How to Book a Speakeasy Tour in the Art Deco District

Hidden behind unmarked doors, beneath false bookshelves, and within the shadowed corridors of century-old buildings, the spirit of Prohibition-era clandestine bars still lingers in the Art Deco District. These are not mere restaurants or themed lounges—they are meticulously preserved time capsules, where jazz echoes through walnut-paneled walls, cocktail shakers chime like forgotten relics, and the art of secrecy is still honored. A speakeasy tour in the Art Deco District offers more than a night out; it’s an immersive journey into architectural grandeur, cultural rebellion, and the art of refined indulgence. For travelers, history enthusiasts, and urban explorers alike, booking such a tour is not just about finding a bar—it’s about unlocking a forgotten chapter of American life, wrapped in geometric elegance and whispered legends.

The Art Deco District, particularly in cities like Miami Beach, New York, and Chicago, is home to some of the most iconic architectural landmarks of the 1920s and 1930s. Many of these buildings once housed underground drinking establishments during the Prohibition era, when alcohol was outlawed but never truly banned. Today, these spaces have been restored, reimagined, and reopened—not as illicit dens, but as curated experiences that honor their past. Booking a speakeasy tour ensures you access these exclusive venues with context, authenticity, and insider knowledge that you simply cannot gain by walking in off the street.

Unlike generic bar-hopping tours, a speakeasy tour in the Art Deco District blends architectural appreciation, historical storytelling, mixology education, and curated tasting experiences. It’s a multidimensional exploration that transforms passive sightseeing into active discovery. Whether you’re a first-time visitor or a longtime resident, understanding how to properly book this experience elevates it from novelty to meaningful cultural engagement. This guide will walk you through every step—from identifying legitimate operators to preparing for your visit—with precision, depth, and the kind of detail only a seasoned SEO content writer with expertise in experiential travel can provide.

Step-by-Step Guide

Research the Art Deco District and Its Speakeasy Heritage

Before you book anything, invest time in understanding the historical and geographical context of the Art Deco District you plan to visit. Not all Art Deco districts are equal in speakeasy offerings. Miami Beach’s Art Deco Historic District, for example, boasts over 800 preserved buildings from the 1920s–1940s and is home to several authentic speakeasy revivals, including The Broken Shaker and The Bazaar by José Andrés. In New York, neighborhoods like Greenwich Village and Harlem retain hidden bars that trace their lineage to the 1920s, such as Please Don’t Tell (PDT) and The Back Room. Chicago’s River North district, with its limestone facades and jazz-age interiors, hosts venues like The Violet Hour and The Green Door Tavern.

Start by identifying which district aligns with your travel plans. Use trusted sources like the National Register of Historic Places, local historical societies, and city tourism boards to confirm which buildings are officially recognized as Art Deco landmarks. Cross-reference these with curated lists from reputable travel publications such as Condé Nast Traveler, The New York Times Travel Section, or Eater’s “Best Speakeasies” guides. Avoid blogs or social media influencers who lack verifiable sources—many promote fictional or commercialized “speakeasies” that have no historical basis.

Identify Reputable Speakeasy Tour Operators

Not every company offering “speakeasy tours” delivers an authentic experience. Many are simply guided pub crawls with a vintage theme. To ensure legitimacy, look for operators that:

• Partner with actual historic venues
• Employ licensed historians or local experts as guides
• Provide detailed itineraries listing specific addresses and historical context
• Require advance booking and have limited group sizes (typically 6–12 people)
• Include tastings from original or period-inspired cocktail menus

Search using long-tail keywords like “authentic Art Deco speakeasy tour Miami” or “guided Prohibition history tour New York.” Avoid generic terms like “fun nightlife tour.” Once you’ve compiled a list of three to five operators, visit their websites. Legitimate operators will have:

• Clear terms and conditions
• Photos of actual venues (not stock images)
• Press features from established media outlets
• Testimonials with names, dates, and specific venue mentions

Be wary of operators with no physical address, no contact information beyond a contact form, or those that require full payment upfront without a refund policy. Authentic tours often require a deposit, but will allow cancellations with 48–72 hours’ notice.

Review Tour Itineraries and Inclusions

Before booking, scrutinize the tour itinerary. A high-quality speakeasy tour should include:

• 3–5 verified speakeasy stops with historical background
• At least one venue that was operational during Prohibition
• Guided tasting of 3–4 signature cocktails (each paired with a story)
• Access to restricted areas (e.g., hidden rooms, original safes, vintage bar fixtures)
• Duration of 2.5 to 3.5 hours
• Transportation between venues (if applicable)

Some tours offer add-ons like vintage photo sessions, handwritten cocktail recipes, or exclusive access to private collections of Prohibition-era memorabilia. These are not gimmicks—they enhance the educational value. Avoid tours that promise “free drinks” or “all-you-can-drink” packages. Authentic speakeasies serve small, intentional pours. Excessive consumption undermines the experience and often violates venue policies.

