The Ultimate 5-Day Florida Keys Road Trip Itinerary: Where to Stay, Eat & Explore
Written By: Jamie Cassidy | Road & Table Travel
Table of Contents:
More than just Key West
The Florida Keys seem to be one of those destinations people either love or leave wondering what all the hype is about. As a travel advisor, I hear both sides all the time.
Personally, I don't think it's the destination that's the problem—I think it's how you experience it.
Stretching more than 100 miles from Key Largo to Key West, the Florida Keys are home to one of America's most iconic road trips. The Overseas Highway connects a chain of tropical islands where turquoise waters, beautiful state parks, fresh seafood, and quirky roadside stops make the journey just as memorable as the destination.
At Road & Table, I believe the best way to experience the Keys is by slowing down, savoring the local flavors, and exploring beyond the obvious. This 5-day itinerary will help you discover the best places to stay, eat, snorkel, and explore from Key Largo to Key West—so you can experience the Florida Keys the Road & Table way.
Which Airport Should You Fly Into?
- Miami International Airport (MIA): The best overall option with the most flight choices and about a 1-hour drive to Key Largo.
- Fort Lauderdale-Hollywood International Airport (FLL): Often offers lower airfares and is about 1½ hours from Key Largo.
- Key West International Airport (EYW): A great option if you're only visiting Key West, but less practical if you're planning to explore the entire island chain.
Road & Table Tip: Consider flying into Miami or Fort Lauderdale and flying home from Key West. While an open-jaw itinerary typically costs a bit more, it saves you from making the 4+ hour drive back to the mainland. Traffic on the Overseas Highway can become quite heavy, especially on weekends and during peak travel seasons, making this a worthwhile upgrade if it fits your budget.
Do You Need a Rental Car?
Yes. A rental car is the best way to experience the Florida Keys. The Overseas Highway is one of America's most scenic drives, and having your own vehicle allows you to stop at hidden beaches, waterfront restaurants, scenic overlooks, and local attractions along the way.
Florida Keys Overview
The Florida Keys aren't one destination—they're a chain of islands, each with its own personality. Here's what makes each one worth visiting.
📍 Key Largo
Known for: World-class snorkeling, diving, and easy access to the Keys.
- Best For: Snorkeling, diving, waterfront dining, and nature lovers.
- Don't Miss: John Pennekamp Coral Reef State Park.
- Recommended Stay: 1 night.
📍 Islamorada
Known for: Sport fishing, laid-back island charm, and incredible seafood.
- Best For: Fresh seafood, breweries, beaches, and local culture.
- Don't Miss: Robbie's Marina and Anne's Beach.
- Recommended Stay: Half to 1 day.
📍 Marathon
Known for: Beautiful beaches, boating, and family-friendly adventures.
- Best For: State parks, snorkeling, wildlife, and relaxing beach days.
- Don't Miss: Bahia Honda State Park and the Turtle Hospital.
- Recommended Stay: 2 nights. ⭐
📍 Big Pine Key
Known for: Quiet natural beauty and unique wildlife.
- Best For: Scenic drives, hiking, kayaking, and escaping the crowds.
- Don't Miss: National Key Deer Refuge and Blue Hole.
- Recommended Stay: Visit as a stop between Marathon and Key West.
📍 Key West
Known for: Historic streets, vibrant nightlife, and iconic sunsets.
- Best For: History, restaurants, shopping, and sunset celebrations.
- Don't Miss: Duval Street, Mallory Square, and the Southernmost Point.
- Recommended Stay: 2 nights.
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Where to Stay in the Florida Keys
Choosing the right hotel can completely transform your Florida Keys experience. Rather than staying in one place, I recommend splitting your stay between Marathon and Key West. This allows you to experience the unique personality of each island while cutting down on driving and making the most of your time.
Key Largo
Playa Largo Resort & Spa ⭐ Road & Table Pick
A luxurious beachfront resort with spacious rooms, multiple restaurants, a private beach, and plenty of opportunities to get out on the water. It's an ideal choice if you're looking for a full-service resort at the gateway to the Keys.
Perfect for: Luxury travelers, families, and couples
A tranquil bayfront retreat with tropical gardens, a private beach, complimentary paddleboards, and spectacular sunset views. It's a favorite for travelers seeking a quieter side of the Florida Keys.
Perfect for: Romantic getaways and peaceful escapes
Islamorada
One of the Florida Keys' most iconic luxury resorts, Cheeca Lodge combines elegant accommodations with a private beach, world-class fishing, multiple restaurants, and a relaxing spa.
Perfect for: Couples, anniversaries, and luxury vacations
Marathon
Isla Bella Beach Resort ⭐ Road & Table Favorite
If I could recommend just one resort for a Florida Keys road trip, this would be it. Oceanfront rooms, multiple pools, exceptional dining, and a central location make it the perfect home base for exploring the Middle Keys.
