Day Trips from Orlando: Mount Dora, Winter Garden and Sanford

The best Orlando vacations include leaving Orlando. Within an hour’s drive — less, in two cases — sit three small towns that deliver everything the resort corridor can’t: brick streets, independent shops, lakefront sunsets and main streets that belong to the people who live on them. Mount Dora, Winter Garden and Sanford are the holy trinity of Central Florida day trips. Here’s how to do each one right.

Winter Garden: The Closest Thing to a Perfect Saturday

Drive time: about 25 minutes west

Winter Garden is the day trip you can do on a whim, and its Plant Street is the model every Florida main street wants to be. The historic downtown runs along a brick-paved strip shaded by oaks, with the 22-mile West Orange Trail threading straight through it — rent a bike and the town becomes a trail town.

Anchor the day at Plant Street Market, the indoor food hall where Crooked Can Brewing pours its own lagers beside a dozen local food vendors. Saturday mornings bring one of the region’s biggest farmers markets to the downtown pavilion. The restored Garden Theatre keeps a real events calendar, the splash pad keeps kids busy, and the whole operation runs at a pace that feels like 1955 in the best way. Winter Garden was even named an official “Hallmark Christmas Town” — visit in December and you’ll get it instantly.

Don’t miss: a bike ride on the West Orange Trail, a Crooked Can West Orange Trailblazer lager at the market, and the Saturday farmers market if your timing lines up.

Mount Dora: Antiques, Lakes and Old Florida Charm

Drive time: about 40 minutes northwest

Perched on the shore of Lake Dora — actually on a hill, by Florida standards — Mount Dora is the state’s festival-and-antiques capital, a town of 19th-century bones and serious browsing. The walkable downtown along Donnelly Street and its side avenues packs boutiques, galleries, jewelers and cafés into a few storybook blocks, with the lake glittering at the bottom of the hill.

Serious pickers plan around Renninger’s, the sprawling antiques and flea market just outside town, which hosts enormous Extravaganza weekends several times a year. October brings the Mount Dora Craft Fair, which takes over the entire downtown. And down at the waterfront, look for the Mount Dora lighthouse — famously the only inland freshwater lighthouse in Florida.

Mount Dora rewards slowness: a boat tour on the lake, ice cream on Donnelly, an hour lost in a vintage mall. It’s the furthest of the three and the one that feels most like a true getaway.

Don’t miss: sunset over Lake Dora from the waterfront, Renninger’s on an Extravaganza weekend, and the craft fair every October.

Sanford: The Gritty, Delicious Dark Horse

Drive time: about 35 minutes northeast (or ride SunRail)

Sanford is the pick for people who find the other two a little too cute. Its historic downtown runs along brick-lined First Street to the Lake Monroe waterfront — a working, lived-in main street of antique shops, folk-art galleries, an indie bookstore and the famous four-sided clock tower standing over it all.

What sets Sanford apart is appetite. This is one of Florida’s great little food-and-drink towns: a German beer hall tradition anchored by Hollerbach’s, a craft beer scene that punches far above the town’s weight, cocktail bars, and restaurants that draw Orlandoans north on purpose. The waterfront marina and riverwalk give it a breezy finish, and the SunRail station makes it the one day trip you can do without a car.

Don’t miss: an evening on First Street when the restaurants and taprooms are all lit up, the Saturday market energy downtown, and sunset on the Lake Monroe riverwalk.

How to Choose

• Shortest drive, fullest day: Winter Garden — market, trail, market hall, done by dinner.
• Browsing and romance: Mount Dora — antiques, lake views, festival weekends.
• Food, beer and edge: Sanford — come hungry, stay late.
• No car: Sanford by SunRail, Winter Park (an honorary fourth) by train or a short drive.

However you choose, the formula is the same: leave after breakfast, be home by dark, and wonder why you don’t do it every weekend. Every Orlando local eventually learns this geography. Now it’s yours.