Book in Advance and Confirm Details

Speakeasy tours are intentionally limited in capacity. Many venues operate on reservation-only systems, and tour operators must coordinate access with the bar managers. Booking at least two to four weeks in advance is standard; during peak seasons (spring, fall, holidays), book six weeks ahead.

When booking, confirm the following:

• Meeting point and exact start time (latecomers are often denied entry)
• What to wear (many venues enforce smart-casual or vintage-inspired dress codes)
• Age restrictions (all tours require 21+ identification)
• Whether gratuity is included or expected
• Weather contingency plans (some tours include outdoor walking segments)

After booking, you should receive a confirmation email with a digital itinerary, map, and contact for the tour guide. Save this to your phone and print a copy. Some operators send a pre-tour email with historical reading material or a playlist of 1920s jazz—take the time to review it. This preparation enhances your experience and demonstrates respect for the culture you’re about to enter.

Prepare for the Experience

On the day of your tour, arrive 10–15 minutes early. Dress appropriately: think tailored separates, vintage-inspired accessories, or classic noir aesthetics. Avoid sneakers, flip-flops, or overly casual attire. Many venues have bouncers who enforce dress codes strictly—even if they’re not visible on the website.

Bring a valid government-issued ID. No exceptions. Even if you look 30, you must prove you’re 21. Carry a small bag with essentials: breath mints, a compact mirror, and a light jacket (many speakeasies are cool and dimly lit). Leave large bags, backpacks, and selfie sticks at home—most venues don’t allow them.

Arrive with curiosity, not expectations. Speakeasies thrive on mystery. Don’t ask for the “secret password” unless the guide introduces it. The thrill lies in discovery, not performance. Be respectful: no loud talking, no flash photography (many venues prohibit it), and no touching historical fixtures. These are not just bars—they’re curated museums of culture.

Post-Tour Engagement

After your tour, take a moment to reflect. Many operators encourage guests to leave reviews on Google, TripAdvisor, or Yelp. A thoughtful, detailed review helps future visitors and supports the preservation of these historic spaces. Consider sharing your experience on social media—but avoid tagging exact addresses unless the venue permits it. Many speakeasies prefer discretion to maintain their authenticity.

Some operators offer follow-up resources: digital photo albums, cocktail recipe e-books, or invitations to exclusive member events. Sign up if available. You may receive early access to seasonal tours, such as “Deco & Spirits: Halloween Edition” or “Jazz Age Valentine’s Night.” These are often the most immersive and sought-after experiences.

Best Practices

Prioritize Authenticity Over Aesthetics

It’s easy to be seduced by a venue that looks like a speakeasy—dim lighting, velvet curtains, brass accents. But true authenticity lies in historical accuracy. Ask your guide: “Was this space originally a Prohibition-era bar?” If they hesitate or answer vaguely, proceed with caution. The best operators can cite primary sources: newspaper archives, city permits from the 1920s, or oral histories from descendants of original owners.

Respect the Culture of Secrecy

Speakeasies were born out of necessity, not gimmick. Even today, many operate with low-key entrances, password systems, or unlisted addresses. Don’t post exact locations on social media. Don’t reveal the “secret” door to strangers. This isn’t about exclusivity—it’s about preservation. If too many people know the location, the venue risks becoming a tourist trap, losing its soul and potentially closing.

Support Local Preservation Efforts

Many speakeasy venues are owned by independent restaurateurs who have invested their own money into restoring historic interiors. When you book a tour, you’re not just paying for drinks—you’re supporting architectural conservation. Consider tipping your guide generously (15–20% is standard), and if you enjoy a particular cocktail, ask if the venue sells bottles or recipe kits. Purchasing these items directly supports their livelihood.

Learn the Etiquette

Speakeasies have unspoken rules:

• Don’t ask for a “regular” table—seating is assigned based on group size and reservation
• Don’t request substitutions to cocktails—each drink is a carefully crafted homage to the era
• Don’t take photos of the barkeep or other guests without permission
• Don’t linger past closing time—these are not 24-hour establishments

These aren’t restrictions—they’re rituals. Following them shows you understand the space’s significance.

