🌿 RelaxedLong weekend · from Orlando, FL

Florida Keys: Key Largo & Islamorada

The Upper Keys begin three and a half hours south of Orlando where US-1 leaves the Florida mainland at Key Largo and the roadway becomes a series of bridges across the turquoise shallows between the Gulf of Mexico and the Atlantic. Key Largo holds the only living coral reef in the continental United States at John Pennekamp State Park. Islamorada, 25 miles south, is the sport-fishing capital of the world and has the best restaurants in the Keys. Three days in the Upper Keys moves at the pace the Keys are designed for: glass-bottom boat in the morning, fish tacos at noon, tarpon feeding at Robbie's Marina in the afternoon, and watching the sun go down over the Gulf from a tiki bar at six.

Day 1 — Key Largo: Pennekamp Reef & Glass-Bottom BoatDay 2 — Islamorada: Robbie's Marina & Backcountry KayakingDay 3 — Sunset Kayak & Drive North

Day 1 — Key Largo

🚗 3 hr 35 min driving📍 5 stops

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Morning

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Drive

Orlando, FL → Key Largo, FL

3 hr 35 min8:00 AM → 11:35 AM

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John Pennekamp Coral Reef State Park

The first undersea state park in the United States, established in 1960 to protect the only living coral reef in the continental US — 70 nautical square miles of reef, seagrass beds, and mangrove hammock. The glass-bottom boat tours depart from the park marina and pass over brain coral, elkhorn coral, and reef fish in water clear enough to read a newspaper through; snorkel and scuba trips go directly to the reef. The park visitor center has a large reef aquarium that gives context before you go out.

11:35 AM📍 See location

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Lunch

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Mrs. Mac's Kitchen

A Key Largo institution on US-1 since 1976 — fish sandwiches, Key lime pie, and seafood baskets in a wood-paneled room papered with license plates from every state in the US. The grouper Reuben is the signature and what you should order; the pie is the real Key lime variety made with actual Key lime juice, pale yellow rather than green.

12:35 PM📍 See location

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Afternoon

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John Pennekamp — Canoe Trail & Mangrove Forest

A 3-mile marked canoe trail through the mangrove interior of the state park — slow and shaded, with snappers and snook in the channels below the roots, great white herons on the exposed prop roots, and the quiet of a mangrove forest that functions as the nursery for the reef you saw this morning. Kayak and canoe rentals available at the park marina; no motorized boats allowed in the mangrove trail.

1:35 PM📍 See location

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Evening

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Snappers Waterfront Restaurant

Dinner on the bay side of Key Largo with a dock and tiki bar directly over the water — freshly caught mahi-mahi, yellowtail snapper, and stone crab claws in season, in a setting where you can watch pelicans land on the dock pilings and the mangrove islands across the channel turn orange at sunset.

5:00 PM📍 See location

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Key Largo Bay Marriott Beach Resort

The best-positioned hotel in Key Largo — on the bay side of the island with a beach, kayak rentals, watersports, and a tiki bar above the water. The sunset from the bay side is the Keys' real show; the Atlantic is where the reef is, but the Gulf side is where the colors are.

6:00 PM📍 See location

Day 2 — Islamorada

🚗 25 min driving📍 5 stops

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Morning

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Drive

Key Largo → Islamorada

25 min8:00 AM → 8:25 AM

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Robbie's Marina — Tarpon Feeding

The most famous dock in the Florida Keys — giant Atlantic tarpon, some over 100 pounds and six feet long, crowd the marina dock to be hand-fed by visitors who buy buckets of baitfish for $5. The tarpon roll on the surface like logs coming to life, and they will take a fish directly from your hand if you have the nerve to hold it at water level. Robbie's also rents kayaks for the Florida Bay backcountry and runs snorkel trips. Come before 11am for the best feeding activity before the boat traffic stirs the fish.

8:25 AM📍 See location

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Lunch

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Lorelei Restaurant & Cabana Bar

Lunch on the Islamorada waterfront with a thatched-roof tiki bar, live music on weekends, and a menu built around local fish — the yellowtail snapper, caught in the waters directly visible from your table, is the right order. The bay-side deck puts you exactly where the Keys are supposed to make you feel.

9:25 AM📍 See location

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Afternoon

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Florida Bay Backcountry Kayaking — Islamorada

Paddle the shallow backcountry flats of Florida Bay from one of the outfitters near Robbie's — clear water one to three feet deep over white sand and seagrass, with bonefish tailing in the shallows, spotted eagle rays crossing ahead, and the silence of a wilderness accessible only by kayak. The 'backcountry' is the name for the shallow bay side of the Keys; it is the opposite experience from the reef and equally remarkable.

12:00 PM📍 See location

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Evening

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Morada Bay Beach Café

The best dinner in Islamorada on the beach, in the sand, with tiki torches lit at sunset and tables directly above the water — Caribbean-influenced cooking from Keys-sourced fish and local produce that matches the setting. The monthly Full Moon Party here is a Keys institution; on any evening the sunset from this beach is the definitive Keys experience.

5:00 PM📍 See location

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Cheeca Lodge & Spa

The iconic Islamorada resort, operating since 1946 — a private beach, fishing pier, dive operation, pools, and the Atlantic Ocean. The most complete resort property in the Upper Keys, completely renovated in recent years and sitting on the best oceanfront lot in Islamorada. Presidents have fished here; so has everyone else.

6:00 PM📍 See location

Day 3 — Islamorada — Morning Snorkel & Drive North

🚗 3 hr 55 min driving📍 3 stops

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Morning

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Drive

Cheeca Lodge → Theater of the Sea

10 min8:00 AM → 8:10 AM

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Anne's Beach & Indian Key

A final morning at Anne's Beach on Lower Matecumbe Key — a shallow, calm tidal flat backed by red mangroves, with a boardwalk through the wetland and warm, clear water that is only knee-deep for 100 feet out. The whole Key of Indian Key is visible offshore — a 12-acre uninhabited island where an 1840 Seminole raid destroyed a village that had 50 permanent residents and a post office. Kayak tours reach the island from Robbie's Marina.

8:10 AM📍 See location

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Lunch

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Whale Harbor Restaurant

An Islamorada institution at mile marker 83.5 with a waterfront deck above the Atlantic — fresh grouper, snapper, and Keys seafood in a no-pretense room that has been feeding anglers and divers since it opened. The seafood buffet on weekends draws the whole island.

9:10 AM📍 See location

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Afternoon

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Drive

Islamorada, FL → Orlando, FL

3 hr 45 min12:00 PM → 3:45 PM

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Evening

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Robert Is Here — Homestead Stop

A final stop on the US-1 to turnpike transition in Homestead — the tropical milkshake stand that has been drawing travelers off the road since 1959. The Keys-to-Orlando drive passes directly through Homestead; this is a 10-minute detour that most people who stop here once stop at every subsequent time they make this drive.

5:00 PM📍 See location

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