Orlando
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Weekend Getaways

Orlando

27 itineraries · Day trips, weekends & long weekends
27 hand-curated itineraries from Orlando — active, relaxed, cultural — all within a few hours' drive. Think Ocala Springs — Juniper Springs Paddle & the Alexander Springs Timucuan Trail, or New Smyrna Beach — Flagler Avenue, the Lagoon & Canal Street Arts. Real places, real drives, no filler.
🥾 Active
Wekiwa Springs — Crystal Spring Swim, Wekiva River Paddle & Rock Springs Run Trails
Barely half an hour north of downtown Orlando, Wekiwa Springs State Park protects one of Central Florida's great spring systems — a sapphire boil of 72-degree water welling up from the aquifer and gathering into the tea-dark Wekiva River, a federally designated Wild and Scenic waterway. This is an active day built around the water: a morning swim in the spring pool, a paddle down the cypress-lined Wekiva River and its tributary Rock Springs Run, and afternoon hiking on the sandhill and hammock trails that thread the park's 7,000 acres of longleaf pine, scrub, and swamp. Wildlife is everywhere — white-tailed deer and gopher tortoises on the uplands, turtles and wading birds along the river, and, more often than not, an alligator sunning on a distant bank. It is the quintessential Central Florida wild day, close enough to reach before the parking fills yet a world apart from the theme parks.
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Wekiva SpringsDay trip
🌿 Relaxed
Clermont — Lakeridge Wine, the Citrus Tower & the Chain of Lakes
Just forty minutes west of Orlando's theme-park sprawl, Clermont trades roller coasters for rolling citrus hills, spring-fed lakes, and Florida's largest winery. This unhurried day pairs a morning wine tasting and vineyard tour at Lakeridge Winery — the oldest and largest producer in the state — with a climb up the mid-century Citrus Tower for a green-and-blue panorama across the Clermont chain of lakes. Afternoon slides down to the Lake Minneola waterfront and the working groves and animal barns of the Showcase of Citrus, where you can ride a monster-truck grove tour and squeeze fresh juice. It is a slow, sensory day of wine, fruit, and water that feels a world away from the parks, yet is close enough to be home before dark.
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Lake County Wine — ClermontDay trip
🏛️ Cultural
Winter Park — Tiffany Glass, Brick Avenues & the Chain of Lakes
Just twenty minutes northeast of downtown Orlando, Winter Park is the region's most refined cultural enclave — a lakeside city of cobbled brick streets, live-oak canopies, and a museum holding the world's most comprehensive collection of Tiffany glass. This single day pairs two of Florida's finest small museums with a slow cruise through the historic Chain of Lakes. Morning belongs to the Charles Hosmer Morse Museum of American Art, home to the salvaged chapel interior Louis Comfort Tiffany built for the 1893 World's Columbian Exposition and the rescued windows and lamps from his Long Island estate, Laurelton Hall. Midday moves to leafy Park Avenue for lunch and shopping, followed by the Scenic Boat Tour's pontoon glide through mansion-lined canals, and the afternoon closes at the Rollins College campus and its Cornell Fine Arts Museum on the shore of Lake Virginia.
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Winter ParkDay trip