27 hand-curated itineraries from Miami — active, relaxed, cultural — all within a few hours' drive. Think Two Days in the River of Grass, or Upper Keys Slow Escape: Sunsets, Snorkeling & No Agenda. Real places, real drives, no filler.
🥾 Active
Day trip
River of Grass: Everglades by Foot, Canoe & Boat
An hour southwest of Miami, one of the most biologically extraordinary places on Earth begins at a parking lot. The Everglades is not a swamp — it is a slow, shallow river of grass 60 miles wide and 100 miles long, creeping southward from Lake Okeechobee to Florida Bay. Walk boardwalks where alligators sun themselves within arm's reach, canoe through mangrove tunnels older than the country, and reach the remote outpost of Flamingo where the only place in the world where alligators and crocodiles coexist in the wild greets you with indifference.
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Everglades National ParkDay trip
Snorkel the First Undersea Park in America
Day trip
Cypress Swamps & Panther Trails
Day trip
Two Days in the River of Grass
Weekend
Keys Active: Reef Diving, Flats Fishing & a Sunken Island
Weekend
Mangroves, Wetlands & Turquoise Waters
Weekend
Wild Florida: Everglades, Big Cypress & Ancient Swamp Forest
Long weekend
Keys Active Road Trip: Reef, Flats & Bahia Honda's Best Beach
Long weekend
Wetlands, Mangroves & Coastal Trails
Long weekend
🌿 Relaxed
Day trip
Islamorada Slow: Tarpon, Tacos & a Keys Sunset
An hour and a half south of Miami, Islamorada is the Keys at their most authentically laid-back — not the tourist circus of Key West but a real community of fishing guides, marine biologists, and longtime Keys residents who have organized their lives around the water. Wade in the shallows at Anne's Beach, hand-feed 150-pound tarpon from Robbie's dock, eat conch fritters at a 1947 restaurant, and watch the sun drop behind Florida Bay with a cold beer in hand. This is the trip for people who want the Keys without the crowds.
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Florida Keys — IslamoradaDay trip
Atlantic Avenue: The Gold Coast's Best Small-City Day
Day trip
Leafy Sanctuaries & Coastal Tranquility
Day trip
Upper Keys Slow Escape: Sunsets, Snorkeling & No Agenda
Weekend
Gold Coast Drift: Palm Beach Luxury & Delray's Village Charm
Weekend
Everglades, Corkscrew Swamp & the Naples Gulf Coast
Weekend
Keys to Key West: Three Days Down the Overseas Highway
Long weekend
Treasure Coast Drift: River Towns, Botanical Gardens & Bok Tower
Long weekend
Florida Keys Scenic Drive: Hammock, Beach & Tarpon
Long weekend
🏛️ Cultural
Day trip
Gilded Age Grandeur on the Gold Coast
Drive north along Florida's Gold Coast to Palm Beach, where Standard Oil co-founder Henry Flagler built a winter empire that opened South Florida to the world. Explore his 55-room Gilded Age mansion turned museum, the Southeast's finest art collection at the Norton, and Worth Avenue's Mediterranean Revival boutiques before heading home along the Intracoastal.
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Palm Beach CountyDay trip
Addison Mizner's Coral Gables & the Biltmore
Day trip
Timeless Stories & Cultural Treasures
Day trip
Palm Beach Mansions & Morikami's Japanese Gardens
Weekend
Keys History: Humphrey Bogart's Boat & the Deep's Museum
Weekend
Palm Beach: Gilded Age Mansions, Mizner Architecture & Worth Avenue
Weekend
Gold Coast to Bok Tower: Three Days of Florida's Past
Long weekend
Florida Keys Cultural Road Trip: Reefs, Ruins & Hardwood Hammocks
Long weekend
Florida Keys: Hemingway, Truman & the History Beneath the Water
Long weekend