Mini South Florida Gateway: From Key West to the Everglades and The Gulf Coast

Mini South Florida Gateway: The Starting Itinerary

This itinerary can be arranged as a standalone gateway or integrated into a longer extension to your Miami vacation!

Day 1: Arrival in Miami → Upper Florida Keys (Key Largo / Islamorada area)

Today is designed to be flexible depending on your arrival plans.

• Arriving in Miami today: pick up your rental SUV at the airport and begin driving south toward the Florida Keys. Depending on how you’re feeling, you can either aim for the gateway area near Homestead first or continue directly to the Upper Keys.
• Already in Miami: pick up your vehicle in the morning and head straight to the Keys for a more relaxed start.

The Upper Keys are ideal for easing into “island time.” If you’d like, we can layer in optional experiences such as snorkeling, diving, or a sunset cruise, followed by a waterfront dinner.

Driving guide (approx.):

• Miami Airport → Homestead: ~35 miles / 56 km
• Miami Airport → Key Largo: ~64 miles / 103 km

Night: Upper Florida Keys (Key Largo / Islamorada area), 4-star superior waterfront hotel or resort (preferred network). Upgrades can include a more exclusive boutique or luxury-style waterfront stay where available.

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Day 2: Upper Keys / Homestead → Key West

Drive south to Key West via the legendary Overseas Highway—one of America’s most memorable scenic routes, linking island to island across dozens of bridges and turquoise water views. We recommend taking your time today with relaxed stops, short viewpoints, and a comfortable pace.

Arrive in Key West by early afternoon, check in, and enjoy the island largely on foot. Key West is best experienced through its atmosphere: historic streets, galleries and shops, classic landmarks (such as Hemingway-era heritage sites), and a relaxed evening scene with live music and Caribbean-influenced flavors.

Driving guide (approx.): ~2 hr 45 min / 128 miles (206 km), plus scenic stops

Night: Key West, 4-star superior boutique hotel or resort (preferred network), with an optional upgrade to 5-star luxury.

Optional extension (highly recommended if time allows): add one extra night in Key West for a full day of activities such as a Dry Tortugas day trip, private boating, jet skis, snorkeling, or a sunset sail.

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Day 3: Key West → Everglades area (Alligator Alley) → Marco Island (Gulf Coast)

Enjoy a relaxed morning in Key West—either to finish sightseeing or simply to slow down and enjoy the island rhythm. Then begin the drive back north before turning west across Florida via the Alligator Alley corridor.

This afternoon is dedicated to the Everglades chapter of the trip. Depending on your preferred style, we can recommend an experience that ranges from adventure-forward (airboat-style) to more comfort-forward (guided eco touring), all focused on Florida’s unique wildlife and ecosystems.

Continue on to the Marco Island area for a calm, resort-style evening on the Gulf Coast.

Night: Marco Island area, 4-star superior beachfront resort (preferred network).
Luxury upgrades can be added here, especially for beachfront room categories and resort amenities.

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Day 4: Marco Island → Naples → Miami (End of service)

Wake up on Florida’s Gulf Coast and enjoy a slower morning—this side of the state often feels calmer and more “resort-like” than the Atlantic coast. We recommend spending a few hours in Naples for a beach walk and a polished coastal-town atmosphere before beginning the drive back to Miami.

Arrive in Miami by late afternoon, return the vehicle, and conclude services.

Driving guide (approx.): Naples → Miami ~2 hrs (traffic dependent)

End of service.
Optional extension: add a 3-night Miami stay either before or after the itinerary (upscale family-friendly or couples’ lifestyle-luxury style).

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Route overview: Mini South Florida Gateway at a glance

Let’s design your Mini South Florida Gateway

In just a few days, this itinerary delivers the signature South Florida contrasts—island scenery in the Florida Keys, the wild beauty of the Everglades, and a final exhale on the Gulf Coast with an overnight in the Marco Island area. It’s the perfect add-on to a Miami stay (or a stand-alone escape) when you want more than the city—without committing to a full-length road trip.

We don’t plan this as a “one-size-fits-all” loop. We tailor the pacing, routing, and hotel style to match your travel personality—whether you’re looking for an upscale, easy-going getaway with smooth logistics, or a more boutique, lifestyle-forward escape with upgraded stays and curated add-ons like snorkeling/boat time in the Keys, or a guided Everglades experience.

Ready to start planning? Share your preferred dates, where you’re starting from (Miami arrival or already in town), and your ideal travel style—and we’ll craft a personalized Mini South Florida Gateway built around your priorities.