🌿 RelaxedWeekend · from Miami, FL
Upper Keys Slow Escape: Sunsets, Snorkeling & No Agenda
Two days of deliberate idleness in the Upper Keys — the part of the archipelago that still feels like what the Keys were before they became famous. A morning wading in the shallows at Anne's Beach, an afternoon paddling toward the reef with a snorkel mask in your lap, a sunset from a bayside bar with a cold Kalik in hand, and tarpon feeding chaos at Robbie's dock. No reservations required. No schedule imposed. Just the Keys at their most essentially Keys.
Day 1 — Key Largo, FLDay 2 — Islamorada, FL
Day 1 — Key Largo, FL
Day 1 — Key Largo, FL
🚗 1 hr driving📍 5 stops
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Morning
🚗
Drive
Miami, FL → Key Largo, FL
1 hr8:00 AM → 9:00 AM
🍽️ Breakfast9:00 AM
Mrs. Mac's Kitchen — Breakfast
A Key Largo institution since 1976, Mrs. Mac's Kitchen is a roadside diner with a license plate ceiling, cold draft beer at 8am if you want it, and a menu of conch chowder, eggs benedict with smoked salmon, and fresh-squeezed OJ that announces you have arrived in the Keys. The original location burned and was rebuilt; the spirit has not changed.
2 options · tap to switch
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Lunch
John Pennekamp Coral Reef State Park — Easy Snorkel
★ 4.5For the relaxed version of Pennekamp: skip the boat tour and just rent snorkel gear and wade in at Cannon Beach — a protected lagoon with sandy bottom, clear water, and adequate reef fish and coral without the effort of an organized trip. The 30,000-gallon aquarium in the visitor center gives a preview (or a dry alternative) of what's below the surface. Snorkel gear rentals at the park marina; no boat required.
10:00 AM📍 See location
☀️
Afternoon
Caribbean Club — Afternoon Beer
★ 4.5The Caribbean Club at MM 104 is famous partly because scenes from the 1948 Bogart and Bacall film Key Largo were shot here, and partly because it remains one of the most genuinely Keys-feeling bars still open: a dark, ramshackle waterfront dive with cold beer, a few barstools, and a sunset deck over Florida Bay. The clientele is local fishermen, liveaboards, and people who prefer to avoid anything resembling a theme park. Exactly right for a late afternoon.
12:00 PM📍 See location
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Evening
🍽️ Dinner5:00 PM
Sundowners Restaurant — Sunset Dinner
On the bayside of Key Largo, Sundowners commands the best Florida Bay view of any restaurant in the Upper Keys. The menu leans into fresh local fish — yellowtail, mahi, grouper — and the sunset over the backcountry is reliable and spectacular. Arrive 30 minutes before sunset to get a waterfront table.
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🛏️
Key Largo Bay Marriott Beach Resort
A full-service waterfront resort on Florida Bay with a private beach, water sports, and sunset views across the backcountry mangrove keys. The most comfortable overnight in Key Largo.
Day 2 — Islamorada, FL
Day 2 — Islamorada, FL
🚗 2 hr driving📍 4 stops
🌅
Morning
🚗
Drive
Key Largo, FL → Robbie's Marina, Islamorada
30 min8:00 AM → 8:30 AM
🍽️ Breakfast8:30 AM
Hungry Tarpon at Robbie's — Breakfast
Breakfast at Robbie's — grits, eggs, conch hash, Key lime pancakes — eaten at an open-air counter over Florida Bay while fishing guides prep their skiffs for the morning tide. This is the Keys as working community rather than tourist destination: real people starting a real workday before the vacation visitors arrive.
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Anne's Beach — Morning Wade
★ 3.9A free public beach through red mangrove marsh on Lower Matecumbe Key — shallow, warm, clear, and uncrowded before 10am. The mangrove boardwalk trail adds bird sightings to the swim. Named for conservation activist Anne Eaton who fought to keep this strip of shoreline public.
9:30 AM📍 See location
🍽️
Lunch
🍽️ Lunch10:30 AM
Morada Bay Beach Cafe — Lunch
Barefoot on Florida Bay at a table in the sand — Caribbean fish tacos, conch ceviche, and a frozen drink with a view of the backcountry. The most relaxed lunch experience in the Upper Keys; take your shoes off at the door (there isn't one) and plan to stay longer than you meant to.
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☀️
Afternoon
Holiday Isle Beach — Afternoon Swim
★ 4.8Holiday Isle on Upper Matecumbe Key has a small public beach area and the legendary Tiki Bar (which claims to have invented the rum runner cocktail in 1971) — an afternoon swim followed by the drink that allegedly started here is the quintessential tourist-but-worth-it Islamorada experience.
12:00 PM📍 See location
🌙
Evening
🚗
Drive
Islamorada, FL → Miami, FL
1 hr 30 min5:00 PM → 6:30 PM
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