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Step into Key West’s rum-running past on a 90-minute walking tour that ends with a drink at Sloppy Joe’s and the bar’s Annual End of Prohibition Party. Small groups, real crimes, and waterfront streets make this a compact, memorable slice of island history.
Step into Key West’s rum-running past on a 90-minute walking tour that ends with a drink at Sloppy Joe’s and the bar’s Annual End of Prohibition Party. Small groups, real crimes, and waterfront streets make this a compact, memorable slice of island history.
Book with Tart Tales, LLC
Verified experiences and guided adventures in the surrounding area.
Operated by Tart Tales, LLC · Key West, Florida
Sloppy Joe's Prohibition Tour! takes you onto Key West’s waterfront streets for a 90-minute, under-a-mile walk that reads like a crime scene map of rum-running, smuggling, and island lawlessness. Meet your guide at 308 Front Street with iWITNESS True Crime Tours and move through the low-slung storefronts, cobbled sidewalks, and harbor-facing alleys that once doubled as drop points for cutters and rum chasers. The route finishes at Sloppy Joe’s Bar, where the program folds into the bar’s Annual End of Prohibition Party with a complimentary drink and a staged surprise.
This tour is compact by design. Small groups—capped at 15 witnesses—mean you get front-row listening and the chance to ask pointed questions about the real crimes behind Key West’s legend. The storytelling zeroes in on actual locations and documented smuggling operations; you’ll stand where registries, bar tabs, and contraband intersected with local life. Although the tour is theatrical in tone, it’s grounded in historical practice: Key West was a prime rum-running corridor during Prohibition, and the island’s architecture and harbor access shaped those illicit routes.
What makes this offering special is the combination of place and personality. iWITNESS True Crime Tours trades general history for scene-specific testimony, and Sloppy Joe’s Bar supplies an authentic finish—an active venue with its own long public presence on Key West’s social map. The timing matters: this December 5 event ties a modern crowd to a particular moment in American legal history while delivering island humor and grit.
Practical details are straightforward: easy walking for roughly 90 minutes, less than a mile total; age minimum 17; small-group format; casual footwear recommended for uneven sidewalks. Bring ID if you plan to drink at the finale and cash for gratuities. Rain will not cancel—come with a jacket or umbrella. Photos are allowed, and the tour is accessible, so all can take part.
If you’re staying in Key West to sample its maritime past, this short tour is an efficient way to deepen your understanding of how Prohibition reshaped coastal communities—and to do it in good company, with a drink at the end. Reservations are limited; the package sells out for themed events like the Annual End of Prohibition Party, so book early to secure a slot on this very particular slice of island history.
Meetup is at the foot of the stairs at Surly Siren Saloon, 308 Front Street, where guides check names and set expectations before walking. The program favors eyewitness detail over speculation; expect crisp narration, slang, odd sardonic aside. Because the tour ties into a live bar event, plan for crowds at the finish and bring patience ordering drinks. The tour’s small scale makes it ideal for history-minded travelers who prefer conversation to crowds.
Less than a mile total—an easy urban stroll through Key West’s waterfront streets.
90 minutes; the tour is designed to be compact and information-dense.
Groups are small, capped around 15 participants to keep the experience intimate.
No. The tour is rated 17+ and is not suitable for children under 17.
Yes. The tour is accessible, though some historic sidewalks may be uneven—notify the operator if you need assistance.
Comfortable shoes for walking, light layers for changing weather, and a rain jacket if showers are forecast.
Tart Tales, LLC is a Key West, Florida-based tour company specializing in guided walking tasting experiences focused on the island’s signature Key Lime dessert and local history. The company offers four distinct 1.5-hour tours — Bahama Village Adventure, Southernmost Saunter, Tarts & Tales Tour, and Historic Seaport Stroll — each pairing samples of three variations of Key Lime Pie with a refreshing Key Lime Cocktail. Tours take place in Old Town Key West, including Bahama Village, Duval Street, and the historic waterfront, and blend culinary tasting with storytelling about local landmarks and legends. Guides lead small groups along scenic streets while presenting historical context and flavor notes for each sampled tart. The tasting format highlights differences in crusts, fillings, and presentation across local bakeries and eateries, giving guests a comparative dessert experience. The Historic Seaport Stroll additionally appears as part of TuTu Tart Tours on select dates, offering the same 1.5-hour tasting and interpretive walk along the waterfront. Tart Tales, LLC emphasizes an accessible, leisurely pace suitable for visitors wanting a short cultural and culinary introduction to Key West. Reservations typically specify tour selection and date; tours are timed to balance tasting portions with walking segments. The company’s offerings provide an easy way to taste Key West’s iconic dessert while learning neighborhood history. Tart Tales, LLC is presented as a local business operating in Key West, Florida, that curates pie tastings paired with a cocktail on guided walking tours. Bookings are available year-round subject to advertised tour schedules and availability updates.
Book with Tart Tales, LLC