Saturday

5) 9 A.M. D.I.Y. Neighborhood Tour

Picket-fenced bungalows, moss-laden trees and brick-paved streets fill the historic residential neighborhoods of Thornton Park and Lake Eola Heights to the east and north, respectively, of downtown Orlando’s Lake Eola. Take a D.I.Y. tour to get a feel for Old Florida life aboard one of the orange bikes in the Juice Bike Share program ($8 an hour). Make your first stop Downtown Credo coffee, a social-impact-oriented shop with four locations around town that sources coffee direct from growers and asks customers to name their price for each cup. Make sure to walk that bike around Lake Eola: Bikers are forbidden from cycling on the sidewalks that ring the shore.

6) 11 A.M. House & Garden

In the 19th century, old-money snowbirds from the north began spending their winters beside the lakes of Central Florida, particularly Winter Park, the Orlando neighbor that feels more like a village than a suburb. They and modern-day successors built mansions lining Lakes Osceola, Maitland and Virginia, which are connected by old logging channels: narrow passages about the width of the 18-seat pontoon boats operated by Scenic Boat Tour. The tour company’s hourlong itinerary ($14) takes in the fine homes and the Spanish-Mediterranean-style campus of Rollins College. The excursion is also a nature tour, especially in the slim canals where guides point out a 150-year-old live oak, among other sights.

7) 1 P.M. Double Feature

One of Winter Park’s affluent part-timers was Charles Hosmer Morse, whose heirs eventually amassed the largest collection of glass works by Louis Comfort Tiffany in the world and made it the anchor of the Charles Hosmer Morse Museum of American Art. In addition to wall-size, garden-themed panels, the museum’s Tiffany collection includes the kaleidoscopic chapel he created for the 1893 World’s Columbian Exposition in Chicago and several rooms from Laurelton Hall, his Long Island estate. For contemporary ballast, cross the leafy Rollins College campus to the Cornell Fine Arts Museum, which mounts shows with pieces that range from old master paintings to modern-day neon.

Mathers Social Gathering is a downtown speakeasy-style bar on the third floor of a 19th-century furniture store. Credit Zack Wittman for The New York Times



8) 4 P.M. Pushing Paper

If you’ve shopped in a hip stationary store recently, chances are you’ve seen the festive and funky designs of Rifle Paper Co. The Winter Park design firm operates an airy boutique in the Hannibal Square neighborhood, where you can pick up everything from cards and journals to wrapping paper and iPhone cases in its signature floral patterns. A few blocks east on Winter Park’s main drag, Park Avenue, independent boutiques include Violet Clover, selling blouses and accessories; and Han Design, with unique jewelry and Turkish rugs. Grab a novel and flop down in a cozy armchair at Writer’s Block Bookstore, where the staff tapes their mini book reviews to the shelves.

9) 6:30 P.M. Progressive Feast

Getting around much of Orlando requires a car, but Winter Park offers a bounty of restaurants within walking distance of each other. Start at the Ravenous Pig, staffed by crack bartenders who whip up cocktails that may include a rum-port-spiced apple Needle in the Hay ($12). Move on to bustling Prato, where the partner and chef Brandon McGlamery serves market-inspired Italian dishes, including house-made pastas ($17) and pizzas ($16) cooked in a wood-fired oven. He also oversees Luma on Park, a romantic spot with an open kitchen and a luscious pineapple curd ($8) on the dessert menu.

10) 9 P.M. After-Dinner Art

The culinary arts and the fine arts meet at the Alfond Inn at Rollins, a few blocks from Park Avenue. Established by Rollins College, the nonprofit inn funnels all proceeds to its scholarship programs. Contemporary art fills the ground floor of the 112-room hotel in a rotating arrangement overseen by the curators of the Cornell Fine Arts Museum. Join the locals for post-dinner drinks in admiring the art or sitting around the courtyard fires beside the bougainvillea hedges.