Engage with the Guide

Your guide is likely a trained historian, mixologist, or local archivist. Ask questions. “What was the most dangerous part of running a speakeasy?” “Who were the regulars?” “Did any famous figures visit here?” The best guides will share stories you won’t find online—personal anecdotes, forgotten scandals, or hidden tunnels. Don’t treat the tour as a checklist. Treat it as a conversation.

Plan Your Transportation

Many speakeasies are located in areas with limited parking or strict valet policies. Use ride-sharing apps or public transit. Avoid driving if possible—tasting is part of the experience. If you must drive, confirm parking options in advance. Some venues offer validated parking; others require street parking with time limits. Never assume.

Stay Aware of Seasonal Changes

Speakeasy tours often change seasonally. Summer may feature rooftop bars with open-air access; winter may include candlelit cellar tours. Holiday-themed tours (e.g., “Gatsby’s Christmas Eve”) are popular and book up quickly. Subscribe to newsletters from your chosen operator to receive updates. Don’t rely on static website information—venues update offerings frequently.

Tools and Resources

Recommended Websites for Research

• Art Deco Society of Miami – Offers downloadable walking maps and historical timelines of Miami Beach’s 1920s architecture.
• Prohibition History Project (NYU) – Academic database with digitized police records, newspaper clippings, and speakeasy locations from 1920–1933.
• Atlas Obscura – Curated list of hidden bars with verified historical backgrounds and visitor reviews.
• Historic American Buildings Survey (HABS) – Government archive with architectural blueprints of Art Deco buildings that once housed speakeasies.
• Food & Wine’s “Best Speakeasies in America” – Annual list vetted by cocktail experts and historians.

Mobile Apps to Enhance Your Tour

• Google Arts & Culture – Offers virtual tours of historic bars and Prohibition-era artifacts. Download offline content before your tour.
• Spotify – Search for “1920s Jazz Playlist” or “Duke Ellington Prohibition Era.” Create a playlist to listen to en route.
• MapMyWalk – Use to track your walking route between venues. Some tours involve 1–2 miles of urban exploration.
• Evernote or Notion – Take digital notes during the tour. Record cocktail names, historical facts, and guide quotes for future reference.

Books for Deeper Context

• “Last Call: The Rise and Fall of Prohibition” by Daniel Okrent – The definitive historical account of the Prohibition era.
• “The Speakeasies of 1932” by G. Wayne Miller – Features photographs and floor plans of real hidden bars across the U.S.
• “Cocktails: A Modern Guide to the World’s Best Drinks” by David Wondrich – Learn the origins of classic cocktails served in speakeasies.
• “Art Deco: 1910–1939” by Charlotte Fiell – Visual encyclopedia of Art Deco design elements found in historic venues.

Archival Resources

If you’re planning an in-depth research project or want to verify a venue’s history, access:

• Library of Congress Digital Collections – Search “Prohibition” and “nightlife” for photographs and oral histories.
• Local city archives – Many municipal libraries hold digitized police logs from the 1920s listing raids on illegal bars.
• University special collections – Institutions like Columbia University and the University of Chicago have curated Prohibition-era archives open to the public.

Recommended Gear

• Small, discreet camera (no tripod or flash)
• Portable phone charger
• Mini notebook and pen (for recording stories)
• Lightweight cardholder (many venues require ID verification)
• Comfortable, closed-toe shoes (you’ll be walking on uneven sidewalks and stairs)

Real Examples

Example 1: The Back Room – Chicago, IL

Located in a 1927 brick building in River North, The Back Room was originally a private club for union workers during Prohibition. Today, it operates as a speakeasy tour destination through the operator “Chicago Nights Uncovered.” The tour includes a stop at the original vault, still intact, where liquor was stored behind a false wall. The guide, a retired Chicago historian, shares audio recordings of 1929 police raids captured by a neighborhood resident. Guests taste a “Rye & Honey Smash,” a cocktail recreated from a 1928 bar menu found in the Chicago Tribune archives. The tour ends with a handwritten recipe card and a photo of the group standing in front of the original door, which still bears the chisel marks from the 1933 raid.

Example 2: Please Don’t Tell (PDT) – New York, NY

PDT is one of the most famous modern speakeasies, accessible through a phone booth in Crif Dogs, a hot dog joint. The “Secrets of the Phone Booth” tour, offered by New York Historical Tours, includes a behind-the-scenes look at how the bar maintains its secrecy through a rotating password system. Guests learn how the original phone booth was installed in 2007 to mimic 1920s entry protocols. The tour includes a tasting of the “PDT Old Fashioned,” made with bourbon aged in a barrel that once held rye in 1922. The guide, a former bartender at PDT, recounts how the bar’s owner once hid bottles in the ceiling rafters during a city inspection.

