The Ultimate Guide To Winter Park, Florida

Winter Park is like New England in Florida. With brick roads, an old money vibe, and even fireplaces in most houses, Winter Park reminds me of my home town in Massachusetts. Winter Park is truly a hidden gem in Florida. The small town is located just north of Orlando - making for the perfect day trip. This ultimate guide to Winter Park is all about the best things to do and eat in Winter Park, Florida. 

This post is all about your guide to Winter Park. 

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When To Visit Winter Park 

As you probably know, Florida gets super hot in the summer and fall months. The summer and fall is also hurricane season!  So try to avoid Florida in the fall and summer. 

Opt for the winter and spring months when you plan your visit to Winter Park. 

My favorite month in Florida is defiantly March. The weather is perfect in Florida in March. 

Getting Around Winter Park 

Fly into the Orlando airport. Winter Park is about a 30 minute drive from the Orlando airport.

Winter Park is super walkable! If you plan on staying in Winter Park your whole trip than I would recommend ubering from the airport because that is the only transportation you will need because it is so walkable. If you plan on going to Disney or golfing then it may be more cost effective to rent a car. 

Where To Stay In Winter Park

$ Hilton Garden Inn - The Hilton Garden Inn is a great option if you are looking to budget a little bit while in Winter Park. Located in Historic Hannibal Square, the Hilton will have everything you need. 

$$ Park Plaza - The Park Plaza is an adorable hotel located on Park Ave. When I first visited my college I stayed here and it was one of the most unique stays of my life. The you enter the Park Plaza you feel like you have entered a different time period. With keys to enter your room, antiques throughout, and a grand staircase leading up to the rooms, you will feel like you are in the Great Gatsby. 

$$$ Alfond Inn - The Alfond Inn the nicest hotel in Winter Park. Located on New England Ave, The Alfond Inn is a luxury boutique hotel owned by Rollins College. Have a meal with locally sourced produce from the area at Hamilton’s Kitchen at the Alfond Inn. Enjoy the lovely decor and homey feel at the Alfond Inn. 

What To Do In Winter Park

Explore Park Ave

Park Ave is a lovely street full of shops, restaurants, and sidewalk cafes - kind of like Winter Parks downtown area. While Park Ave has classic stores like Lululemon they also have unique shops and boutiques. Some of our favorites are Siegal's, Writer's Block Bookstore, and Rocket Fizz.

Winter Park Scenic Boat Tour

Whenever I think of a boat tour I think that it is going to be a huge effort and take up the whole day. Winter Park Scenic Boat Tour is easy and won't take up your whole day. This boat tour is so interesting, I learned way more than I thought I would, all about the nature, animals, and the huge estates around Lake Virginia. You will take surprising routes on this scenic boat tour through winding waterways that will make you feel like you are in a rainforest. 

Wander Through Central Park

If you want to feel like you are a character in the Truman Show be sure to visit Central Park. Central Park has luscious green grass and impeccable landscaping year round. There are perfect little fountains and hidden garden walkways all throughout Central Park.  Central Park is a great place to read a book or wander around. 

Visit The Winter Park Farmers’ Market

On every Saturday from 7am to 1pm local vendors gather to sell fresh produce, baked goods, crafts and more at the Winter Park Farmers Market.

Coming from New England, I have to say that Florida's farmers markets are superior. The Winter Park one is located in downtown Winter Park and is easily one of the best ones I have ever been to.

Location - 150 N New York Ave, Winter Park, FL 32789

Go Golfing

Go golfing in Winter Park! Central Florida is known for their lovely golf courses so, if you love to golf, take advantage of your time in Winter Park. People drive around in golf carts here. Some notable golf courses in Winter Park are The Winter Park Golf Course and The Winter Park Pines Golf Club. 

Walk Down Random Streets

Winter Park has gorgeous brick roads and New England style homes. I love to run down these streets and admire the moss trees and beautiful homes with a lot of character.  If you have extra time in Winter Park or if you just want to decompress walking down these streets are so peaceful. I love walk around the lakeside neighborhoods.

Visit Hannibal Square

Hannibal Square is a toned down version of the nearby Park Ave. You will find delicious restaurants, gorgeous brick roads, and cute little shops to keep you entertained in Hannibal Square. Hannibal Square is on .4 miles from Park Ave so you could definitely combine the two on your itinerary.

Explore Mead Botanical Gardens

Mead Gardens is a tranquil green space full of trails, butterfly gardens, picnic spots, a small pond, and so many unique plants and animals. It is a lovely place for a walk, picnics, photographers, or nature lovers - I see a lot of bird watchers at Mead.

Where To Eat In Winter Park  

Best Coffee and Breakfast Spots In Winter Park

Barnies - Barnies is located on Park Ave and serves delicious coffee, espresso, and breakfast. Barnies is a lovely place for brunch or a quite coffee break. If you decide to sit at Barnies you will be waited on. Be sure to order one of their amazing lattes and, my favorite, avocado toast. 

Foxtail Coffee - Located on Orange Ave, Foxtail Coffee is a great option for your morning cup of Joe, especially if you need to get some work done. The environment at Foxtail is very relaxing, quiet, and has super cute decor with really interesting wood features all throughout the shop. 

Foresters Coffee - Located on Park Ave, Foresters recently opened and it is delicious! Serving rich coffee from all over the globe you will not be disappointed with Foresters Coffee, especially if you like your coffee strong. While you are sipping on your rocket fuel be sure to checkout the unique, hand-made crafts and art for sale. 

Briarpatch Restaurant - If you are looking for a brunch spot Briarpatch is wonderful. You should definitely try the pancakes they are out of this world good. 

Best Resturants In Winter Park

Orchid Thai - If you love Thai food just as much as I do you will absolutely love Orchid. Located on Park Ave, Orchid is a great place for dinner. This is some of the best Thai food I have ever had. Be sure to try the yellow curry. Orchid is a great option if you do not want to spend a fortune on food but still want a good meal. 

Bosphorous - Another one of my all time favorite restaurants in Winter Park is Bosphorous Turkish Cuisine. You will experience Turkey at Bosphorous with their tasty kabobs, pita bread, hummus, Turkish coffee and more. 

Hunger Street Tacos - Oh my goodness, I love Huger Street Tacos! As a college student in Winter Park I am always looking for good and cheap food and it seriously doesn't get better than Hunger Street Tacos.  My favorite is the chicken tacos. 

Best After Dinner Spots In Winter Park

The Glass Knife - Donuts and cake galore at the glass knife. This place is insanely good and has a lovely atmosphere with delicate features. Try the chocolate cake!

Gelato-Go - This place makes very good gelato that tastes like it is straight out of Italy. You can't go wrong with the flavor, they are all amazing. Gelato-Go also makes very good coffee!

Le Macaron French Pastries - Feeling fancy? Grab some French macarons at Le Macaron. There is an endless amount of flavors here and they are all delicious.  

Winter Park Wrap Up

Winter Park is such a charming little town in central Florida and it cannot be missed on a trip to Orlando. We hope this guide to Winter Park inspires you to take a trip to this lovely town in central Florida. If you are looking for more Florida inspiration checkout or Florida articles.

Happy Travels,

Daisy