped at A LOT of dive bars on the way to Key West and this was our fave. Try to get a spot at the bar and order up a cold one. Great vibe, right on the water: 58000 Card Sound Road, Key Largo.

We stayed the night at Postcard Inn in Islamorada: https://www.holidayisle.com/

This hotel was adorable (hello, swim-up bar, water trampoline, cornhole, ping pong, standup paddleboards, bocce ball)! Soooooo many fun activities and stellar craft beer selection. We watched the sunset at the Raw Bar and had two orders of the smoked fish spread. Deeee-lish.

Third stop? Robbie’s to feed the the giganto tarpon! https://www.robbies.com/

Let the record show, this place is insane. There are some fun antique shops, cold drinks and little pop-up markets too, but feeding these 8-foot, 200-pound tarpons is something else. Not necessarily because the fish are scary, but because THE PELICANS ARE.

They are out in droves and everywhere you turn you’ll feel like you’re in a Hitchcock film. BUT we saw two manatees smooch under the pier so it was probably the single best stop we made on our road trip. (SQUEEEEEAL)

Fourth stop? Key Fisheries for a Lobster Reuben: https://www.keysfisheries.com/

This sandwich was exponentially more delicious than I ever could have imagined. Order it up and head to the “tree house” overlooking the water. It’s a sweet, airy spot where you can order some boozy treats.

Our next overnight was in Marathon at THE most gorgeous resort that we wish we never had to leave: Isla Bella! https://www.islabellabeachresort.com/

Rooms with a lanai? GORGEOUS. Fire pits and outdoor seating/restaurants for optimal sunset views? SUBLIME. Beach chairs + breezy hammocks? NO WORDS. Adorable marketplace that took all my money? DEFINITELY. Pool with dreamy cabanas? YES YES YES.

This place was perfect. There are cute little activities for kiddos and adults (WE MISSED BINGO) but made it for the fireworks <—(gasp) and the sun setting, as we sipped on our complimentary champagne. Get your flowy beach robes ready and book this place immediately.

Fifth stop? Baby’s Coffee: https://babyscoffee.com/

We accidentally blew past this place, but the outside was SO FREAKING ADORABLE that I did lots o’ research and concluded it is well worth a stop. Coffee, sammies and key lime pie. YES, PLEASE.

Observation: if you’re not in a Mustang convertible, are you even in Key West?!! Key West is definitely an interesting place. It feels a liiiiiiittle like a geriatric spring break, but there are still loads o’ fun things to see and do. I think a sunset cruise would be too-too, but here are our fave mainland activities in the Conch Republic.

Ernest Hemingway’s home-turned-museum was genuinely amazing. Loved seeing all the memorabilia and decor AND the six-toed cats that live on the property (and still sleep in his bed). There’s a Picasso cat statue he traded for a case of hand grenades. You can “meet” his four wives. You can see the writing studio where he wrote 70% of his life’s work. This is a true gem.

Blue Heaven is an al fresco restaurant with a yard full o’ chickens. Come for the key lime pie, stay for the live music! https://blueheavenkw.com/ There are some cute shops nearby that you can also pop into. “Bésame Mucho” is supes cute: https://besamemucho.net/

Our fave restaurant in Key West was actually Garbo’s Grill, a tiny airstream trailer with super fresh fare—it’s behind a bar called Hank’s. The Yum Yum shrimp and Korean BBQ tacos are bomb: http://www.garbosgrillkw.com/

Favorite bar goes to Captain Tony’s Saloon! It’s been around since 1933 and has pool tables and live music. Famous patrons include, but are not limited to: Jimmy Buffet, JFK, Shel Silverstein and of course, Hemingway himself. There’s a fun tradition of trying to toss a coin into the Goliath Grouper’s mouth out front. Technique is: turn your back to the fish and throw the coin over your shoulder. If you make it, you’re rewarded with good luck for a year. WOOT WOOT!

Then it’s time for another one last epic sunset at Mallory Square. Find yourself a cabana close to Havana (this is the southernmost point of the USofA after all), and wash it all down with your 87th slice of key lime pie. Miami to Key West road trip is officially a wrap!