Our Train Adventure to Historic Downtown Winter Park

It started off simple enough – I made a dinner reservation at a great steakhouse for Valentine’s Day, thinking my beautiful wife, Tiffany, and I would enjoy a nice evening out with a fantastic meal, a couple of drinks, and a chance to slow down and enjoy each other’s company. But as we started talking about it, one idea led to another, and before we knew it, our plans had grown into something much bigger.

We decided to make a whole day of it, taking the train to historic Winter Park instead of driving, which, let’s be honest, made the trip feel more like an adventure than just a dinner date. Tiffany booked the train tickets, and together we picked out a boutique hotel that was not only right near the train stop but also close enough to our dinner reservation for a quick Uber ride – practically made for the kind of effortless, no-stress evening we had in mind. Now, instead of just going out for a nice meal, we’d be spending the day wandering through the shops, taking in the charm of Park Avenue, and turning Valentine’s Day into something even more special.

Our overnight adventure was set to begin with a simple plan – head out around 1 p.m., drive to DeLand, and catch the Amtrak for a quick 45-minute ride to Winter Park. From there, the journey would unfold. But as travel often reminds us, plans are just a suggestion.

A winter storm up in New York had other ideas, delaying our train and throwing a bit of uncertainty into the mix. Just as we started wondering how this would shake up our schedule, Amtrak called with an unexpected twist… an earlier train was leaving at 9:40 a.m.! Luckily, Tiffany had wisely packed the night before, so we were ready to go fast. A change of plans, yes, but not a setback. If anything, it added a little extra spark to the start of our adventure. After all, the best trips always come with a few surprises!

We boarded the train, eager for our trip, but quickly realized that many other passengers had also been rerouted to this earlier train. It was a bit tricky finding open seats. Eventually, we were ushered into the lounge car, where drinks were served. To our surprise, the two conductors, Tobias and Randy (pictured above), sat down near us. We struck up a conversation, asking about their experiences on the job. I told them about my writing for ECC and how I was working on an article about our trip. Tobias, who was so generous, offered us a personal tour of the train. He showed us the sleeper cars, dining cars, and even the luggage compartments – an unexpected and fascinating peek into the workings of Amtrak. It was truly an unforgettable ride, and before we knew it, we had arrived at our destination.

Exploring Historic Downtown Winter Park

The train dropped us off in the heart of historic downtown Winter Park, just a short 300-foot walk from our next stop, The Park Plaza Gardens Hotel. We made our way there but, since it was too early to check in, we left our bags in the lobby and set out to explore. We wandered around, window-shopping and checking out the local restaurants, just killing time until the lunch spots opened.

A Delicious Turkish Lunch at Lale

When the clock finally struck the right hour, we found a Turkish restaurant called Lale. We ordered an assortment of gorgeous appetizers: babaganoush, tzatziki, grape leaves, and homemade lavaash. Paired with Turkish wines, the flavors were exquisite. It was a wonderful treat to savor while we rested from our stroll.

Craft Cocktails and Scenic Boat Tours

Afterward, we bopped around, popping into a few other places and stopping at Prato, a craft cocktail bar, where we tried some unique drinks. Of course, the best part was sharing it all with Tiffany, the love of my life, my perfect travel companion.

As Tiffany had mentioned wanting to check out a particular street, we walked down it and found ourselves at the Scenic Boat Tours. We hopped aboard for a 45-minute tour of three of the seven lakes in the Winter Park chain. The guide shared fascinating stories about the area’s history, the beautiful homes, and Rollins College, which sits on Lake Virginia. We even saw where Mr. Rogers once lived, which was a delightful touch. The boat ride gave us a new perspective on the town, adding a relaxing yet informative layer to our journey. By that point, it was time to check in to our hotel.

The Park Plaza Gardens Hotel, built in 1922, is a historic boutique hotel with timeless charm. It’s the only hotel on Park Avenue, and stepping inside felt like stepping back in time. The tiny, old-fashioned elevator with a cage added to the nostalgic feel. Our room was stunning, with a shared balcony that offered the perfect vantage point to people-watch along Park Avenue.

A quick five-minute Uber ride took us to our dinner destination, Christner’s Steakhouse. Thanks to my good friend Dwayne Gray, I had managed to snag a reservation, and we were treated like VIPs. Dwayne even secured us his personal table, and his favorite server, Melanie, took care of us throughout the evening. Dan, the sommelier, picked out an excellent bottle of wine, compliments of Dwayne, making this meal even more special. Tiffany ordered the filet, and I chose the rack of lamb. Both were cooked to perfection, and the wine was simply divine. Our dinner was not only delicious but incredibly romantic. We couldn’t eat another bite, but Melanie insisted we take some chocolate mousse with us, which we gratefully accepted.

A Perfect 24-Hour Getaway to Winter Park

What an incredibly romantic and exciting 24 hours it was. We packed so much into a single day that it felt as if we’d been there for three. We created memories, made new friends, explored new places, and shared a beautiful journey together. If you ever have the opportunity to visit Winter Park, I highly recommend it. It’s definitely worth it. Special thanks to everyone who took care of us along the way, especially those at The Park Plaza Gardens Hotel and Christner’s Steakhouse. And of course, a heartfelt thank you to Dwayne for everything you did to make this experience unforgettable. Last but not least, thank you, Tiffany, my love, for always making life an adventure.