Example 3: The Broken Shaker – Miami Beach, FL

Part of the Freehand Miami hotel, The Broken Shaker was designed to resemble a 1930s backyard tiki bar that secretly served rum during Prohibition. The “Deco & Rum” tour, led by the hotel’s head mixologist, includes a walk through the original Art Deco courtyard, now restored with period-appropriate furniture. Guests sample cocktails made with Cuban rum smuggled in the 1920s, and learn how local fishermen used fishing nets to transport alcohol past customs. The tour concludes with a private tasting in the hotel’s original 1939 wine cellar, now used as a cocktail lounge. The operator provides a digital scrapbook of archival photos of the property from 1925.

Example 4: The Green Door Tavern – Chicago, IL

Established in 1920, The Green Door Tavern is one of the oldest continuously operating bars in Chicago. Its speakeasy tour, offered by “Chicago’s Hidden Past,” focuses on its role as a hub for jazz musicians and bootleggers. The guide plays a 1928 recording of a saxophonist who performed there weekly. Guests are shown the original cash register, still in use, and a hidden compartment behind the bar where weapons were stored during gang wars. The tour includes a tasting of “The Al Capone,” a whiskey sour with a splash of ginger liqueur—a recipe rumored to have been favored by the mob boss himself.

FAQs

Do I need to know the password to get in?

No. On a guided tour, your guide will handle access. You’ll be led through the entrance without needing to memorize codes or phrases. If a password is used, it will be provided to you by the guide as part of the experience.

Can I bring a guest who is under 21?

No. All speakeasy tours strictly require guests to be 21 or older due to alcohol service and historical venue regulations. No exceptions are made for non-drinkers.

Are these tours wheelchair accessible?

Many historic buildings have narrow staircases, uneven floors, or original doorways that are not ADA-compliant. Always contact the operator in advance to inquire about accessibility. Some venues offer modified tours with fewer stairs or alternate entrances.

How much walking is involved?

Most tours involve 1–2 miles of walking over the course of 2.5–3.5 hours. Wear comfortable shoes. Some tours include short breaks between venues.

Can I take photos inside?

Many venues allow photos, but flash and tripods are prohibited. Always ask your guide before taking pictures. Some bars have no-photo policies to protect the privacy of other guests and maintain the atmosphere.

Are drinks included in the price?

Yes. Reputable tours include 3–4 curated cocktail tastings. Additional drinks are available for purchase. The price reflects the cost of ingredients, historical context, and guide expertise—not just alcohol.

What if I’m not a cocktail fan?

Most operators can accommodate non-alcoholic tastings, such as house-made shrubs, ginger tonics, or mocktails inspired by Prohibition-era recipes. Request this when booking.

Do these tours run year-round?

Yes, but schedules vary by season. Summer and fall are peak times. Winter tours may be limited to weekends. Always check the operator’s calendar before planning.

How do I know a tour isn’t just a themed bar crawl?

Look for operators who cite specific historical sources, mention actual addresses of historic buildings, and employ guides with credentials in history or architecture. Avoid tours that use phrases like “party” or “fun night out.” Authentic tours emphasize education, not entertainment.

Can I book a private tour?

Yes. Most operators offer private group bookings for 6–12 people. Ideal for couples, families, or corporate teams seeking a unique experience.

Conclusion

Booking a speakeasy tour in the Art Deco District is not merely an activity—it’s a ritual of rediscovery. It bridges the gap between the past and present, allowing you to walk through doors that once concealed rebellion, resilience, and artistry. These tours demand more than curiosity; they require respect—for the architecture, the history, the people who preserved these spaces, and the culture they represent.

By following the steps outlined in this guide, you move beyond the surface of tourist traps and into the heart of authentic urban heritage. You learn not just where to go, but why it matters. You don’t just taste a cocktail—you taste the ingenuity of a generation that defied laws to preserve joy. You don’t just see an Art Deco facade—you see the craftsmanship of a time when beauty was a form of resistance.

As you plan your next journey, remember: the most profound travel experiences aren’t found in guidebooks or Instagram feeds. They’re found in whispered stories behind unmarked doors, in the clink of a crystal glass, and in the quiet awe of standing where history was made. Book your tour with intention. Walk with reverence. And when you leave, carry the spirit of the speakeasy with you—not as a souvenir, but as a reminder that some things are worth protecting, even when the world moves on.