One Christmas, my family decided to get away, so we flew down south and spent the entire holiday week in Florida, driving up the coast and waking up to sunny, clear skies and dolphins in the ocean — much different from the snowy-white wonderland I’m used to as a Canadian. The traditional clementines we usually received in our stockings were replaced by (much more superior) fresh oranges that we plucked off the trees in the backyard. My memories of the trip and visiting Orlando are fond ones to say the least, but in the last decade, the city has changed and grown up from its reputation of just being home to fields of orange groves. Its downtown neighborhoods have maintained their tight-knit communities, and the greater Orlando spreads far and wide, boasting a bounty of lakes and oak trees. For photographer Jessica Bennett, it’s the people and culture that have kept her in love with the city for over 30 years — and her family for over 3 generations! When she’s not traveling, Jessica and her husband enjoy Orlando’s offering of great food, better coffee, and gabbing with the locals. Today, Jessica is sharing her ideal 24 hours in the bright and sunny city of Orlando! —Sabrina
8 am: Start off your morning at East End Market. Grab a coffee from Lineage Coffee Roaster and a croissant from Olde Hearth Bread Company. Relax in the garden surrounded by all the pretty plants by Porch Therapy 99 Market, and don’t forget to grab some goodies to take home for later.
9 am: Down the street, nestled in Audubon Park District, is Palmers Garden and Goods. Take a walk through their garden and pick up plants to fill your own beautiful landscapes at home.
9:30 am: Time for a little shopping! Lake Ivanhoe Row has something for everyone. Visit Cloak & Dapper for the perfect gift for him, among some of the best furniture and antique shops in the area, such as 1618 Something Different and Washburn Imports.
11 am: If you are anything like me, you are ready for round two of coffee. Propagation is the perfect mid-morning coffee hang. Filled with refinished mid-century pieces and small goods for sale, you get the best of both worlds.
Noon: The Strand is one of my favorite lunch spots in town, with locally sourced ingredients and a constantly changing menu. You will always have a great experience. If you want to go for dinner, make sure to get a pretzel served with their house-made pimento cheese.
1:30 pm: P is for Pie, and pie is the perfect after-lunch dessert. From mini pies, to pie pops and — my favorite — the oatmeal pie, you will want to try them all. Also serving Stumptown cold brew, perfect for those hot Florida afternoons.
2 pm: Drive over to Winter Park and enjoy an afternoon picnic with your recent pie purchase in Central Park. Walk the shops along Park Avenue and find so many great boutiques, like Violet Clover and The Impeccable Pig.
3:30 pm: Walk a few blocks down New England Avenue to Hannibal Square for a refreshing pressed juice from Extract, grab your favorite stationery goods at Rifle Paper Co., and personal care products next door at Pure Blends.
5 pm: Happy hour at Cask & Larder, where the house-brewed beers are half off and a great selection of appetizers are offered. C&L is a modern take on southern cuisine with an on-site brewery and extensive cocktail list. The bar opens for happy hour from 4 pm to 6 pm and dinner every day. If you are around on Sunday, the brunch menu is incredible. I mean, who doesn’t love Nashville hot chicken and waffles? Yum!
7 pm: Dinner at Prato. Grab a delicious cocktail and an order of their famous meatballs. We love so many items on the menu, the best thing to do is order lots to share — from stone-fired pizzas to handcrafted pastas, there is something for everyone. Try my favorite, the Fiorentina pizza.