The Florida Keys in three days: a backroad run down Card Sound Road to a legendary conch-fritter roadhouse, a night in Islamorada’s marina-front resorts, a swim stop at Bahia Honda’s old railroad bridge before crossing Seven Mile Bridge, and a final full day in Key West between the Southernmost Point buoy, Hemingway’s house, and the nightly sunset celebration at Mallory Square — with real hotels, real roadside restaurants, and 2026 prices for every stop.
Day 1
Miami to Islamorada
Pick up a rental car in Miami and take the backroad option south — Card Sound Road instead of the main highway — for a first Keys meal at a legendary roadhouse before settling into Islamorada for the night.
🚗 Rental Car Pickup — Miami International Airport
~15 minutes · From $55 USD / day, economy car
Every major agency operates out of Miami International Airport’s rental car center; a two-door or small SUV is plenty for the two-lane drive south.
🍽️ Lunch — Alabama Jack’s
~1 hour · $12–$18 USD / person, seafood shack
A floating-dock roadhouse on Card Sound Road serving Keys-famous conch fritters and cold beer to a crowd of bikers, boaters, and weekend drivers, with mullet skipping in the water below the deck.
Alabama Jack’s · 58000 Card Sound Rd, Key Largo, FL 33037
🐢 Florida Keys Wild Bird Center Stop
~45 minutes, self-guided · Free (donations welcome)
A boardwalk through a mangrove hospital for injured pelicans, herons, and ospreys sits just off the highway in Tavernier, a quick leg-stretch on the drive to Islamorada.
🌅 Sunset Dinner — Morada Bay Beach Café
~1.5 hours · $30–$45 USD / person, waterfront Caribbean
Tables set directly in the sand face open water on the bay side of Islamorada, timed for a sunset that regularly draws a crowd for the view alone.
Morada Bay Beach Café · 81600 Overseas Hwy, Islamorada, FL 33036
🛎️ Overnight — Three Waters Resort and Marina, Islamorada
From $260 USD / night, for 2 people
A marina-front resort (a Tribute Portfolio Resort) with a private sandbar beach and boat slips, centrally placed for exploring Islamorada’s dive shops and sportfishing docks.
Three Waters Resort and Marina, Islamorada · 84001 Overseas Hwy, Islamorada, FL 33036 · marriott.com/miatw
Day 2
Islamorada to Key West
A late-morning swim stop at a state park built around an abandoned railroad bridge, the long crossing of Seven Mile Bridge, and a first evening in Key West’s old town.
🏖️ Bahia Honda State Park
~2 hours, self-guided · $8 USD per vehicle (up to 8 people)
Widely rated the best beach in the Keys, with sandbar-shallow turquoise water and a walkable stretch of the original 1912 Overseas Railroad bridge rising from the water beside the current highway.
🌉 Drive — Seven Mile Bridge
~15 minutes, self-drive · Free
The Overseas Highway’s signature crossing runs open water for nearly seven miles between Knight’s Key and Little Duck Key, with the old bridge’s ruins running alongside for photos.
🍽️ Lunch — Mrs. Mac’s Kitchen
~1 hour · $12–$20 USD / person, roadside diner
A Key Largo institution since 1976 (worth the backtrack, or a stop on the way down) — hubcaps cover the walls and the conch chowder and key lime pie are local benchmarks either way.
Mrs. Mac’s Kitchen · 99336 Overseas Hwy, Key Largo, FL 33037 · (305) 451-3772
🎉 Mallory Square Sunset Celebration
~1.5 hours, self-guided · Free
A nightly street-performer festival — jugglers, tightrope walkers, a bagpiping unicyclist most nights — gathers on the waterfront to applaud the sunset behind the harbor’s moored sailboats.
🛎️ Overnight — Southernmost Beach Resort
From $340 USD / night, for 2 people
A beachfront resort at the foot of Duval Street, close enough to walk to Old Town’s restaurants and the Southernmost Point buoy.
Southernmost Beach Resort · 1319 Duval St, Key West, FL 33040 · (305) 296-6577 · southernmostbeachresort.com
Day 3
Key West & the Drive Home
A morning among Key West’s landmarks — the Southernmost Point, Hemingway’s six-toed cats, a Cuban-toast breakfast — before the long drive back up the Overseas Highway to Miami.
📸 Southernmost Point Buoy
~20 minutes, self-guided · Free
The red-and-black concrete buoy marking the continental United States’ southernmost point is Key West’s most-photographed landmark, best visited early before the tour-group lines form.
🐈 Ernest Hemingway Home & Museum
~1 hour, self-guided · ~$18 USD entrance
The Spanish Colonial house where Hemingway wrote ‘A Farewell to Arms’ still shelters dozens of six-toed cats descended from his own, roaming a lush garden a short walk from the lighthouse.
Ernest Hemingway Home & Museum · 907 Whitehead St, Key West, FL 33040 · (305) 294-1136
🍽️ Breakfast — Blue Heaven
~1 hour · $15–$22 USD / person, Key West brunch classic
Roosters wander a plant-filled courtyard once used for Hemingway-era boxing matches, while the kitchen turns out banana pancakes and Cuban-toast French toast that draw a line most mornings.
Blue Heaven · 729 Thomas St, Key West, FL 33040 · (305) 296-8666 · blueheavenkw.com
🚗 Drive — Key West to Miami International Airport
~3.5 hours, self-drive · Rental car already in hand
The return drive retraces the Overseas Highway north across all 42 bridges, timed for an evening flight out of Miami.
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