Winter Park, FL: What To Do & See

Winter Park, FL: What To Do & See

About a month ago, my boyfriend and I decided we wanted to take a last minute trip to Orlando. As theme park fanatics, we of course wanted to visit Disney World and Universal Studios, but we also wanted to start the trip by taking a few relaxing days to ourselves. After a little bit of research, I discovered Winter Park, a city in Florida just north of Orlando. Once I laid eyes on The Alfond Inn, I knew we had to visit the charming city immediately.

Where To Stay


When we arrived at The Alfond Inn, I knew instantly that we were going to have an enjoyable stay. In one word, the hotel is stunning. When driving up to the main entrance, it was just just so eye-catching and inviting, and that was even before we saw how beautiful the interiror is. The hotel is actually owned by Rollins College, which is located up the street, and when they created the hotel they decided to make it an extension of a fine arts museum. Throughout our stay we were immersed in the world of art, and surrounded by dozens of stunning pieces.

winter park travel, winter park vacation, orlando travel, winter park alfond inn, alfond inn review

Our room was beyond beautiful. We stayed in a king room, and we spent most of our time on our room’s balcony overlooking the city around us. I think the balcony was Matt’s favorite part of the resort. He would just sit there drinking his coffee and I’ve never seen him more at peace.

winter park travel, winter park vacation, orlando travel, winter park alfond inn, alfond inn review


After settling in, Matt and I decided to explore Winter Park. Upon leaving the hotel, we were immediately greeted by brick roads and stunning architecture. Within a few minutes of walking, we found ourselves on Park Avenue, Winter Park’s main street. Park Avenue is home to dozens of incredible shops and restaurants. I felt right at home. And by home, I mean a much, much nicer version of my actual home. We spent most of our time in Winter Park shopping, trying new restaurants, and lounging by the beautiful rooftop pool at The Alfond Inn.

Where To Eat

winter park travel, winter park vacation, orlando travel, winter park alfond inn, alfond inn review
Hamilton’s Kitchen
Since we were staying at The Alfond Inn, we were lucky enough to be under the same roof as Hamilton’s Kitchen. The first meal we had in Winter Park was at the hotel’s restaurant, and it set the bar pretty high for the remainder of our trip. I had the fish tacos and Matt ordered the Steak Frites. They were both absolutely delicious, but the real gem were the truffle fries. Fun fact: french fries are actually my favorite food, and truffle fries take my love to a whole new level. In fact, we loved them so much, that the very next day we decided to have room service, and ordered a huge plate of them. I was sad to leave The Alfond Inn for MANY reasons, but I would be lying if I said truffle fries weren’t pretty high on that list.


The Coop
Living in the Northeast, Matt and I don’t get to indulge in southern cooking often, so when The Coop was recommended to us, we basically ran there the first day of our trip. The food was delicious and the definition of southern comfort food, and we left beyond full. Matt and I both ordered the Chicken N’Dumplings. Perfect choice.

Cocina 214
After eating the fish tacos at Hamilton’s Kitchen our first day in Winter Park, I was craving some mexican food! Cocina 214 is a contemporary Mexican and Tex-Mex kitchen. I’ve had quite a few tacos in my lifetime, but the steak tacos at Cocina 214 were unbelievable. I ate so many chips and guacamole, that the waiter (in the most polite way possible) said he wasn’t going to fill our chip bowl again.

Barnie’s Coffee Kitchen
I have only recently become a coffee drinker, and I’m not going to lie, I’m a bit particular. I only like iced coffee, and I am absolutely partial to the iced coffee at my local bagel shop. Despite my picky ways, Matt and I decided to try Barnie’s Coffee Kitchen one morning. I am not lying, it was one of the best cups of coffee I have ever had. I was actually disappointed that we didn’t have time the day we were leaving to grab another cup. The shop was also ultra cool and trendy, with marble tables both inside and outside.

What To Do

Go Swimming | Florida is basically always hot, but the week we were visiting, it was especially warm. The warm weather mixed with the fact that Matt hasn’t had a day off of work in almost a year, meant we wanted to do a bit of relaxing while we were in Winter Park. The Alfond Inn has an INCREDIBLE rooftop pool that we spent quite a bit of time at. It was like an oasis.

winter park travel, winter park vacation, orlando travel, winter park alfond inn, alfond inn review


Exploring & Shopping | Honestly, the town of Winter Park was so beautiful, we spent a ton of time just exploring. Since the city is so pedestrian-friendly we would spend hours just walking. We would look at all of the beautiful houses, shop in all of the stores, and just enjoy the peacefulness and beauty around us. Let’s just say we spent a ton of time in the Park Avenue Shopping District!


Visit the Museums | Winter Park is home to so many incredible museums. While we didn’t have time to visit any (besides the museum in our hotel), we wish we had.

Winter Park Scenic Boat Tour | While we didn’t get to go on a tour while we were in Winter Park, it was highly recommended by the locals. It’s first on our list next time we visit.

winter park, winter park florida, winter park vacation


We had such a wonderful time in Winter Park. Our only complaint is that we didn’t have more time there. Next time we visit Winter Park, we will definitely extend our stay.

Have you ever been to Winter Park, Florida?

A huge thank you to The Alfond Inn for sponsoring our stay. Thank you for making our trip so memorable.

  • Kara

    I’ve never been to Winter Park but it sounds lovely! The hotel looks amazing as well.

  • That hotel! I would have swooned on the spot. What a lovely place to stay!

  • Amanda Love

    The hotel alone is enough to entice you. I can stay there and not go out, just relax and sleep all day! But it’s also important to tour around especially if the place is as lovely as this! Thanks for the guide!

  • Kimberly Stroh

    I LOVE Winter Park! It’s a hidden gem that many don’t know about. The shopping is excellent too!

  • Kim Byars Croisant

    What a quaint and quite stunning place to visit. I’d go there in a heart beat for vacation. Anywhere in Florida please!!! I love your bathing suit!!

  • CourtneyLynne Storms

    I lived in Orlando for 8+ years and loved taking day trips to winter park. So many fabulous shops and restarants

  • This looks like such a fun vacation! The Inn is absolutely gorgeous! I would love to visit during the winter when it gets so stinking cold here in Idaho!

  • Cynthia @craftoflaughter

    The town looks like such a perfect place for a stay! The food alone sold me! Love your outfits too

  • Truffle fries are really, really good – I love ordering them when offered. The interior of the Alfond Inn is beautiful.

  • Mandy Young Carter

    Living in Orlando for few years, I have been to Winter Park and I agree it is an awesome area. Those fries look so delicious.

  • A lovely place and great photos here, I am in need of a weekend getaway right now.