Perfect for: Couples, families, and first-time visitors
Key West
Oceans Edge Resort & Marina ⭐ Road & Table Luxury Pick
One of my favorite luxury resorts in the Keys, Oceans Edge offers oversized guest rooms, six pools, marina views, and a quieter atmosphere on Stock Island while providing complimentary shuttle service into Old Town.
Perfect for: Luxury travelers, couples, and boaters
A sophisticated waterfront boutique resort known for spacious rooms, exceptional dining, and a relaxed marina setting away from the crowds.
Perfect for: Couples and food lovers
A charming boutique hotel tucked away in the heart of Old Town. Surrounded by lush tropical gardens, it's one of the most romantic and peaceful places to stay in Key West.
Perfect for: Couples seeking a boutique experience
Road & Table Recommendation
For this itinerary, I recommend spending
three nights in Marathon followed by
two nights in Key West. Marathon places you within easy reach of Key Largo, Islamorada, Bahia Honda State Park, and the Middle Keys, while finishing your trip in Key West lets you enjoy its incredible restaurants, historic charm, and famous sunsets before flying home.
Best Beaches in the Florida Keys
Unlike many Florida beach destinations, the Florida Keys aren't known for miles of wide, sandy shoreline. Instead, you'll find smaller beaches, crystal-clear water, scenic state parks, and quiet places to relax. If you're looking for the best beaches in the Keys, these are the ones I recommend.
Bahia Honda State Park ⭐ Road & Table Favorite
If there's one beach you shouldn't miss, it's Bahia Honda State Park. With turquoise water, soft sand, and beautiful scenery, it's widely considered one of the best beaches in the Florida Keys.
Why You'll Love It
- Crystal-clear turquoise water
- Soft sandy beach
- Excellent swimming
- Nature trails
- Picnic areas
- Showers, restrooms, and concessions
Road & Table Tip
Head to
Sandspur Beach for the best experience. Arrive early—especially on weekends—as the park often reaches capacity before midday.
Located in Islamorada, Anne's Beach is more about the peaceful setting than a traditional beach day. It's the perfect place to stretch your legs, enjoy the views, or stop for a picnic while driving the Overseas Highway.
Why You'll Love It
- Scenic boardwalk
- Shallow, calm water
- Picnic pavilions
- Great stop along the Overseas Highway
Know Before You Go
The amount of exposed beach depends on the tide, and seasonal seaweed is common. Low tide typically offers the best experience.
One of Marathon's best public beaches, Sombrero Beach is ideal for families looking for soft sand and calm water.
Why You'll Love It
- Soft sandy beach
- Calm swimming conditions
- Picnic shelters
- Volleyball courts
- Free parking
Good to Know
Sea turtles nest here seasonally, so be sure to respect protected nesting areas if visiting between April and October.
Fort Zachary Taylor Historic State Park
This Key West favorite combines history with one of the clearest snorkeling beaches on the island.
Why You'll Love It
- Excellent snorkeling
- Clear water
- Historic Civil War fort
- Shaded picnic areas
- Beautiful sunsets
Road & Table Tip
Bring water shoes—the shoreline is naturally rocky, making them well worth packing.
Best Snorkeling in the Florida Keys
The Florida Keys are home to the only living coral barrier reef in the continental United States, making them one of the country's best snorkeling destinations. Whether it's your first time or your fiftieth, exploring the reefs is an experience you won't want to miss.
Sombrero Reef ⭐ Road & Table Favorite
If I could recommend just one snorkeling experience in the Florida Keys, it would be Sombrero Reef.
The crystal-clear water, colorful coral, and abundance of tropical fish made this one of the highlights of my entire trip. From the moment I slipped into the water, I was completely hooked.
Why You'll Love It
- Crystal-clear turquoise water
- Vibrant coral reef
- Colorful tropical fish
- Excellent visibility
- Great for all experience levels
Good to Know
- Located just offshore from Marathon
- Accessible by guided snorkeling tours
- Conditions are typically best in the morning
I can't say enough good things about Spirit Snorkeling. If you're looking for a tour company, this is the one I recommend.
The crew was friendly, knowledgeable, and made everyone feel comfortable before we even entered the water. Whether you're snorkeling for the first time or have years of experience, they do an excellent job creating a fun and relaxed experience.
Why I Recommend Them
- Friendly, knowledgeable crew
- Excellent for first-time snorkelers
- Family-friendly atmosphere
- Well-organized excursions
- Direct access to Sombrero Reef
Road & Table Tip
Book a morning tour whenever possible. You'll usually enjoy calmer seas, better visibility, and a more enjoyable snorkeling experience.
