During our Key West (Florida, USA) 10-day vacation we found a few sites with pinball, and other surprises. To get the complete list of pinball locations in Key West, and more details, please consult the Pinball Map.
The Dive Bar Shirt Club – Grub House
Location: 320 Grinnell St, Key West, FL 33040 (Seaport)
Phone: +1 (305) 517-6898
Website: divebarshirtclub.com/pages/bars
Open daily from 11am to 11pm
Please check the Pinball Map for the current game line-up.
For an area that has so many bars and related entertainment, there are only a few places left in Key West that have pinball on site. One of these is The Dive Bar Shirt Club – Grub House which is the home of The Dive Bar Shirt Club, a monthly subscription club that sends its members T-shirts from real dive bars across the United States.
Cody Shoemake and Mike Edwards founded The Dive Bar Shirt Club in January 2009. For $22 a month, aficionados receive a shirt in the mail featuring the logo of a different dive bar—a watering hole that typically prides itself on its history and love of drinking—chosen by Shoemake. The bars send in their logos and they’re applied to shirts by Shoemake; to ensure members get a unique shirt, only bars that don’t sell their shirts online will be considered.
Club members celebrate a different dive bar with a limited-edition shirt each month. Once the shirts are gone, they are gone for good. Photos of ‘retired’ shirts are available for viewing on the website mentioned above.
However, no membership is required to obtain the Grub House merch; hats, shirts, glassware and other assorted items are for sale at the bar. An example is the official hat of the Grub House below.
On the ceiling of the bar they have T-shirts of the month from the past for you to admire. The public is invited to to drink at the bar or on their patio. After 5pm the bar area is restricted to patrons 18-years-old and over.

The bar generally has six local beers on tap and a pair of macro-brews such as Guinness and Fat Tire. An assortment of canned and bottled popular beers and wines by the glass are also available.
They have a limited food menu featuring Dive Bar Tacos (ground beef or chicken), brisket tacos, grilled burritos, and corn chips with your choice of queso or salsa. The kitchen closes at 9pm, so be aware of that.
The entertainment consists of live music most weekends, a library of board games…
…a monthly Team Jigsaw puzzle race called Puzzle and Guzzle…
…and, of course, pinball!
There are generally four pinball games on hand; during our visit the choices were all recent Stern titles decked out with premium options and even toppers! The games were in immaculate condition and played perfectly. $1 per credit, quarters only, with change available from the bartender if needed.
We ran into these characters at The Dive Bar Shirt Club visiting Key West from Chicago!

The Stern gang was on hand in Key West in support of the second annual Q-West (pronounced Quest) comedy escape weekend hosted by comedian Brian “Q” Quinn at the Key West Theatre.
Quinn is the host of a cable television show called Impractical Jokers which has a growing following of 30-somethings. The ‘Escape Pass’ tickets for the event were sold out almost as soon as they went on sale at Eventbrite and cost from $500 per person (VIP access somewhat more).
In addition to Stern being a lifestyle sponsor for Q-West 2, they also had a pop-up free play arcade at Lost Boys Creations just off of historic Duvall Street. More about that further on in this article.
The Dive Bar Shirt Club has the previously mentioned bar area with retro-styled tables and seating from 1960s-1970s bowling alleys, etc.
The bar area also has an interesting collection of antique porcelain and neon signage for you to enjoy.
The patio area is ideal for families with young children and dogs, while the upstairs area is where the live music can be found on most weekends.
Finnegan’s Wake Irish Pub was a dive bar that was mostly frequented by locals and unfortunately closed in 2022. The Dive Bar Shirt Club hosts a street festival the weekend of St. Patrick’s day to remember it, with live music beginning at noon each day.
The motto of the fest is “Come for the food, stay for the beer, leave with the staff”.
Legend has it (unconfirmed) that Finnegan’s Wake Irish Pub was where Jimmy Buffet drank his first beer in Key West.
Overall we felt that The Dive Bar Shirt Club was a great place to visit during our stay in Key West.
Perhaps it could be the first place to visit to set the proper party mood? The fact that they have a good selection of the latest games available to play is a welcome bonus.
Lost Boy Creations
Custom Adventure Outfitters, Surf and Paddle Shop
Location: 417 Southard St, Key West, FL 33040
Phone: +1 (305) 741-7680
Website: lostboycreations.com
7 days a week: 9am – 9pm
Lost Boy Creations is a wanderlust lifestyle goods shop with hats, men’s & women’s apparel, and one-of-a-kind items from local artists.
Something that I found quite interesting is that Lost Boy Creations has their own bar! Only a few drink selections were available, but it is nice that they offer beverages for shoppers or to keep spouses entertained while the ‘other’ in the couple shops. After a certain number of adult beverages, Lost Boy’s prices probably don’t seem as onerous.
Thoughtfully, drink holders were provided for the pinball games at Lost Boy.
Lost Boy Creations also has their own podcast Get Lost; A Podcast with Friends recorded in store where the latest lifestyle fashions, music and whatever comes to mind are discussed. The most recent podcast featured guest Tom Dustin who is a stand up comedian, and owner of Comedy Key West. His new film, Tom Dustin, Portrait of a Comedian, directed by fellow comedian Joe List, is showing in select theaters as of April 25.
Also on the podcast page are links to Rock in the Shop, a series of recordings of performances from the Lost Boy Creations ‘shop’.
Lost Boy has the official Q-West 2 merch available for purchase on their website if you neglected to get yours during the Comedy Escape Weekend, or to fool your friends into thinking you had the Benjamins to attend the event in person.
We were invited to the pop-up by the Stern folks and witnessed the recording of the last of a series of short videos done by Jack Danger and crew. These videos are snippets from their visits to most of the sites in Key West that have pinball. These videos are available for viewing on Stern Pinball’s Instagram, YouTube channel and Stern Pinball’s Facebook page under ‘Reels’.
As mentioned previously, Stern Pinball had a ‘pop-up’ free play arcade at Lost Boys with a few of Stern’s latest titles, including Pokemon.
Stern set up an Insider Connected scoreboard for a high score tournament for prizes during the Comedy Escape Weekend.
Even if you didn’t manage a high score, Insider Connected members could earn a Q-West 2 IC badge just by playing.
Some of the comedians involved with Q-West 2 showed up randomly at Lost Boy in-between shows, which we felt was definitely fun.
Hats off to Stern Pinball for partnering with Q-West comedy escape weekend and Lost Boy Creations to bring the latest pinballs to the public.
Hopefully there will be more of this type of Stern pop-up event in the future.
Some images used in this review were furnished by The Dive Bar Shirt Club and are used here with permission.
Additional information on Quinn and the reasoning behind hosting a small comedy festival in Key West can be found in this article: entrepreneur-resources.net/brian-quinns-q-west-comedy-festival-why-capping-attendance-at-200-creates-higher-value-fan-experiences

























