option 10 of 10 — the island road trip
Florida Keys
Miami to Key West, USA
Top down on the Overseas Highway — 113 miles of bridges over turquoise water.
Estimated Cost
$3,600 – $4,500
Length
7 Days / 6 Nights
Getting There
~3.5 hrs from Minneapolis (MSP → MIA)
Best Time to Go
December – April
The Trip
America's most beautiful drive: fly to Miami, put the top down, and island-hop 113 miles down the Overseas Highway — snorkeling America's only living coral reef, crossing the Seven Mile Bridge, and ending in Key West for sunset celebrations and key lime pie.
The Real Budget
For both of us, flights from Minneapolis included. Prices are realistic planning estimates — exact fares move with the season.
| Item | Details | Cost |
|---|---|---|
| Round-trip flights | MSP → Miami, 2 travelers | $600 |
| Convertible rental & gas | 7 days — the Overseas Highway demands it | $450 |
| Lodging | 2 nights Islamorada + 4 nights Key West guesthouse (~$230/night) | $1,380 |
| Food & drinks | Fish shacks, raw bars, key lime everything (~$120/day) | $840 |
| Coral reef snorkel trip | John Pennekamp reef boat, for two | $130 |
| Key West sunset sail | Champagne catamaran, for two | $160 |
| Old Town sights | Hemingway House + lighthouse + museums | $60 |
| Bahia Honda beach day | Park entry + kayak rental | $80 |
| Souvenirs & wiggle room | A regrettable tropical shirt each | $150 |
| Estimated total for two | $3,850 | |
| Comfortably under our $5,000 budget — $1,150 of breathing room for spontaneous ice cream. | ||
Where We'd Stay
Real places, checked against the budget — tap any of them to look around.
Islamorada
Amara Cay Resort
Laid-back oceanfront resort
Oceanfront in the heart of Islamorada for the first two nights of the drive south.
Visit their site ↗Old Town, Key West
Eden House
Historic garden guesthouse
Key West's classic garden hideaway — hammocks, a heated pool, and porch swings, blocks from Duval.
Visit their site ↗Our Week, Day by Day
Day 1Miami & the art deco warm-up
Morning flight to Miami, pick up the convertible, and ease in with an afternoon on South Beach — art deco architecture, Cuban coffee, and dinner on Ocean Drive.
Moment of the day: Cafecito standing at a Calle Ocho window
Day 2Into the Keys — Islamorada
Top down, heading south: the mainland falls away and the water turns impossible shades of blue. Land in Islamorada, 'sportfishing capital of the world,' for a dockside dinner as tarpon roll under the lights.
Moment of the day: The first bridge where it's water on both sides
Day 3Snorkel the living reef
Morning boat from John Pennekamp State Park out to America's only living coral barrier reef — parrotfish, angelfish, and the famous underwater Christ statue — then a lazy waterfront afternoon.
Moment of the day: Hovering over the reef in ten feet of clear water
Day 4Seven Mile Bridge to Key West
The drive of a lifetime: Bahia Honda's white-sand beach for a swim and kayak, over the Seven Mile Bridge, and into Key West by golden hour for the Mallory Square sunset celebration.
Moment of the day: Crossing Seven Mile Bridge with the top down
Day 5Old Town Key West
Breakfast at a porch café, Hemingway's house and the six-toed cats, the Southernmost Point buoy, an afternoon at the pool, and Duval Street after dark.
Moment of the day: Arguing about which six-toed cat is best
Day 6Sunset sail & the last night
Slow island morning, an afternoon champagne catamaran sail as the sun drops into the Gulf, and a final anniversary dinner in a garden courtyard under the palms.
Moment of the day: Champagne on deck as the sky goes pink
Day 7Key lime pie for the road
One last café con leche and a slice of key lime pie (for breakfast — we're on vacation), then the beautiful drive back up the Keys to Miami for the evening flight home.
Moment of the day: Pie for breakfast, zero regrets
is it this one?
Compare them all, or peek at the next option.
Destination photography via Wikimedia Commons — photo credits.