My Guide to Planning a Speakeasy Weekend

I haven’t organizing many speakeasy adventures across the country, but I’ve been on a couple and talked to several others who have. So I feel I have some pretty good insights on traveling for the modern speakeasy crawl. These are tested and a fun approach to creating an exciting weekend exploring hidden bars and craft cocktails. A key to a successful speakeasy tour is planning, timing, and a sense of adventure. A travel adventure. I like to call it “destination speakeasy.”

I usually start by choosing a city with an existing or up and coming cocktail scene. You can't go wrong with any of the big cities as they each offer a unique twist on the speakeasy concept. The experience isn't just about the mixologist's incredible craft cocktail, but for me, it's the way they preserve the mystique of the Prohibition era drinking culture. Many times reimagined, which I think is cool.

Before traveling for any speakeasy adventure, I dive deep into research mode. I hit my usual Google reviews for locations and ratings and check out what reviewers are saying. Another good place is Instagram spotlights and location tags. I make reservations whenever I can, so I don't waste time standing in line. I even create a spreadsheet of my trips with addresses, hours, dress codes and tips and tricks like secret passwords or entrances. 

One key thing I do is arrange my visits strategically. I map out locations and group venues that are close together. I also don't plan on visiting more than 2-3 venues per evening and I give myself about 1.5-2 hours per location to soak in the atmosphere and enjoy the cocktails. 

My ideal two night adventure usually looks something like this. On the first evening, I start with dinner around 6:00pm near my first speakeasy, hit my first hidden bar at 8:00pm, and move to a second speakeasy around 10:00pm. The second evening usually follows a similar pattern, although I keep my dinner lighter and start the first speakeasy visit around 8:30pm. 

Packing for these trips is pretty easy, although I check out the dress codes before visiting and try to dress up rather than down. Nice cocktail attire is usually classy with dark colors. I try to take a small notebook for jotting down notes, like the atmosphere, customer service, memorable drinks and to not be on my phone. Being on your phone is a big speakeasy no-no. You'll need your phone for taking a few pictures, but if you’re on it, you’re not enjoying the moment and it's disruptive to other patrons. So be mindful of this. 

When it comes to budgeting, it can be pricey, so plan accordingly. I typically set aside about $20 per venue for cover charge in case there is one and I plan to spend about $75-100 per night for cocktails. I prefer using ride-shares after dark, so I factor in transportation costs. I make sure to tip these mixologists as they truly deserve it for the incredible drinks and experiences they create.  

Documenting these speakeasy adventures and trips has become one of my favorite parts of the experience. I like reviewing each speakeasies I visit and I try to take good pictures. This includes a picture of each unique entrance, my favorite craft cocktails. I don’t do it, but one of my friends like souvenirs, so they try to collect menus or coasters whenever they can. 

One cool tip is taking photos of entrance locations during daylight hours because they look completely different at night. It’s also helpful to chat up the mixologists and bartenders and ask them questions about their craft including their recommendations for some of the 'other' best speakeasies in the area.  

Each time I plan a speakeasy weekend, I discover something new. The key to an amazing speakeasy weekend isn't just about the drinks. It’s really the experience and the vibe of speakeasies in different locations and cities. 

This is my simple guide for “destination speakeasy” and traveling to different locations to experience Speakeasy life. Traveling there is half the fun. Finding cool, mysterious and hidden speakeasies with great craft cocktails is the other half. Happy exploring!​​​​​​​​​​​​​​​​