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🥾 ActiveWeekend · from Miami, FL

Keys Active: Reef Diving, Flats Fishing & a Sunken Island

Two days of serious outdoor sport in the Upper Keys, where the Atlantic Ocean meets Florida Bay across a chain of islands barely above sea level. Day one takes you underwater at John Pennekamp — snorkeling the living reef and kayaking mangrove tunnels. Day two heads to the backcountry: a guided flats fishing charter for bonefish and permit on the legendary Florida Bay flats, and a boat trip to Indian Key — a 10-acre island that was briefly the seat of Dade County in the 1830s, burned by Seminoles in 1840, and is now accessible only by kayak or water taxi.

Day 1 — Key Largo, FLDay 2 — Islamorada, FL
Day 1Key Largo, FL

Day 1Key Largo, FL

🚗 1 hr 30 min driving📍 5 stops
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Morning
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Drive
Miami, FLJohn Pennekamp Coral Reef State Park, Key Largo
1 hr8:00 AM9:00 AM
John Pennekamp — Snorkel Tour, Molasses Reef
John Pennekamp — Snorkel Tour, Molasses Reef
4.5
The morning snorkel trip to Molasses Reef — one of the most visited dive sites in the world and one of the healthiest sections of the Florida Reef — departs at 9am. The reef rises to within 10 feet of the surface at its shallowest points and drops to 35 feet at its deepest edges, providing snorkelers and divers with close encounters with the full suite of Caribbean reef fish: sergeant majors, yellowtail snapper, blue tangs, parrotfish, and the occasional sea turtle resting on the bottom. The Pennekamp reef is unusual in that its protected status since 1963 has allowed coral to recover from some of the bleaching events that devastated unprotected sections of the Florida Reef. Book in advance — the 9am trip sells out every weekend.
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Lunch
🍽️ Lunch10:00 AM
Fish House Restaurant
Fish House Restaurant
The best local seafood lunch in Key Largo — conch fritters, blackened mahi, fresh stone crab in season — from a no-frills restaurant that buys from Keys fishermen daily. Post-snorkel hunger demands quantity and quality; this delivers both.
4.5$$seafood restaurant📍 Maps →
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Afternoon
Continue at John Pennekamp — North Sound Creek Mangrove Kayak
Continue at John Pennekamp — North Sound Creek Mangrove Kayak
4.5
Use the afternoon to explore a different trail, cool off at a swimming hole, or find a scenic spot to watch the sunset.
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Evening
🚗
Drive
Key LargoIslamorada, FL
30 min5:00 PM5:30 PM
🍽️ Dinner5:30 PM
Morada Bay Beach Cafe — Sunset Dinner
Morada Bay Beach Cafe — Sunset Dinner
Barefoot on Florida Bay with the sun dropping behind the mangroves — the classic Islamorada dinner setting, with Caribbean-inflected seafood and cold drinks at outdoor tables on the sand.
4.4$$american restaurant📍 Maps →
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Cheeca Lodge & Spa
Islamorada's historic oceanfront resort with a fishing pier, 1,100-foot private beach, full spa, and direct Florida Keys atmosphere. The best base for an early fishing charter departure the next morning.
Day 2Islamorada, FL

Day 2Islamorada, FL

🚗 1 hr 30 min driving📍 3 stops
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Morning
Islamorada Backcountry Fishing Charter
Islamorada Backcountry Fishing Charter
4.1
Islamorada is the self-styled 'Sport Fishing Capital of the World' — a claim grounded in the extraordinary fishing available in the Florida Bay backcountry, where shallow grass flats extending 35 miles toward the Everglades support world-class populations of bonefish, permit, and tarpon. A half-day flats fishing charter (4-5 hours) departs at 7am and poles the skiff through knee-deep water, sight-fishing to individual fish — the guide spots them from the polling platform before casting distance, and you cast precisely. Bonefish and permit are renowned as among the most challenging light-tackle targets in the world: they spook easily, require accurate casting, and run explosively when hooked. This style of fishing, called 'flats fishing' or 'sight fishing,' originated in the Florida Keys and is now practiced worldwide; the Keys remains its spiritual home. Book through Bud n' Mary's Marina (MM 79.8), the oldest fishing marina in the Keys.
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Lunch
🍽️ Lunch9:00 AM
Hungry Tarpon at Robbie's Marina
Hungry Tarpon at Robbie's Marina
Lunch at Robbie's — the open-air restaurant at the famous marina where giant tarpon gather at the dock. Order the grilled yellowtail and watch 100-pound tarpon compete for scraps at your feet. This is one of the more surreal dining experiences in Florida.
4.4$$seafood restaurant📍 Maps →
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Afternoon
Indian Key Historic State Park
Indian Key Historic State Park
4.6
Indian Key is a 10-acre island accessible only by water — kayak from Anne's Beach or water taxi from Robbie's Marina — that served as the seat of Dade County in the 1830s under the ownership of wrecker Jacob Housman. The island had a hotel, post office, store, and a population of about 60 when Seminole warriors paddled from the mainland on August 7, 1840, at 2am in a raid that killed Housman's partner Dr. Henry Perrine (a botanist who had introduced sisalhemp to Florida) and drove the settlers into the ocean. Housman escaped by swimming. The island was never resettled and today only stone ruins remain — the ghost of a would-be 19th-century Keys city, surrounded by buttonwood and cactus. Naturalist John James Audubon visited the island in 1832 and recorded several previously unknown bird species from its waters.
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Evening
🚗
Drive
Islamorada, FLMiami, FL
1 hr 30 min5:00 PM6:30 PM
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