
Day 01
Miami arrival and South Beach
Ease into the journey on Ocean Drive, with time to settle in and explore South Beach at your own pace.
Arrive in Miami and settle into South Beach

This compact Florida journey changes character naturally: Art Deco Miami gives way to the Overseas Highway, Islamorada’s reflective history and Key West’s singular mix of architecture, literature and sea-bound adventure.
Introduction
A sunlit drive from Miami’s Atlantic edge through the Florida Keys to Key West, balancing South Beach style with island history, open-water horizons and the character of Old Town. The journey returns to Miami after three unhurried nights at the end of the Overseas Highway.
Before You Go
Language
English
Currency
US Dollar
Electricity
120V • Type A/B
Cards
Accepted
Entry
VISA • ESTA
Driving License
Recommended
Wayfinding
The Journey

Day 01
Ease into the journey on Ocean Drive, with time to settle in and explore South Beach at your own pace.
Arrive in Miami and settle into South Beach

Day 02
Move from Vizcaya's formal gardens and Biscayne Bay setting to the living cultural fabric of Little Havana.

Day 03
Follow the Overseas Highway south, pausing at the Florida Keys Memorial before reaching Key West for sunset at Mallory Square.
From Miami Beach to Islamorada, Village of Islands, then to Key West
Self-drive
Self-drive
The Betsy – South Beach → Florida Keys Memorial
Self-drive
Florida Keys Memorial → La Concha Key West

Day 04
A walkable day through Key West's literary, presidential and island history, with an easy local dining stop.

Day 05
Set aside the full day for the offshore crossing to Fort Jefferson and return to the Historic Seaport for a relaxed evening.

Day 06
Begin with Fort Zachary Taylor before retracing the Overseas Highway to Miami for a final South Beach night.
From Key West to Miami Beach
Self-drive
Self-drive
La Concha Key West → Fort Zachary Taylor Historic State Park
Self-drive
Fort Zachary Taylor Historic State Park → The Betsy – South Beach

Day 07
Check out after breakfast and continue with your onward travel arrangements.
Selected Stays

The Betsy – South Beach
2 nights

La Concha Key West
3 nights
Don't Miss
01
South Beach energy balanced by Vizcaya’s formal gardens and Little Havana’s cultural life.
02
A gradual transition from mainland city to the island chain, with a meaningful pause in Islamorada.
03
Enough time for Old Town, the island’s historic landmarks and a full-day Dry Tortugas excursion.
04
The same Miami hotel bookends the road trip, keeping arrival and departure straightforward and editable.
Good To Know
Yes. The route is designed around an independently arranged vehicle; rental terms, fuel, parking and tolls are not included or priced in the Journey.
No. The canonical ferry experience is included as an itinerary recommendation, but reservations, operating conditions and supplier availability must be confirmed separately.
Yes. The Betsy and La Concha are editable canonical hotel selections in Journey Builder and can be replaced before publication or when a Program is created.