About 15 minutes Northeast of the high-rise buildings on the Downtown Orlando skyline is the charming town of Winter Park. It’s full of elegant oak trees and red brick streets. Winter Park feels like a genuine piece of colonial history and charm, hidden amidst masses of cookie-cutter Florida suburbs.

Park Avenue
Take a stroll down Park Avenue. Inhale the rose gardens which are blooming most of the year. (Perk of Florida weather!) Bring a blanket to lay out, and enjoy the breeze in the beautiful oak trees and calm fountains. It’s the perfect spot to sip a latte, read a book, and love the outdoors.

Park Avenue also has an abundance of French and other European sidewalk cafes and shops. So if you’re hungry, grab a bite and people watch for a while. It has a relaxing, vibe and is surprisingly not overrun by students from Rollins–the local private college.

Park Avenue Consignment
There is also a consignment shop on Park Avenue called Cida. Since Winter Park has old money, there are ridiculously priced items (furs for $2,000). But there are also fantastic deals on their clearance for $5-$10. It’s hit-or-miss, but you might score some awesome vintage or Antho items for great prices.

Kayaking on the lakes of Winter Park, FL

Kayaking on the Waterways
If you’re feeling adventurous, there are kayaking tours that take you on the lakes or Winter Park. These take you through the various waterways and even to Dog Island. Kayaking makes for a fun afternoon, but it can take about 4 hours. So pack a lunch, some wine, and maybe a jacket. Bring a flashlight if you’ll be out after dark. The waterways can be a little spooky to navigate when the sun goes down. This is a beautiful experience and a great way to see natural Florida.

Kayaking in Winter Park FL

Scenic Boat Tour
If you’re in a less athletic mood, the Scenic Boat Tour of Winter Park is also lovely, and it will show you the largest mansions and give you a delightful historic tour of the lakes and history of the area. The entrance is on Morse Ave, right of Park Ave.

Delicious Eats
Winter Park has so many wonderful restaurants. If you’re there briefly, these are the ones you can NOT miss:

•  Ravenous Pig
  The best, most perfectly balanced, beautiful food you’ll find…possibly in the whole city. Amazing for lunch or dinner. Make reservations if going with a large group. (There are some seats available for walk-ins, but you might wait a while with a large group.) The Duval cocktail is not to be missed.

•  Dylan’s Deli
  This French guy makes one soup a day, and that soup is always perfect. His sandwiches are to die for. Perfect for lunch. Call first though, as he shuts down some days.

• Cask and Larder
  I recommend this for Sunday brunch. And you’ve got to get the chicken and waffles. It’s the most perfect imaginable breakfast. These guys know what they’re doing. An immaculately cooked waffle, perfectly juicy fried chicken, a small plot of sheep ricotta (never heard of that before this place), and 8 perfect blackberries. It’s not cheap, but it’s memorable. Do it. You’ll have no regrets. It’s Southern food at its gourmet best.

• 

  Fruit tarts at Croissant Gourmet — Winter Park, FL

  Croissant Gourmet
  On Park Avenue and Morse, this place has the most beautiful little French fruit tastes and croissants. Grab a breakfast snack here and eat it in the park while you read a paper.

My father is an antiques and salvage dealer, and for years he’s done salvage on Winter Park homes. Before they throw a wrecking ball through homes built in the 1920s and 30s, my dad is the last one to buzz through, toss cash at the owner, and gut the place into a U-haul. He always finds interesting antique furnishing, and the occasional rare book. (If you ever need to buy antique housing materials, I can pass you his number.)  I’ve been exploring the nooks and crannies of Winter Park for 15 years, and it’s one of my favorite places to enjoy an afternoon.