Miami to Key West in One Day: The Overseas Highway

The Overseas Highway is more about the road than the destination, and this plan treats it that way: a single, full day, four stops, and a lot of open water in between. You leave downtown Miami at 8:15 on a toll road, stop in Homestead for a fruit-stand milkshake just after the 9 am opening, and then U.S. 1 narrows to two lanes and starts to look like nothing else in the country: mangrove on both sides, then open water, then a long ribbon of bridges. Once you reach Key Largo, the green mile markers count down to 0 at the far end in Key West.

The stops earn their place. Robert Is Here, family-run in Homestead since 1959 by its own account, is the classic warm-up. Robbie's Marina in Islamorada, at about mile marker 77.5, is where dozens of tarpon gather under the dock and take bait fish from your hand; the waterfront Hungry Tarpon restaurant on the same property is the lunch stop, so there is no extra hunt for a table. After that comes the drive's showpiece, the Seven Mile Bridge, and Bahia Honda State Park, whose 2.5-mile beach and piece of Henry Flagler's railroad bridge are the best swim-and-photo stop on the highway. Then it is the last hour into Key West and Mallory Square for the nightly Sunset Celebration.

Why a single day works. The whole route is 229 minutes of pure driving, well under the roughly eight hours that would call for a second day. The catch is that Mallory Square needs to happen before dark: sunset is about 6:21 pm in mid-February and after 7:30 pm from mid-March, so the plan is built for February to April. In December and January, with sunsets before 6 pm, you would have to skip a stop. Anyone who would rather sleep in the Keys will find places to stay in Islamorada in the options, along with extra stops (John Pennekamp Coral Reef State Park, The Turtle Hospital, Mrs. Mac's Kitchen, No Name Pub, the Hemingway Home) that you can swap in if you leave earlier or stay a night.

Which way in? US-1 is the recommended way: no bridge toll, shorter and quicker than Card Sound Road on Google's numbers, and every stop is on it. Card Sound Road is the scenic alternate (with Alabama Jack's), noted in the options.

The totals across the 4 driving legs add up to 169.7 miles, 229 minutes (3h 49m) of pure driving and $5.95 in estimated tolls on a toll-by-plate basis (about $3.41 with a SunPass), all on the first leg out of Miami.

Route, timing and weekday assumptions

• Assumed weekday: a Saturday departure. Robert Is Here (official: 9 am to 6 pm daily), Robbie's (marina 7 am to 9 pm, Hungry Tarpon 6:30 am to 9 pm daily) and Bahia Honda (8 a.m. until sundown) are all open at the scheduled times.
• Departure: 8:15 am from Miami so you reach Robert Is Here just after it opens at 9. This is a long day: about 229 minutes of driving plus about 6 hours 30 minutes at stops (including free time in Old Town before sunset), ending near 6:30 pm at Mallory Square. If you add an optional stop (John Pennekamp or the Turtle Hospital), leave earlier or expect to arrive after sunset in February.
• Totals: 169.7 miles, 229 minutes (3h 49m) of pure driving, $5.95 in estimated tolls (toll-by-plate basis; about $3.41 with SunPass). Drive times come from the Google Routes API without live traffic; US-1 is mostly a two-lane road, so an accident or a weekend crowd can add a lot.
• Why US-1 and not Card Sound Road: toll-free, shorter (26.8 vs 32.5 miles from Homestead to Key Largo on Google's numbers), and every stop is on it (see options).
• Paying tolls: all toll roads on leg 1 are electronic (no cash). The trip total of $5.95 is on a Toll-By-Plate basis (billed to the registered owner; rental cars usually pass it through the rental company); with a SunPass the same route is about $3.41. It breaks down as SR 836 $2.64 + SR 874 $1.86 (GMX schedule, whose PDF carries 2023-2024 dates, so confirm current rates on gmx-way.com) + Florida's Turnpike Homestead Plaza $1.45 by plate ($1.16 SunPass, effective 2026-04-21) = $5.95.
• Return: this is a one-way itinerary. To go back to Miami take US-1 north: Google shows about 165.1 miles and 3h32m with a $5.95 estimated toll if it uses the Turnpike, or about 160.1 miles and 4h09m toll-free (computed 2026-09-29). Key West also has an airport (EYW) if you prefer to fly, or you can stay a night (see the places to stay in the options).
• Sunsets (approximate, NOAA solar equations for Key West, +/-3 min): Feb 15 ~6:21 pm, Mar 15 ~7:36 pm, Apr 15 ~7:49 pm (daylight saving time from mid-March); for reference Dec 21 ~5:43 pm and Jan 15 ~5:59 pm. The plan reaches Key West about 3:50 pm; in March and April there is over an hour of extra light, so add time at Bahia Honda or in Old Town. Islamorada's sunset is a few minutes earlier than Key West's.
• Best months: February to April. Dec/Jan sunsets (before 6 pm) do not fit this timed one-day plan without dropping a stop.
• Parking: in Key West park once (paid lots and limited street spaces; rates not verified) and walk; Mile Marker 0, the Hemingway Home, Kermit's and Mallory Square are within about a mile.
• Fees (as of 2026-09-29): Robbie's tarpon feeding $2.50 per person plus $5 per bucket of fish; Bahia Honda $8 per vehicle. Optional stops: Pennekamp $8 per vehicle plus 50 cents per person; Turtle Hospital $38 adult (reserve a slot); Hemingway Home $19 adult.