Mikaela J

A Weekend in Winter Park, Florida {Travel Guide}

Every time I tell someone I live near Orlando I get the “Oh! So so you must go to Disney all the time” response.  As much as I love Disney and my kids would spend every waking minute there, I adore my home in Winter Park, Florida. If you are not familiar with Winter Park, it is a small, quiet city just outside of Orlando that boasts beautiful gardens, lush greenery and quaint boutiques and restaurants filled with charm and character.

If you are lucky enough to vacation in Winter Park, or if you are just looking for a change of pace during your Disney vacation, check out these amazing things to do while you are here!

Winter Park, Florida City Guide

Where to Stay in Winter Park, Florida

The Alfond Inn is especially important to me because I went to college in Winter Park and this hotel provides scholarships for students to attend Rollins College.  The hotel is absolutely stunning.  It is a boutique-style hotel filled with gallery-quality artwork, an award-winning restaurant and the most comfortable beds.  The hotel is also walking distance to most of the bars, restaurants and shopping in the area so it is extremely convenient! And while you are there, don’t forget to sip the “Park Ave Pearl” while sitting out by the pool or cozied up on a rocking chair by the fire pit.

Alfond Inn Rollins College

Where to Eat in Winter Park, Florida

Briarpatch is the cutest cafe located on Park Avenue overlooking Central Park.  In addition to the most delicious pancakes I have ever tasted, they are also known for their prosecco white peach bellinis, creamy cheese grits and house-made layer cakes. They do not take reservations and they are only open for breakfast and lunch, but even if you have to wait in line, you will not be disappointed.

Prato is definitely a favorite for locals and visitors alike.  The delicious Italian dishes are created with fresh, seasonal ingredients and their homemade pasta and wood-fired pizzas will leave you wanting more.  The rustic vibe is perfect for a date night out or a family-friendly meal.  Their menu changes seasonally, but don’t leave without trying their Meatballs,  Escarole Caesar Salad and Diavolo Pizza.  The pasta dishes can also be ordered in half portions so it is a great way to try a variety of things!

Bosphorous Turkish Cuisine is another local favorite and when walking by, you will often see the tables packed with diners snacking on their famous Lavas hollow bread.  The food is always delicious and packed with flavor and most of their dishes are made with items shipped directly from Turkey!

One of my favorite date-night spots in Winter Park is Luma on Park.  It is in the same restaurant group as Prato and the food is always delicious and unique.  They have a great bar area, the service is fantastic and the wine list is extensive.  They also have outdoor tables and on a nice evening, it can be the perfect place to people-watch over a delicious meal.  If you are looking for a special evening out, definitely call early and book the chef’s table.  It is an experience not to be missed!  Luma was also just awarded the AAA Four Diamond Restaurant Award, so it is definitely worth a visit!

A recent addition to Park Avenue, Sushi Pop, is a contemporary seafood and sushi restaurant unlike anything I have ever tried.  The menu is perfectly curated with the freshest and most delicious flavors.  The cocktails are well thought out and the vibe is modern, yet relaxed.  Don’t leave without trying the Low Rider and the Royal Treatment.

If you are staying at The Alfond Inn, The Ravenous Pig is a little too far to walk, but it is well worth the quick uber trip.  A James Beard nominee and recognized by the New York Times, The Ravenous Pig serves up southern-style dishes using the freshest local ingredients.  The restaurant even houses its own small-batch craft brewery featuring year-round favorites and limited edition runs. The Ravenous Pub Burger is awesome and you can’t miss the Pig Tails dessert.

What to Do in Winter Park, Florida

If your visit falls over a weekend, the Winter Park Farmer’s Market is the perfect Saturday activity. Located in the old train depot, the Farmer’s Market is a small collection of vendors from around the area.  You can find delicious food, fresh-pressed juice and a beautiful selection of plants and flowers. Just don’t leave without grabbing a bag (or two) of the kettle corn!

The Winter Park Scenic Boat Tour is one of my all-time favorite things to do for guests visiting Winter Park.  The tour is an awesome way to relax and see some of the beautiful lakefront homes in the city.  The hour-long pontoon boat tour features an off-the-beaten-path vacation experience right in the heart of Winter Park.  The tour guides are great and they share so much history about the city.  You are often able to see beautiful plants, unique birds and gorgeous homes.  If you are traveling with a large party, you can even rent a private boat and bring your own cocktails and snacks to enjoy during the tour.

Winter Park Boat Tour

Rollins College is a beautiful liberal arts college right in the heart of Winter Park.  It has been voted Princeton Review’s Most Beautiful College Campus and it has tons of charm, character and history.  The campus is situated directly on Lake Virginia and even has a beautifully curated art museum on-site that is free to the public. It would definitely be worth your time to take a walk around campus to check out the beautiful buildings and lake-front view. 

If you and your crew are looking for something with a bit more of a kick, Hop On  Beer Tours is an awesome change of pace.  A bus will shuttle you and your friends around to some of the local breweries where you can enjoy local beer, awesome food and great company.  If you end up at The Bear & Peacock, make sure to grab the party games from behind the bar to up the good time!

Finally, one of the things that makes Winter Park so special is the “downtown” area located on and around Park Avenue.  The quaint streets are filled with adorable restaurants and local boutiques. Sit outside and enjoy a glass of wine, sip a cup of coffee, or pick up a piece of local art. There are so many cute stores to explore!

I hope this travel guide to Winter Park, Florida helps you plan your trip or inspires you to come visit! Always feel free to reach out with any questions and happy traveling!