What to Bring
Don't forget to pack:
- Reef-safe sunscreen
- Towel
- Sunglasses & hat
- Waterproof phone case or underwater camera
- Motion sickness medication (if needed)
Best Restaurants and Where to Eat
One of the best parts of a Florida Keys road trip is the food. From fresh-off-the-boat seafood to waterfront restaurants where you'll want to linger long after your meal, every island offers something worth stopping for.
While there are plenty of tourist hotspots, these are the restaurants I'd recommend to friends—and the ones I'd happily return to myself.
Quick Picks
⭐ Best Overall: Porky's Bayside Restaurant & Marina
🦞 Best Seafood: Keys Fisheries
🌅 Best Waterfront Dining: Lazy Days
🥂 Best Special Occasion: Chef Michael's
🥞 Best Breakfast: Blue Heaven
🥧 Best Key Lime Pie: Blue Heaven
🍔 Best Casual Lunch: Hobo's Café
📍 Key Largo
Hobo's Café ⭐ Road & Table Favorite
One of my favorite casual stops in the Florida Keys, Hobo's Café is exactly the kind of place I love discovering while traveling. It's relaxed, welcoming, and consistently serves great food without feeling touristy.
Best For
- Casual lunch
- Fresh seafood
- Burgers and sandwiches
Don't Miss
- Fish sandwich
- Fresh catch specials
- Homemade Key lime pie
A true Florida Keys institution, Mrs. Mac's has been serving locals and visitors for decades. If you're looking for classic Keys comfort food before continuing your drive south, this is a great place to stop.
Best For
- Breakfast
- Comfort food
- Local history
Don't Miss
- Seafood dishes
- Homemade desserts
- Key lime pie
📍 Islamorada
If you're celebrating a special occasion, Chef Michael's is worth the reservation. Known for elevated Florida Keys cuisine and beautifully prepared local seafood, it's one of the area's most respected restaurants.
Best For
- Date night
- Special occasions
- Local seafood
Don't Miss
- Hogfish (when available)
- Local catch specials
- Florida lobster
Few restaurants capture the laid-back Florida Keys lifestyle better than Lazy Days. Ocean views, fresh seafood, and one of the area's signature fish dishes make this a must-stop while driving through Islamorada.
Best For
- Waterfront dining
- Sunset dinner
- Fresh seafood
Don't Miss
- Lazy Days Style Fish
- Conch fritters
- Key lime pie
📍 Marathon
Porky's Bayside Restaurant & Marina ⭐ Road & Table Favorite
If I had to choose one restaurant in the Florida Keys, it would be Porky's.
Between the marina views, relaxed atmosphere, live music, and fresh seafood, this is exactly what I picture when I think about dining in the Keys. After a day at Bahia Honda or snorkeling at Sombrero Reef, there's no better place to unwind.
Best For
- Waterfront dining
- Casual dinner
- Sunset cocktails
Don't Miss
- Fresh catch of the day
- Fish tacos
- Pulled pork
- Frozen Key Lime Pie
Part seafood market, part marina, and part waterfront restaurant, Keys Fisheries has become one of the most iconic seafood stops in the Florida Keys.
The seafood couldn't be fresher, and if it's your first visit, the famous Lobster Reuben is practically a rite of passage.
Best For
- Fresh local seafood
- Casual waterfront dining
- Lunch after Sombrero Reef
Don't Miss
- Lobster Reuben
- Stone crab (seasonal)
- Peel-and-eat shrimp
📍 Key West
No trip to Key West feels complete without a meal at Blue Heaven.
Set in a colorful open-air courtyard, this iconic restaurant is known for its unforgettable breakfasts, Caribbean-inspired dishes, and legendary Key lime pie. It's one of those places that's worth the wait.
Best For
- Breakfast or brunch
- Key lime pie
- Classic Key West atmosphere
Don't Miss
- Lobster Benedict
- Banana pancakes
- Key lime pie
For a truly unforgettable dining experience, book dinner at Latitudes on Sunset Key. Accessible only by ferry, it's one of the most romantic restaurants in the Florida Keys and offers incredible waterfront views.
Best For
- Anniversary dinners
- Romantic evenings
- Sunset dining
Don't Miss
- Fresh local seafood
- Seasonal chef's specials
- Sunset cocktails
If you're looking for something beyond seafood, Santiago's Bodega is one of Key West's best-kept dining secrets. Their Spanish-inspired tapas menu is perfect for sharing and offers a welcome change of pace during your trip.
Best For
- Tapas
- Sharing plates
- Dinner with friends
Don't Miss
- Bacon-wrapped dates
- Beef tenderloin
- Seasonal tapas specials
What to Eat in the Florida Keys
No matter where you choose to dine, be sure to try a few local specialties during your trip.
