BOSTON GUIDED TOUR FIELD GUIDE

Prohibition After Dark: A Three‑Stop Speakeasy Crawl Through Historic Boston

A 3‑hour guided walk led by Rum Runner Speakeasy Tours that stops at three historic speakeasies for Prohibition stories and a signature Rum Runner cocktail—this guide explains what to expect and how to prepare.

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Prohibition After Dark: A Three‑Stop Speakeasy Crawl Through Historic Boston.

Duration

3 Hours

Location

Boston

Operator

Rum Runner Speakeasy Tours

Outing Highlights

THE HISTORY

Prohibition-era lore brought to life

The tour traces Boston’s illicit 1920s—rum-running, political corruption, and the underground drinking culture—through narrative-rich stops in vintage-style bars.

THE COCKTAIL

A signature Rum Runner

At one stop guests enjoy the Rum Runner signature cocktail that anchors the experience’s blend of history and hospitality.

THE VENUES

Three intimate, carefully selected speakeasy bars

The operator assembles three historic speakeasies with vintage atmosphere to showcase different facets of Boston’s Prohibition-era nightlife.

What the day feels like

What the evening feels like

Part history lesson, part cocktail experience, the guided walk moves through three carefully selected bars where a guide sets scenes of scandal and rum-running while guests sample the period ambience and a specialty drink.

Suitability

Who it's for

Who this tour suits — and who should skip it.

History buffsIdeal for travelers interested in Prohibition-era Boston and the social history behind illicit nightlife; the guide focuses on stories of rum‑running and political scandal.

Cocktail enthusiastsSuited to those who appreciate craft cocktails in atmospheric settings—guests receive a signature Rum Runner as part of the experience.

Nightlife seekersGood for travelers looking for an evening out that mixes storytelling with intimate bar interiors across three stops.

Families with childrenNot appropriate for minors—participants must be 21 or older with valid ID, so families with young children will need alternative plans.

Practical planner

Details to review before reserving

Timing & Duration

The guided experience lasts approximately 3 hours.

What to Bring

Valid government-issued photo ID is required; participants must be 21 or older.

Meeting & End Points

Tours start in Downtown Boston and end near Faneuil Hall.

Inclusions

The experience includes visits to three historic speakeasies and the opportunity to enjoy the Rum Runner signature cocktail.

Booking Notice

Review cancellation policies before reserving.

Frequently asked questions

Planning Your Outing

How long does the tour last?

The tour runs approximately 3 hours.

Where does the tour start and finish?

Tours start in Downtown Boston and conclude near Faneuil Hall.

Is there an age restriction?

Yes. All participants must be at least 21 years old and present a valid ID; there are no exceptions.

Is a drink included?

Guests enjoy the Rum Runner signature cocktail as part of the experience.

Who operates the tour?

The tour is operated by Rum Runner Speakeasy Tours.