Key West to Miami Beach: The Ultimate South Florida Road Trip Itinerary
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I've done my fair share of road trips, but my absolute favorite is the drive from Key West to Miami Beach on south Florida's Overseas Highway (aka U.S. Route 1). The drive is long (170 miles at a slow-going 45 mph to be exact) but the ocean views, hidden beaches, and endless tiki bars along the way make the experience a genuine blast. I recently did the drive and spread it out over 6 days/5 nights, staying at three stunning properties—The Marker Key West, Cheeca Lodge, and the St. Regis Bal Harbour—along the way. Here's my exact itinerary—including what I ate and drank and where I hung out—for you to screenshot, so when you finally book your flight to Key West and nail down that car rental, all you'll have to do is show up and hit the road.
(FYI, The writer received comped accommodations, meals, and experiences during this getaway.)
Nights 1 and 2: Key West
Stay:
The Market Key West: The Marker is exactly what you'd expect Key West to be: beachy, laid-back, and an all-around great time. The location is the absolute best—it's right on the harbor and a three minute walk from the top of Duval Street where all the bars, restaurants, and live music spots are. The rooms are bright and airy (ask for one with a water view for optimal sunset viewing) and the secluded pool is the perfect spot for a dip and frozen cocktail at the end of the day.
Book yourself a room at The Marker right now: Shop Now
Play:
Bar hop on Duval Street: Key West has a super fun party scene and there is no shortage of dive bars and beach bars to check out while you're in town. There's live music pretty much everywhere and the vibe is always casual, so showing up in your bathing suit and coverup whether it's 12pm or midnight is not only acceptable, it's encouraged. Some can't-skip spots include: Hog's Breath, Sloppy Joe's, Bull & Whistle, Irish Kevin's, and The Rum Bar.
Rent a scooter and explore: Key West is small enough that you don't need a car to get around but it's also too big too cover on foot, which is why you absolutely need to explore the island via scooter. Walk out the front door of The Marker toward the harbor and you'll find at least 10 different kiosks renting scooters for the day. Explore the different neighborhoods and check out Smather's Beach and Simonton beach for swimming, Fort Zachary Taylor State Park for snorkeling, the Southernmost House for drinks and snacks, the Casa Marina Hotel for more drinks and snacks, and Mallory Square for sunset.
Eat:
Louie’s Backyard: Sure, Duval Street is fun, but the majority of the restaurants can be a bit cheesy or over-priced. My suggestion? Head a few blocks off the beaten path to Louie's Backyard. The view, the food, the drinks...it's all exceptionally good at this low-key locals spot. We sat outside on the back deck for rosé and Sunday brunch, but the dinner menu is 10/10 too.
Cuban Coffee Queen: I'm not going to lie to you, I woke up both mornings in Key West mildly hungover and the cafe con leche and rice and beans from this place brought me back to life. It's super casual (you just order at the window and find the nearest bench to devour your food) and you'll likely have to wait in line, but it's so worth it.
Night 3: Islamorada
Stay:
Cheeca Lodge and Spa: Get in the car and drive about an hour and 40 minutes east on the overseas highway to the Cheeca Lodge. The storied resort is located in Islamorada, a stretch of islands in the middle of the keys known for fishing, water sports, and locally sourced seafood. We spent the night in one of the new casitas and it was nothing short of spectacular. Not only are the casitas spacious and meticulously decorated and designed, they're situated on a private beach that's absolutely stunning and stocked with fun water toys like kayaks and stand up paddle boards.
Book yourself a room at Cheeca Lodge right now: Shop Now
Eat:
Atlantic's Edge: If you're a seafood fan, then you'll love Atlantic's Edge (the main dining spot at Cheeca Lodge). Time your res with sunset and ask for an outside table, then order the clams and bacon and snapper piccata and enjoy some of the freshest, most delicious fish you've ever had.
Play:
Beach time: Grab nothing but your book and your sunscreen, head to the bar for a glass of wine, and then plop yourself on one of the plush, oversized beach chairs facing the water to do...absolutely nothing. If your day consists of anything more than lounging, snoozing, and taking the occasional ocean dip, you're doing it all wrong.
Nights 4 and 5: Miami Beach
Stay:
St. Regis Bal Harbour: Hop back in the car and drive two hours northeast to Bal Harbour (a swanky neighbor in north Miami Beach) and check in at the St. Regis for a two-night stay. If you've been to a St. Regis before then you know the vibe, if not, you're in for a real treat. The property is the ultimate spot for a luxury R&R experience. Everything from the way you're greeted at morning coffee to the way the person at the pool sets up your chair and towel just feels fancy and elevated. And the fact that the resort is situated on one of the cleanest, prettiest stretches of Miami Beach doesn't hurt either.
Book yourself a room at the St. Regis Bal Harbour right now: Shop Now
Eat:
St. Regis Bar: Sushi and cocktails are the move here. My husband and I ordered all the rolls (literally) and spicy margaritas, which, no joke, were the best spicy margs we've ever had. They're like dangerously good, so proceed with caution.
Jaya: If you want to venture off the property for dinner, Jaya at the Setai Hotel, Miami Beach is a great spot. It feels more like a night out than dinner thanks to the lounge-y decor and fire breathing dancers but don't worry—the food is delicious. Don't miss the truffle dumplings and sea bass tikka. And obvs drink your dessert with an espresso martini (or two).
Play:
Spa time: Forget the basic massage (you can get that anywhere, okay?) and book yourself the 24K gold wrap—it's one of the signature treatment's at the St. Regis Spa and I've never experienced anything like it (which says a lot considering I'm a seasoned beauty editor). The treatment involves full-body exfoliation, a detoxifying clay mask, and a relaxing deep-tissue massage that'll leave your skin ridiculously smooth and soft and your muscles feeling totally relaxed. Be sure to block out some time to enjoy all the spa amenities post-treatment, including the steam room and plunge pool.
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