- Florida lobster (seasonal)
- Stone crab claws (October through May)
- Fresh mahi-mahi
- Yellowtail snapper
- Conch fritters
- Key West pink shrimp
- Lobster Reuben
- Authentic Key lime pie
5-Day Florida Keys Road Trip Itinerary
Day 1: Arrive in the Florida Keys
Morning
- Arrive in Miami or Fort Lauderdale
- Pick up your rental car
- Begin the scenic drive down the Overseas Highway
Afternoon
- Lunch at Hobo's Café in Key Largo
- Stop at Anne's Beach or enjoy one of the scenic overlooks along the Overseas Highway
- Continue to Marathon and check into your hotel
Where to Stay
⭐
Road & Table Pick: Isla Bella Beach Resort
Dinner
🍽️ Porky's Bayside Restaurant & Marina
Don't Miss
- Your first drive along the Overseas Highway
- Seven Mile Bridge at sunset
- Marina views from Porky's
Road & Table Tip: Resist the urge to cram too much into your arrival day. The drive is part of the experience, so take your time and enjoy the journey south.
Day 2: Snorkeling & Bahia Honda
Morning
- Snorkeling excursion with Spirit Snorkeling
- Explore Sombrero Reef
Afternoon
- Relax at Bahia Honda State Park
- Swim at Sandspur Beach
- Return to Isla Bella to unwind
Dinner
🍽️ Keys Fisheries
Don't Miss
- Sombrero Reef
- Sandspur Beach
- Old Bahia Honda Bridge
Road & Table Tip: This was my favorite day of the trip. If you only splurge on one excursion, make it snorkeling at Sombrero Reef.
Day 3: Marathon to Key West
Morning
- Enjoy a leisurely breakfast at Isla Bella
- Relax by the pool or beach before checking out
Afternoon
- Drive the scenic Overseas Highway to Key West
- Check into your hotel
- Explore Duval Street, the Historic Seaport, and Mallory Square
Where to Stay
- Luxury: Ocean Key Resort & Spa
- Boutique: The Gardens Hotel
- Historic Charm: Kimpton Winslow's Bungalows
Dinner
🍽️ Latitudes (reserve well in advance)
Don't Miss
- Mallory Square Sunset Celebration
- Historic Seaport
- Duval Street
Road & Table Tip: Take your time driving into Key West. There are plenty of scenic pull-offs and photo opportunities along the way.
Day 4: Explore Key West
Morning
- Breakfast at Blue Heaven
- Visit the Ernest Hemingway Home & Museum
Afternoon
- Relax at Fort Zachary Taylor Historic State Park
- Browse local boutiques and art galleries
Dinner
🍽️ Santiago's Bodega
Don't Miss
- Southernmost Point
- Fort Zachary Taylor Beach
- Key lime pie from Blue Heaven
Road & Table Tip: Venture a few blocks beyond Duval Street to discover quieter neighborhoods, local cafés, and hidden gems that many visitors miss.
Day 5: One Last Taste of Paradise
Morning
- Enjoy a slow breakfast
- Pick up a few local souvenirs
- Take one last stroll along the waterfront
Afternoon
- Fly home from Key West (recommended) or begin the drive back to Miami or Fort Lauderdale
Don't Miss
- One last slice of authentic Key lime pie
- Waterfront views before you leave
Road & Table Tip: If your budget allows, book an open-jaw flight—fly into Miami or Fort Lauderdale and home from Key West. You'll save yourself the four-hour drive back to the mainland and gain valuable vacation time.
With two nights in Marathon and two nights in Key West, you'll experience two completely different sides of the Florida Keys. Marathon offers laid-back beaches, world-class snorkeling, and a slower pace, while Key West brings history, nightlife, and some of the best dining in the islands. Together, they create the perfect five-day road trip—one that's filled with unforgettable meals, incredible scenery, and plenty of time to simply enjoy the journey.
Ready to experience the Keys the Road & Table way?
👉 Let me design your food-first Florida Keys itinerary—complete with hidden gems, must-reserve restaurants, and a fully curated travel guide delivered before you go. Contact me HERE!
Jamie Cassidy – Founder & Travel Designer at Road & Table
Jamie Cassidy is the founder and travel designer behind Road & Table — a boutique travel brand curating food-forward journeys and authentic travel experiences around the world. From truffle hunts in Tuscany to oyster farms in Connemara, she believes every road leads to a great table (and an even better story).
© Jamie Cassidy and Road And Table, 2023. Unauthorized use and/or duplication of this material without express and written permission from this site’s author and/or owner is strictly prohibited. Excerpts and links may be used, provided that full and clear credit is given to Jamie Cassidy and Road and Table with appropriate and specific direction to the original content.
