BOSTON GUIDED TOUR FIELD GUIDE
Boston After Dark: The Big Shot Private Speakeasy Tour for 5–8 Guests
An intimate, three-hour private walkthrough of Boston’s hidden speakeasy scenes — this guide explains what to expect, who it’s best for, and the logistics to plan.
Boston After Dark: The Big Shot Private Speakeasy Tour for 5–8 Guests.
Gather 5–8 friends for an exclusive, private look into Boston’s clandestine bar culture: a guided, three-hour experience that moves from downtown through evocative speakeasy atmospheres and concludes near Faneuil Hall. It’s built for small celebrations and groups who want the guide — and the stories — all to themselves.
Highlights
Outing Highlights
Hidden Speakeasy Ambience
Step into low-lit rooms and intimate bars that recreate the hush-and-hush feel of Prohibition-era hideouts; the tour emphasizes the mood and design that make each stop feel like a secret.
Scandalous Local Stories
The route threads scandalous local history through its stops, giving context to the speakeasy scenes and the characters who populated them.
Private, Intimate Groups
Designed specifically for parties of 5–8, the outing keeps the group small and private — a format tailored to celebrations, bachelor/bachelorette nights, and close-knit friend groups.
What the day feels like
What the evening feels like
Over roughly three hours you move with a single guide through downtown corridors into tucked-away bars, hearing scandal-rich vignettes and absorbing atmospheres that feel removed from the bustle outside — all with the privacy and focus of a small, reserved group.
Suitability
Who it's for
Who this private tour suits — and who it doesn’t.
Practical planner
Details to review before reserving
The private tour runs approximately 3 hours.
Valid photo ID is required for all participants (21+ only).
Tours start in Downtown and end near Faneuil Hall; plan your arrival and post-tour plans around those areas.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the private tour?
The experience lasts approximately 3 hours.
How many people can join a private booking?
Private bookings are for groups of 5–8 guests.
Is there an age requirement?
Yes — all participants must be 21 or older and present valid ID; there are no exceptions.
Where does the tour meet and end?
Tours begin in Downtown and conclude near Faneuil Hall.
Is the experience truly private?
Yes — the 'Big Shot' is a private experience reserved for your party of 5–8 guests with a dedicated guide.
Who operates the tour?
The tour is operated by Rum Runner Speakeasy Tours.
Is there a group discount for private bookings?
Private bookings for the Big Shot are offered with a booking discount for 5–8 guests.