It's absurd to try and capture all of Winter Park and Maitland in the space of a couple of pages, or to define it as a "neighborhood" – both are vibrant cities with neighborhoods of their own. So we'll just try to hit some of the new highlights and old favorites of this leafy, genteel region, home to Rollins College, the Park Avenue shopping district, a historic African American enclave, a charming network of canals and lakes, and some world-class museums.
Garp & Fuss
348 N. Park Ave., Winter Park, 407-960-5560, garpandfuss.com
Find it back in Park Avenue's Hidden Garden: excellent pub grub as well as more sophisticated gastropub fare, served up in a woman-owned and operated space.
Enzo's Restaurant on the Lake
1130 S. Highway 17-92, Longwood, 407-834-9872, enzos.com
Beautiful and sophisticated, the lakefront setting is as much of a draw as the culinary excellence of this Longwood spot. They've been in business for 37 years, and just this spring OpenTable ranked Enzo's one of the 100 most romantic restaurants in America.
Teak Neighborhood Grill
901 S. Orlando Ave., Maitland, 407-335-4835, teakorlando.com
This Maitland outpost of the MetroWest original offers an identical menu, so you can gorge on their wide selection of hefty burgers (including such delicacies as the cronut burger with half-pound of meat and maple-pepper bacon, or the "Teak Challenge" – a two-pounder with 27 slices of cheese, 24 slices of bacon) closer to home.
The Glass Knife
276 S. Orlando Ave., Winter Park, 407-500-2253, theglassknife.com
Luxe patisserie offers a gorgeous line of cakes, cookies, doughnuts and specialty pastries to satisfy the sweetest of tooths. Coffee from Onyx Coffee Labs (with whom they have an exclusive partnership) makes a perfect pairing, be it drip, pour-over, nitro cold brew or espresso.
Le Café de France
526 S. Park Ave., Winter Park, 407-647-1869, lecafedefrance.com
Longtime favorite at the mouth of Park Avenue will take you back to Paris (or if you've never been there, show you the way). Escargots, coq au vin and a great wine list make your nuit parfait.
Donut Central and Fuelpresso
495 N. Semoran Blvd., Winter Park, 407-821-3000, facebook.com/ donutcentralandfuelpresso
You'll overlook the funny name as soon as you taste a superlative maple-bacon long john or apple fritter from this stealthy new entrant into Orlando's Doughnut Wars.
501 N. Orlando Ave., Maitland, 407-647-9099; kappyssubs.com
One of the most authentic diners in the area has amazingly low prices in a time-warp setting: Get a Philly cheese steak with sliced sirloin and provolone and a root beer float for less than 10 bucks while marveling at the glass and aluminum capsule surrounding you.
The Rustic Table
212 N. Park Ave., Winter Park, 407-853-4101, rustictable.net
Brunch is every day – not just weekends! – at the Rustic Table (formerly Park Station), where you can savor bottomless mimosas with their brunch or lunch menu until 3 p.m.
1282 N. Orange Ave., Winter Park, 407-951-7931, foxtailcoffee.com
Farmhouse sits next door to the original Foxtail in Winter Park, offering not just overflow seating but a wine bar, cocktails on tap, fresh juice, local pastries, an experimental coffee menu, and "the world's largest coffee siphon bar."
The Alfond Inn
300 E. New England Ave., Winter Park, 407-998-8090, thealfondinn.com
Winter Park's boutique hotel also functions as an art gallery, hosting oft-changing selections from Rollins College's Alfond Collection of Contemporary Art. Catch a cocktail or a cup of tea in the lobby and soak up some culture.
Enzian Theater, 1300 S. Orlando Ave., Maitland, 407-629-1088, enzian.org
With its gorgeous horseshoe-shaped wooden bar, movie-themed cocktails and upscale bar food, Eden Bar is a one-of-a-kind drinking experience. The surrounding foliage makes the bar feel semi-tropical, and the loony Bill Plympton mural keeps you laughing.
Winter Park Scenic Boat Tour
312 E. Morse Blvd., Winter Park, 407-644-4056, scenicboattours.com
Impress your Tinder dates with this 12-mile pontoon boat tour through three lakes and two canals in Winter Park. They've been operating since 1938, so it looks like something is working.
Art and History Museums – Maitland
231 W. Packwood Ave., Maitland, 407-539-2181, artandhistory.org
The cultural complex includes several small museums, but the jewel is the Maitland Art Center (a National Historic Landmark), the former artists' colony founded by André Smith.
The Charles Hosmer Morse Museum of American Art
445 N. Park Ave., Winter Park, 407-645-5311, morsemuseum.org
Not only is it world-renowned for its astounding collection of works by Louis Comfort Tiffany, the Morse has the best and biggest museum shop in town.
Mead Botanical Garden
1300 S. Denning Drive, Winter Park, 407-622-6323, meadgarden.org
A garden oasis with bike paths and a picnic area rife with natural fauna and wildlife. Take a hike near forested wetlands, and if you're quiet enough, hear the hawks and wading birds.