This is the longest of our rides and the classic South Florida road trip: door to door down the Overseas Highway, the string of bridges and islands officially known as US-1, with an early start to make the most of the day. The drive down passes through Key Largo, Islamorada and Marathon, crossing the Seven Mile Bridge with open water on both sides, and stops wherever you would like to slow down for photos.
In Key West, the afternoon covers the island's best-known points: the Southernmost Point buoy, the shops and bars of Duval Street, Mallory Square by the water and the outside of the Hemingway Home. There is time for lunch and, before heading back, a slice of key lime pie, as much a Key West tradition as the sunset itself.
Because this is your car for the day, the schedule is yours to set: leave Key West when you are ready rather than at a set time, and decide how long to spend at each stop along the way. Most guests are back in Miami in the evening, tired from a long but easy day on the road.
Highlights
- Early start down the Overseas Highway (US-1)
- Key Largo, Islamorada and Marathon along the way
- Crossing the Seven Mile Bridge over open water
- Photo stop at the Southernmost Point buoy
- Duval Street and Mallory Square in Key West
- A pass by the outside of the Hemingway Home
- A slice of Key West's classic key lime pie
- Your own schedule for the drive back
Itinerary
- 1
Early pickup
An early pickup so the whole day is ahead of you on the drive south.
- 2
Key Largo to Marathon
The drive down the Overseas Highway through Key Largo, Islamorada and Marathon, with stops where you like.
- 3
Seven Mile Bridge
A crossing of the Seven Mile Bridge, with water stretching to the horizon on both sides.
- 4
Arrival in Key West
Arrival on the island and a stop at the Southernmost Point buoy.
- 5
Duval Street and Mallory Square
Time to walk Duval Street and Mallory Square, with lunch and a slice of key lime pie.
- 6
Hemingway Home
A stop outside the Hemingway Home before the return drive begins.
- 7
Return to Miami
The drive back up the Keys, on your own schedule, arriving in the evening.
Included
- Private car and driver-guide for the full day
- Pickup and drop-off where you are staying
- Bottled water on board
- Photo stops along the Overseas Highway
- Time to walk around in Key West
Not included
- Lunch and key lime pie
- Entrance to the Hemingway Home, if you choose to go in
- Any shopping on Duval Street
- Parking fees, if any
- Gratuity for your driver-guide
Good to know
- A long day — comfortable clothing is recommended
- Sunscreen and a hat for time outdoors in Key West
- The early start can be adjusted within reason
- A good ride for a milestone occasion or a full free day
- Suitable for most ages, with breaks along the way
- Tell us if you want more time in the Upper or Middle Keys instead of Key West itself
FAQ
How early does the day start
Early enough to leave a full day in Key West, typically first thing in the morning. Tell us your preference and we will plan the pickup time around it.
Can we shorten the day and skip Key West itself
Yes. Some guests prefer a shorter round trip that turns back partway down the Keys — let us know and we will adjust the route and time.
Is this trip tiring
It is a long day in the car, though the seats, air conditioning and stops along the way make it comfortable. Many guests rest on the drive back.
Can we stay later in Key West and come back after dark
Yes, within reason. Since you set the schedule, you can stay for sunset at Mallory Square and start the drive back afterward.
