Inside: Run away with us to the 1920’s as we step back in time to enjoy the magic of a hidden bar, Art Deco jewelry, and sexy cocktails. You need to put this speakeasy-themed weekend in Cleveland on your list!
What is it about the 1920’s? I’ve long been obsessed with this time period. Partially because I identify with writers like F. Scott Fitzgerald. I see myself empathizing with this “lost generation” – this sort of wandering, disoriented and directionless feeling that was so common.
As Columbus native James Thurber famously wrote: “You are all a lost generation,” Gertrude Stein said to Hemingway. We weren’t lost. We knew where we were, all right, but we wouldn’t go home. Ours was the generation that stayed up all night.
I also deeply love how the attitudes had started to change in this time period. Black culture was becoming more mainstream, with it came soulful jazz and poetry and writers with something new to share. Women had gotten the vote, and Margaret Sanger was enlightening the world about birth control, so finally we could all start having sex for fun instead of for procreation.
Art Deco was in style, and people decorated their homes with jewel-toned walls, rich textiles, and hints of gold. And my husband has always been interested in craft cocktails and their colorful history. Prohibition cocktails and hidden bars are the sort of thing that keeps him up all night.
So I decided to surprise him with a speakeasy-themed weekend away. I kept the whole weekend a surprise and he loved every minute. We stayed at a vintage glam hotel, visited an amazing speakeasy, and had a romantic picnic in our hotel room at midnight.
Our Speakeasy-Themed Weekend in Cleveland
Before our trip, I ordered a few things to help set the mood. Fashionista I am not, but there’s something really fun about dressing the part. You may already have some pieces that would work, but here’s what I recommend:
A cute pair of Art Deco earrings.
A Flapper-style dress.
I was a bit torn between two dresses, so I got them both. One is a bit more whimsical, the other a bit more understated. I really loved this peacock design. I mean….how amazing is this dress?
The other dress that I loved was this simple black one. I was channeling my inner flapper, so I decided to be a bit impractical and get both dresses, but if I had been my usual (practical) self, I would have just gotten this one as it’s basically a little black dress you can wear anywhere.
And I’m almost too embarrassed to tell you the last thing I bought, but, here goes. A copy of the book “Dear Scott, Dearest Zelda.” It’s basically a collection of the love letters they wrote to one another and I’ve borrowed a copy from the library so many times that I just finally bought it for my home library. I’m a little obsessed with their story, and reading these letters just makes my heart melt.
And as my husband drove, I read to him from the book. I know, I know, I’m so damn cheesy. But I can’t help it and he loves me anyway.
I read excerpts like:
“Why is there happiness and comfort and excitement where you are and no where else in the world?”(Zelda to Scott)
“You are the finest, loveliest, tenderest, and most beautiful person I have ever known—and even that is an understatement.” (Scott to Zelda)
“Excuse me for being so intellectual. I know you would prefer something nice and feminine and affectionate.” (Zelda to Scott)
Speakeasy-Themed Hotels: Best Places to Stay for a Vintage Glam Weekend in Cleveland.
I opted for a stay at the Hyatt Regency Cleveland at the Arcade. I was reading reviews of the hotel, and came across a review that mentioned that they felt like it was a scene out of the Great Gatsby. And they weren’t wrong. This hotel is simply stunning. With an onsite spa, restaurant, lounge, and gorgeous design, you’ll fall in love with the Hyatt Regency Cleveland at the Arcade.
This historic hotel, located in downtown Cleveland, is inside of a building that was constructed in 1890. Even if you don’t spend a night in this hotel, I highly recommend a walk through the magnificent space. The glass and gold and wood paneling are just mesmerizing. It’s definitely a vintage glam feel.
The other hotel that I considered was the Metropolitan at the 9. This gorgeous hotel is part of the Autograph Collection of Marriott Hotels. More modern than vintage, this hotel is all about the glam. I’m basically a sucker for the Autograph Collection – selected hotels that are rich in craft and character, design, architecture and delightful histories. The location of this downtown hotel is perfect, and many of the things we did were actually located inside this hotel.
With a rooftop bar, fancy restaurants and jaw-dropping views of the city, the Metropolitan at the 9 is pretty perfect for a speakeasy-themed weekend away.
Once you’ve checked into the hotel and dropped off your bags, I highly recommend taking a stroll through downtown Cleveland. We walked, hand-in-hand, and admired the stunning architecture.
My husband went to Case Western Reserve and had spent a fair amount of time exploring downtown Cleveland. It was really fun looking at the old buildings. There is so much history here. We also made a quick stop into the Heinen’s grocery store. It’s attached to the Metropolitan at the 9 hotel and definitely worth a stop.
The Heinen’s Market is in an old bank. We were walking around taking pictures of the beautiful stained glass windows and I was carrying on and super excited, and the manager saw us and asked if we’d like a quick tour of the back. The back offices were built into the old bank vaults and it’s such a neat building.
I knew that we’d be spending a lot of time drinking this weekend, because after all, I was channeling my inner Zelda Fitzgerald and I thought it might be fun to opt for a midnight picnic in our hotel room. I had packed a pair of crystal champagne flutes we had gotten as a gift for our wedding and picked up a bottle of champagne, a loaf of baguette, some cheese and fruit, and a few deli salads to bring back to our room.
Speakeasy-Themed Weekend in Cleveland: Where to Drink
Let’s get right to it. If you’re planning a 1920’s Prohibition themed weekend, there will be cocktails. We planned our entire evening around craft cocktails.
Our favorite spot was an actual speakeasy bar! This gorgeous space beneath the Cleveland Trust Rotunda is home to an upscale, craft cocktail bar. Located inside the Metropolitan at the 9, this space is also walking distance from the Hyatt Regency at the Arcade.
This sexy bar is also located inside the Metropolitan at the 9. Artisan cocktails and an intimate setting make this a perfect stop.
Society Lounge Cleveland
We didn’t make it to this ultra glamorous bar, but it was on my list and worth a mention. It’s a bit of trek so I would recommend grabbing an Uber if you plan to hit this spot.
The Chocolate Bar
If you’re looking for something a bit more fun, or you’re not into the strong, prohibition-style craft cocktails that my husband obsesses over, you might like a stop at the Chocolate Bar. Located inside the Hyatt Regency Cleveland at the Arcade, you’ll find sweet libations like birthday cake, black-forest, and chocolate mint martinis.