Orlando: The last time I was there was probably a decade or so ago when my parents took me on that ever-so-important childhood trip to Disney World. Even at the age of twelve, I wasn’t a big fan of the experience – long lines, hot weather, and those massive turkey legs that are larger than a child’s torso. Perhaps I’ve become sour with old age, but the pictures that sit in the family scrapbook of the excursion features a child (me) with a not-so-pleasant facial expression.
When I was given the opportunity to travel to Orlando for a long weekend, I had my doubts. Of all the places I could go in the state of Florida – Palm Beach, St. Petersburg, hell even back to Miami – why in the world would I go to the city filled with a bunch of amusement parks and (even worse) children? But, in typical Dean-fashion, I shrugged, said “What the hell,” and packed a bag (or two) for a long-weekend.
Going back to Orlando as an “adult” was admittedly quite different this time around. For starters, I rarely find myself greeted by a blacked-out extended-length Audi in the pick-up lane of the airport (special thanks to the concierge at Waldorf Orlando for the bougie ride). Usually it’s some random Uber “driver” that looks out the window with some pained expression – either because he knows I’m a bit of prick based on my low Uber score or because of the cart of luggage I haul in front of me. Perhaps it’s a combination of the both?
Transportation aside, Orlando surprised me – in a very pleasant way. I got to be a part of some incredible experiences and meet some really fascinating people. As I get “older” (as nauseating as that may sound for someone who was born in ‘94), I find myself wanting less “things” and more experiences. It’s the story behind something that creates a sense of pricelessness in my eye and that’s exactly what I found in Orlando.
Below I’ve noted some of the highlights of my trip along with two additional guides curated specifically for The Waldorf Astoria – one for Winter Park and the other for Orlando. For the full details about my stay on their property, take a read of My Waldorf Weekend featuring the best gin & tonic that I’ve had in my life.
# One // Waldorf Astoria Orlando
What. A. Stay. It takes a lot for me to feel guilty and the Waldorf Astoria accomplished that the moment I got there. From tasting menus to mixology classes to having the opportunity to explore the area of Orlando, the trip was an incredible experience from start to finish. Special thanks to everyone there that made for the most memorable of weekends.
# Two // Carousel Emporium
A little north of the heart of Orlando sits The Carousel Emporium. When I entered I was greeted by one of the owners, Sara. Like everything in the shop, she was one-of-a-kind. She’s quick and smart with a personality that readers “no bull-shit.” Sara went to school for the arts, served in the Navy (get that part wrong and she’ll give you a look that’ll make you want to hide underneath one of the antique tables in there), worked in real estate, and now owns an antique store. While her mother hated antiques, her grandmother loved them that ultimately placed her where she is today. The shop is filled with furniture and antique barware with origins from the North. Favorites included a green set of liqueur drinking glasses, a needlepoint footstool, and a Waterford crystal decanter. It’s a good thing American Airlines manhandles passengers’ luggage like they’re busheling hay or I would have bought all three and checked them in at the airport.
# Three // Siegel’s
I had a bit of time to kill when I landed on Friday so I went into the Siegel’s in downtown Orlando and was greeted by the shopkeeper - Lance Powers – who was tailoring a shirt on a table that looked older than him. You know those people who are just overly nice and genuinely happy with their life? That’s Lance. He’s worked in menswear his entire life and absolutely loves it. We ended up having a good thirty-minute conversation after he told me a story about making a sale at the country club (if you can even call it that) in the town I’m from. It was a serendipitous moment that reminded me how bizarrely small the world is. The Siegel’s shop was beautiful and had a fantastic collection of garments and neckwear, but Lance was definitely the coolest thing about the place.
# Four // Gold Phoenix Antiques & Gifts
This place was a gem. It was around the corner of the Carousel Emporium and was stuffed to the ceiling. You had buckets filled with silver utensils, old history books from France, and a set of European cavalry prints that I didn’t have the strength to pass up. They were just small enough that I was able to wrap them in a couple inches of bubble wrap, slip them into my big LL Bean Boat & Tote, and carry it onto the plane back to DC. While the Golden Phoenix may be small, it has plenty to offer. I could have spent an hour inside had I not needed to be somewhere else.
# Five // Gin & Tonic
It’s pretty obvious that I love gin…a lot…so when the sommelier at my dinner at Bull & Bear mentioned that I needed to try their take on the classic cocktail it was an immediate yes. I posted this on my Instagram, but I have to mention it again because it’s (quite literally) the best gin & tonic I’ve ever had in my life. The cocktail features a generous pour of Monkey 47 gin with tonic ice cubes floating amidst a handful of herbs that complement the distillation of the gin. It was incredible…
# Six // Winter Park, Florida
I spent the majority of my Saturday in Winter Park. The city is about thirty or so minutes away from the hotel and was filled with awesome finds. You can see my full guide for the city here, but top stops included The Morse Museums (they have the largest collection of Tiffany glass in the world); John Craig Clothiers (super cool menswear store that was actually recognized on Esquire’s Retail 100 list); and lunch at Prato featuring the best truffle chips I’ve ever had. Oh…and dogs…lots and lots of dogs. Shout out to Isabella D. for being my last-minute tour guide for the city.
# Seven // Cocktail Creations @ Bull & Bear
After my day in Winter Park, I attended the Waldorf’s Cocktail Creations class at their hotel bar. Since I’m much better in partaking rather than making, it was a good use of time. My biggest takeaway from the experience is that I’ve been using mint the wrong way. Fun fact: The true “value” of the garnish is within the skin of the leaf that releases aromatic oils. The best way to get them is not to muddle, but to place the leaf in the palm of your hand and clap. Special thanks to Rafael – the GM at Buller & Bear – for helping me move past my ignorance…and letting me make a second cocktail.
# Eight // Jim Roberts Photography
I hate having my photograph taken – there’s a reason why I do all those profiles – but as I was walking to The Imperial Wine Bar (really cool furniture/bar hybrid concept) I came across this cozy photography studio by Jimm Roberts. I couldn’t help but snap a picture and include it in here.
# Nine // Golf Cart Joy Riding
Who doesn’t love a ride on a golf cart? After looking out to the course every morning from half a dozen panoramic windows in my room, I decided to sneak down to snag a set of wheels. The course was beautiful and having lived in the middle of DC for the past four years, I sort of forgot what it was like to be around nature. This rabbit was about four feet away from me during my ride and (graciously) allowed me to snap a picture.