Leo’s Favorite 2-Day Fun Road Trip to Key West

miamiconvertibles
Jun 3
3 min read

This one’s personal—your must-do, must-try Keys escape curated by the Chief Mustang Driver himself. Cruise from Miami Beach in a top-of-the-line Mustang convertible, dive into crystal-clear snorkeling, zip around on a jet ski, and savor fresh seafood paired with cold craft beers. Explore Key West by bike or hop on the famous Conch Train for a laid-back island tour. With boutique hotels, sunset cocktails, and seamless valet service, this is the ultimate two-day getaway for those who love the thrill of the road and the chill of island life.

Day 1: Miami Beach → Key West – Adventure & Island Flavor

🕖 7:00 AM – Pick Up Your Mustang Convertible at Miami Convertibles Miami Beach

Start early and grab your ride. Roof down, music up, and the open road calling.

🍍 8:00 AM – Light Breakfast at Robert Is Here Fruit Stand

Fuel up with fresh tropical fruit smoothies and grab a guava or mango pastry to keep your energy high.

🐠 10:00 AM – Snorkeling at John Pennekamp Coral Reef State Park (Key Largo)

Dive into the crystal-clear waters on a guided snorkeling trip to see vibrant coral reefs and marine life. Leo’s favorite—bring your underwater camera!

🛥️ 12:30 PM – Jet Ski Rental in Islamorada

Feel the adrenaline with a jet ski ride over Florida Bay’s sparkling waters—speed, sunshine, and pure fun.

🦞 2:00 PM – Lunch at Lazy Days Restaurant

Enjoy fresh seafood with water views. Conch fritters, mahi-mahi sandwiches, and a cold local beer to refuel.

🚴‍♂️ 3:30 PM – Scenic Bike Ride in Marathon

Stretch your legs with a relaxing bike ride along the Florida Keys Overseas Heritage Trail—ocean breeze included.

🌉 5:00 PM – Drive the Iconic Seven Mile Bridge

This is convertible cruising at its finest—ocean on both sides, the sun setting, and the wind in your hair.

🏨 6:30 PM – Check-in at a Boutique Hotel in Key West

Leo’s picks:

The Gardens Hotel for tropical charm
Ocean Key Resort & Spa for harbor views and luxury

🌅 7:30 PM – Sunset Cruise or Cocktails at Sunset Pier

Sip a cold one while watching Key West’s famous sunset. If you want to keep moving, hop on the Conch Train for a relaxed island tour after.

🍽️ 8:30 PM – Dinner at Blue Heaven

Island vibes and legendary food—go for the lobster Benedict or Caribbean jerk chicken, paired with a cold craft beer.

Day 2: Key West Exploration + Return to Miami

🌞 9:00 AM – Breakfast or Brunch at Sarabeth’s

A hearty start with gourmet pastries, eggs Benedict, and fresh coffee.

🚲 10:30 AM – Bike the Old Town Loop

Explore the colorful streets, pop into Ernest Hemingway’s House, or just cruise Duval Street on two wheels.

🎟️ 12:00 PM – Hop on the Key West Conch Train Tour

Learn the island’s history with fun stories and laid-back sightseeing—a must-do for first-timers.

🍤 1:00 PM – Lunch at Garbo’s Grill

Casual but iconic—tacos, fresh fish, and killer street food vibes.

🛣️ 2:30 PM – Head Back to Miami via Overseas Highway

Take it easy on the drive back with optional stops:

Beach walk at Bahia Honda State Park
Coffee break at Keys Coffee Co. in Marathon

🌌 7:30 PM – Return Your Mustang Convertible at Miami Convertibles or Valet at Your Hotel

Valet the car directly at your Miami Beach hotel or return to our garage. Please coordinate with a Miami Convertibles representative for next-day pickup from valet.

Ready to hit the road? Book your Mustang or Jeep now and start your Key West adventure!