Escape Like a Local: A Long Weekend in Winter Park

Trey Dyer

Trey Dyer

I often get calls from friends visiting Orlando asking me: “What should we do while we’re here? What is there outside of the theme parks?” While theme parks are a great draw for Central Florida visitors, there is so much more to enjoy. Winter Park is an ideal setting for a weekend getaway. For those looking to soak up the local culture in this unique town (minutes from Downtown Orlando), we suggest the following itinerary:


7 p.m. Check into the Alfond Inn (300 E New England Ave)
Two blocks from Winter Park’s beautiful main street, Park Avenue, the Alfond Inn offers muted elegance in the heart of town. 

The Alfond Inn

8 p.m. Stroll over to Bosphorous Restaurant (108 S Park Ave)
A 5 minute walk from the Alfond Inn, Bosphorous Restaurant serves up the best Turkish and Mediterranean cuisine in Central Florida. On nice evenings, the outdoor seating overlooking the park is perfect for people watching. As for dinner, I suggest you start with the Lavash bread and hummus before diving into my favorite entrée, the braised lamb shank served with rice pilaf. 

The Wine Room in Winter Park

The Wine Room in Winter Park

9:30 p.m. Take a two minute walk down to the Wine Room for some post dinner drinks (270 S Park Ave)
With over 156 selections available through state-of-the-art “Enomatic” wine dispensing machines, the Wine Room encourages you to sample many different wines. Choose from the 1 oz, 2.5 oz or 5 oz pour sizes available.

Not a wine fan? The “Flute” machine offers you a wide variety of champagnes to sample and the bar has plenty of ice-cold craft beer selections. With its festive, tasteful atmosphere and great variety of drink options, the Wine Room provides the perfect after dinner experience before calling it a night. 


The Winter Park Country Club

9 a.m. Enjoy the Winter Park Farmers Market (200 W New England Ave)
From 7:00 a.m. to 1:00 p.m. every Saturday, the Winter Park Farmer’s Market is one of our favorite Saturday morning traditions. Just a five minute walk from the Alfond Inn, the Winter Park Farmer’s Market boasts close to 100 different vendors offering pastries, tamales, vegetables, flowers and much more.  Grab a fresh coffee and light breakfast as you stroll through this scenic market.

11 a.m. Play nine holes on the pitch and putt golf course at the Winter Park Country Club (761 Old England Ave)
The nine hole walking course at the Winter Park Country Club takes golfers through the beautiful neighborhood of downtown Winter Park. Lined with giant oak trees and beautiful old Florida houses, the narrow fairways present a challenge to even the most skilled golfers. With rates starting at only $13.00 on weekends, the Winter Park Country Club is a great way to see the town like a local. 

2 p.m. Grab lunch at the Winter Park Fish Company (761 Orange Ave)
Less than a mile from Park Avenue, Winter Park Fish Company will change the way you think about seafood shacks. With fresh fish delivered daily, this local favorite is sure to satisfy your Florida seafood craving. 

Cioppino Seafood Stew from Winter Park Fish Co.

Cioppino Seafood Stew from Winter Park Fish Co.

3 p.m. Take a standup paddleboard tour through the Winter Park Chain of Lakes
Connected by a series of canals that were formerly used to transport logs in the 1800’s, the Winter Park Chain of Lakes provides history, excitement and natural beauty. Whether you are an expert paddleboarder or it is your first time, the Winter Park Chain of Lakes paddleboard tour is a great way to get out and enjoy this growing sport. 

Venetian Canal Paddleboard Tour on the Winter Park Chain of Lakes

Venetian Canal Paddleboard Tour on the Winter Park Chain of Lakes

7:30 p.m. Treat yourself to dinner at Cask and Larder (565 W Fairbanks Ave)
Calling themselves a “Southern Public House,” Cask and Larder has a “steadfast dedication to artisanal foods with a modern sensibility and an unyielding devotion to creating dishes in harmony with the season.” Their southern style and unique dishes, combined with their expansive wine list, makes for great evening out. 

8:30 p.m. Head to the Cask and Larder bar for cocktails
With a microbrewery in house, creative cocktails and over 50 different bourbons, whiskey and ryes, the Cask and Larder bar room is a local favorite for post-dinner drinks. 

Cask and Larder


A big bass from a recent trip with Josh Hamlin

A big bass from a recent trip with Josh Hamlin

6 a.m. Wake up early for world class Bass Fishing
No trip to Central Florida is complete without a day on the water. Central Florida is regarded as the trophy bass fishing capital of the world, with frequent catches of 10-pound bass.  Enjoy this great pastime by booking a fishing charter with Capt. Josh Hamlin, who has been catching bass in Central Florida’s waterways for over 25 years.

11 a.m. Brunch at the Briar Patch (252 N Park Ave)
After a fun morning catching fish you should have a good appetite. With fluffy waffles, pancakes, French toast, and southern favorites like fried green tomatoes, the Briar Patch is one of my favorite spots for breakfast.

12 p.m. Window shop and enjoy the park on Park Avenue
Explore Central Park and the wonderful shops on Park Avenue. Grab some chocolate covered popcorn from Peterbrooke Chocolatier. If you are a football fan, take a short walk off of Park Ave. to the Porch Bar and Grill or PR’s Taco Palace to catch the NFL game.

7 p.m. Dinner at Luma (290 S Park Ave)
Located in the middle of Park Avenue, Luma dishes up American classics with a modern and distinct flare. Named by USA TODAY as the number one foodie spot in Orlando, Luma’s modern kitchen is a local gem you don’t want to miss.


Rollins College in Winter Park

Rollins College in Winter Park

9 a.m. Grab Breakfast at Keke’s (345 W Fairbanks Ave)
Start your morning with an omelet or stuffed French toast just a couple blocks away from the Alfond Inn.

10:30 a.m. Take a historic tour of Rollins College (1000 Holt Ave)
The first college in Florida, this 70-acre campus is filled with gorgeous Spanish-Mediterranean architecture and art. Sitting on the shores of Lake Virginia, Rollins College Campus Tours are a great way to delve into the history and beauty of Central Florida. 

1 p.m. Eat lunch at Tibby’s New Orleans Kitchen (2203 Aloma Ave)
Cajun food in Central Florida does not get better than Tibby’s. From their Shrimp and Grits to hefty Po Boy Sandwiches, Tibby’s brings the taste of Bourbon Street to Winter Park.

2 p.m. Congratulate yourself on a weekend well spent and head on home

Winter Park is a historic and unique area of Central Florida with a lot to offer. If you’re looking for other great things to do in town, be sure to check out our booking and recommendation site, Get Local, to soak up our favorite local experiences.