A Florida Keys road trip is one of the most iconic drives in the United States. In 2026, the experience is even better — smoother roads, upgraded parks, and a growing focus on slow, scenic travel. This itinerary is designed for travelers who want clear water, island vibes, great food, and unforgettable sunsets, without rushing.
This is the ultimate Florida Keys road trip itinerary for 2026, starting from the mainland and ending at the edge of America.
Overview: Florida Keys Road Trip at a Glance
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Total distance: ~113 miles
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Best length: 4–6 days
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Start: Florida City / Key Largo
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End: Key West
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Best time in 2026: February–May, late October–early December
You’ll drive the legendary Overseas Highway (US-1) — one of the most scenic roads in the country.
Day 1: Key Largo — Coral Reefs & Easy Island Start
Key Largo is the perfect gateway to the Keys.
What to Do
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Snorkel or glass-bottom boat at John Pennekamp Coral Reef State Park
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Kayak through mangroves
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Relax — don’t overpack your first day
Where to Eat
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Waterfront seafood shacks
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Fresh fish sandwiches and key lime pie
Stay the Night
Key Largo or nearby Tavernier — calm, uncrowded, and ideal for easing into island time.
Day 2: Islamorada — Laid-Back Luxury & Water Life
Islamorada feels like the heart of the Keys.
Highlights
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Visit the iconic Theater of the Sea
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Paddleboard or snorkel offshore
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Sunset drinks overlooking the water
Must-Do Stops
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Robbie’s Marina (tarpon feeding)
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Small art galleries and beach bars
Islamorada is perfect if you want luxury without crowds.
Day 3: Marathon — Bridges, Turtles & Island History
Marathon sits in the Middle Keys and makes a great base.
What to See
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Seven Mile Bridge — stop at viewpoints for photos
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Turtle Hospital (educational & meaningful)
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Local beaches and casual waterfront dining
Pro Tip
Drive the bridge early morning or near sunset for fewer cars and better light.
Day 4: Bahia Honda State Park — Best Beach in the Keys
This is a non-negotiable stop on any Florida Keys road trip itinerary.
Why It’s Special
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Soft sand (rare in the Keys)
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Turquoise water
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Views of the old railroad bridge
What to Do
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Swim or snorkel
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Picnic lunch
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Short nature trails
Arrive early — parking fills fast, even in 2026.
Day 5: Key West — Culture, Color & Sunsets
Key West is vibrant, historic, and unforgettable.
Must-See Spots
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Southernmost Point
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Duval Street (daytime strolling)
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Historic Old Town neighborhoods
Sunset Ritual
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Mallory Square for street performers and sunset celebrations
Nightlife
Key West evenings are relaxed but lively — live music, open-air bars, and ocean breezes.
Optional Day 6: Slow Down or Go Offshore
If you have extra time:
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Snorkeling or reef tour
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Dry Tortugas day trip (weather permitting)
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Extra beach day or food crawl in Key West
This buffer day turns a good trip into a great one.
Where to Stay Along the Way
Best strategy: Stay in 2–3 places max.
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Key Largo / Islamorada (Upper Keys)
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Marathon (Middle Keys)
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Key West (Lower Keys)
This minimizes packing and maximizes relaxation.
Driving Tips for the Florida Keys (2026)
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Speed limits are enforced — drive slow
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Fuel up before long stretches
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Avoid night driving if possible (wildlife crossings)
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Download offline maps (cell service can drop)
The drive is part of the experience — don’t rush it.
What to Pack
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Reef-safe sunscreen
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Snorkel gear (rentals are expensive)
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Light layers for evenings
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Water shoes
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Reusable water bottles
Travel light — island life is simple.
Best Time for a Florida Keys Road Trip in 2026
🌤 Best: February–May (dry, warm, breezy)
🌴 Good: November–early December
⚠️ Avoid: Peak hurricane season (late August–September)
Final Thoughts
The ultimate Florida Keys road trip itinerary for 2026 is not about checking boxes — it’s about slowing down, chasing sunsets, and enjoying the space between islands. From coral reefs in Key Largo to the colorful streets of Key West, this drive delivers freedom, beauty, and unforgettable coastal energy.
Take it slow.
Stop often.
And let the road lead you south.
