Sun, Sand & Hemingway: 9 Must-See Stops from Miami to Key West
- Jul 18, 2025
- 5 min read
When December rolls around in Florida, temperatures hover between 60°F and 86°F—making Miami Beach and South Beach prime spots for holiday escapes. For many, the lovely energy and year-round warmth are exactly what winter needs.
Head 100 miles south, and you’ll discover 1,700 keys—tiny islands stretching clear into the Florida Straits, begging for exploration during the northern hemisphere’s coldest months.
Image by miami2you / Adobestock
1. The famous Overseas Highway
Let’s begin with one of the most famous road trips in the U.S.: the Overseas Highway. This extension of US Route 1, built in 1938 atop an old railway, spans over 150 miles of stunning bridges and island vistas.
As you drive, the Atlantic shines to your east and the Gulf of Mexico to your west—proof that sometimes the journey is the ultimate destination.
2. Miami
No South Florida itinerary begins without Miami. It’s more than just Ocean Drive and luxury resorts—it’s a hub of culture, design, and cuisine.
Stroll through Wynwood’s cool murals, explore cutting-edge exhibits at Pérez Art Museum, or shop the upscale boutiques of the Design District. And don’t miss Little Havana, where Cuban coffee and cobbled streets offer a soulful counterpoint to the city’s tropical glamour.
3. Miami food tour
Before you hit the road to the Keys, embark on a Miami food tour. It’s the best way to experience the melting-pot flavors of the city—fresh-caught ceviches, Cuban-style pork, arepas, and more—all while supporting local chefs and walking off brunch along Miami’s colorful neighborhoods.
It’s a culinary kickoff that ties the city’s cultural threads together in one delicious outing.
Image by Sara Free / Pexels
4. Mangroves at John Pennekamp
Your first taste of the Keys arrives with a side of nature. En route to Key Largo, stop at John Pennekamp Coral Reef State Park—America’s first undersea park.
Stroll scenic mangrove trails, kayak through winding waters, or snorkel above coral reefs teeming with marine life. It’s a vital ecosystem that protects coastal Florida and offers peaceful reflection only miles from busy Miami.
5. Seven Mile Bridge
Crossing the Seven Mile Bridge is a must. Built in 1912—then dubbed one of the world’s longest bridges—it’s a feat of engineering that connects the Middle Keys to the Lower Keys. With the ocean stretching infinitely on either side, every mile feels like a postcard comes to life.
6. Founders Park, Islamorada
Further southwest, Founders Park is a great place for a beach escape with the whole family. Less crowded and more natural than Miami’s shores, it’s perfect for swimming, picnicking, and kayaking among lush botanical gardens.
Nearby Bayfront restaurants serve eco-conscious bites, ideal after a morning of splash-and-play by the water.
Image by Gian / Adobestock
7. The Fish House
The Fish House Restaurant and Seefood Market, located in Islamorada, is a place with 25 years of seafood excellence. Enjoy fresh grouper, Mahi-Mahi, lobster, and the salted Key Lime Pie, all in a laid-back setting reminiscent of Hemingway’s era. With a 4.4 TripAdvisor rating, it’s a Keys classic rooted in community and flavor.
Lazy Lobster Seafood Restaurant is another must-visit for seafood lovers! The lobster rolls, seafood platters, and—most importantly—the free banana bread are highly praised by visitors. The relaxed atmosphere, friendly service, and huge plates are remarkable.
8. Key West
As you cruise into Key West—the very end of the highway—you’re walking into living literary history. Ernest Hemingway lived and wrote here for nearly a decade, and the town retains his spirit: easygoing, creative, and a little wild.
Duval Street has Cuban-influenced bites and live music in every bar. Tour Hemingway’s house, where his six-toed cats still rove. The $19 entry ($7 for children ages 6-12) gains you access to his writing room and lush, tranquil gardens.
9. Dry Tortugas National Park
Just beyond Key West lies a remote jewel: Dry Tortugas, a group of tiny islands reachable only by ferry or seaplane. The most popular way to reach the Dry Tortugas is by ferry: the Yankee Freedom III. A 2.5-hour ferry ride, that becomes a magical journey through turquoise waters, leaving you on the island for only four to five hours if you're on a day trip.
Known for Fort Jefferson and pristine snorkeling spots, this is one of America’s most isolated national parks. Pack your tent and camping gear—or visit by day—to soak in history, untouched beaches, and underwater wonders teeming with color.
Admission to Dry Tortugas National Park is $15 per person and is valid for 7 consecutive days. Children under 15 years of age are exempt from admission (including international visitors).
Image by miami2you / Adobestock
Why is food so remarkable in Florida?
You might wonder why I mention Miami food tour twice. Here's the simple truth: South Florida’s tastescape changes every season, and a guided food journey is perfect before and after your Keys road trip.
Start in Miami, then end your route in Key West with a second Miami food tour–style culinary spree at famous fish houses, roadside conch stands, and retro diners. Each dish has flavors shaped by Caribbean waves, Latin American traditions, and coastal creativity—an experience best savored slowly.
Travel tips & wellness highlights
Preparation: The Overseas Highway is gorgeous but remote — bring snacks, water, and backup phone chargers.
Wellness Stops: Pack hiking shoes for mangrove paths, snorkeling gear for coral encounters, and breathable layers for sun-soaked days.
Family-Friendly: From beach days in Islamorada to camping at Dry Tortugas, this trip balances activity and relaxation.
Local Flavors: Try island-grown citrus in cocktails, locally caught stone crabs, and of course Key Lime Pie—better when shared at sunset.
Immerse in History: Visit Hemingway’s home, or Truman’s Little White House, where Harry S. Truman spent 175 days as president, learning about his unique role. For those interested in American politics and history, a visit to both museums is mandatory.
Final thoughts
Miami to Key West isn’t just a drive: it’s a journey through warmth, heritage, and connection. Winter grey skies fade behind you as you slice through turquoise waters. Every stop—whether on land, sea, or at sunset-splashed cafes—brings you closer to Florida’s soul: sun-drenched beaches, tropical ecosystems, and tales of writers, fishermen, and explorers. Bring your sunscreen, your open mind, and your appetite.
Because after two Miami food tour experiences and nine unforgettable stops, you’ll have fallen in love—with the sea breeze, the keys, and maybe even a little bit of Hemingway’s spirit. So when you're planning your next escape—or drafting that online magazine story—remember: the real magic of Florida starts here.