‘The Winters’ – Florida’s millionaires playground! 🇺🇸

Part of my Real Florida Guide

If you’ve had your fill of theme parks and souvenir shops, take a drive outside of Orlando and hang with the rich and famous!

Winter Park

If you’re in the Orlando area with a car, find yourself growing tired of the tourist trap and fancy seeing ‘how the other half live’ – then look no further than Winter Park!

Around 20 – 30 minutes north of Disney, Winter Park is that welcomed break you have been seeking, away from the hustle, the bustle and the mouse ears.

Tip: Before you set off, put ‘Park Avenue’ into your sat nav (or use phone maps if your car company has unhelpfully disabled the nav) as this is the heart of Winter Park and the best place to park up.

Like most places in central Florida, the majority of parking is free and there’s plenty of it. This, we like!

Park Avenue – a little like its New York namesake – is a an upscale boutique shopping district, complete with classy restaurants, cafe culture and all manner of independent stores.

If you’re after posh dentistry, presents for the pooch or a fine wine, then yes, this is where you’ll find all of that! You can also sit down and have your shoes polished in the street or jump aboard a bicycle made for two – and why not?

As well a the obvious wealth, Winter Park has the type of old-fashioned, genuine charm that you simply don’t get in the tourist areas of Florida.

Winter Park has plenty of greenery too, with lush parks and palm tree-lined neighbourhoods to explore on foot. Lots of wildlife too – especially squirrels.

The Scenic Boat Tour

But if Winter Park is most famous for anything, it’s the ‘Scenic Boat Tour’. Believe it or not, this is the longest serving attraction in the entire state of Florida, having established itself way back in 1938!

The Scenic Boat Tour can be found at the East end of Morse Avenue – less than a 10 minute walk from Park Ave. There are signs will guide you easily.

For just 16 bucks (2022 price), you can take an hour long guided cruise through 12 miles of tranquil lake. Trust me, on the hottest of Florida days, you simply can’t beat the breeze from the water! Remember to put on your sun cream!

Not only will you catch a glimpse of sweeping cypress trees, herons, sea snakes, paddle-boarders and water skiers, but the tour also takes you past the millionaire mansions that overlook the lakes. Pure lottery win material!

For those wanting to see how the rich kids get educated, then look out for Rollins College along the way. This prestigious school comes complete with its own private beach and tennis courts.

Head over to my Instagram @SunSeeandSuitcase to watch a short video of the boat trip!

If shopping, eating, drinking and boating is not your thing, however, Winter Park also has soccer and softball fields, should you wish to go and watch a game or perhaps partake yourself. There’s also a fancy golf course and a Tiffany Morse Museum for art and antique lovers.

If you’re not with your own wheels, then there’s a SunRail station that will get you into Winter Park and out to almost anywhere in Florida. If you’re feeling really adventurous, you can also pick up an Amtrak train from the station and venture further afield. Amtrak serves more than 500 destinations in 46 states; you can even take a ‘ski-train’ to Denver, should the fancy take you – and you have time on your side.

Winter Garden

Like Winter Park, Winter Garden is a cute little town brimming with boutique stores, quaint eateries and a sense of sophistication.

Winter Garden is also just a 20 – 30 minute car drive from Orlando (albeit in the opposite direction to Winter Park) and provides an equally peaceful escape from the hustle and bustle of the theme parks. It’s also relatively close to the Apopka Wildlife Drive, if you find yourself up that way.

The Winter Garden Farmers Market is held every Saturday between 08:00 and 13:00 and is super-popular, so if you are visiting during this time you may notice parking is a little busier.

Take a little look at Winter Garden in my vid.