A Boston roadshow day reads simply on paper: eight investor meetings between 8 a.m. and 4 p.m., then a flight. In practice it is a logistics problem with no slack, run across a city whose distances are short but whose minutes are unpredictable.
Having moved deal teams through these days, here is how the ones that run smoothly are actually planned.
One vehicle, one chauffeur, the whole day
The first decision is structural: book the day hourly, as directed — one vehicle and one chauffeur held for the duration — rather than a chain of point-to-point rides. The reasons compound:
- The car is always outside. Meetings end early or run long; an as-directed vehicle absorbs both. A chain of separate bookings absorbs neither.
- The cabin becomes the war room. Between meetings, the team preps the next one in a soundproofed interior with chargers and Wi-Fi — not in a rideshare with a stranger's playlist.
- Materials stay put. Pitch books, luggage for the flight out, the CFO's second suit: loaded once at 7 a.m., touched again at the airport.
Sequencing Boston
The city rewards geographic honesty. Cluster the Financial District and Seaport meetings; treat the river crossing to Kendall Square as its own block, because the bridges are where schedules die; put Back Bay adjacent to whichever block borders it. A sequence that ping-pongs across the Charles will donate forty minutes to traffic that a clustered one keeps.
Rules of thumb that hold up: Financial District to Seaport, minutes; anything to Kendall in the 8–9:30 a.m. window, plan double; the last meeting before a Logan departure should end no closer than 75 minutes to wheels-up for a domestic flight [VERIFY: adjust to current airline check-in guidance].
The buffer discipline
Sophisticated schedulers build two kinds of slack. Micro-buffers: fifteen minutes between meetings absorbs elevator time, security desks, and the handshake that will not end. One macro-buffer: a single 30-minute hole mid-afternoon that the whole day can drain into. Days with no macro-buffer do not recover from a single overrun; days with one usually do.
The airport leg is part of the roadshow
The flight out is a meeting with the strictest chair. Your chauffeur already has the flight number; if it delays, dispatch knows before the team does and the day quietly re-expands. If it doesn't, the vehicle stages so the final meeting ends and the team is on the Pike — or through the tunnel — inside five minutes. See the Logan transfer standard for how tracked departures work.
Multi-vehicle days
Larger syndicates split: principals in one vehicle, support team leapfrogging ahead in another to stage the next room. Central dispatch coordinates both against one itinerary — the kind of arrangement covered under an Enterprise Charter — and the lead chauffeur becomes, in effect, the day's transportation captain.
What to send us
A roadshow booking needs only: the meeting list with addresses and times, traveler names, the outbound flight, and a contact for day-of changes. Dispatch returns a sequenced plan with a fixed all-day quote — no meters running while the car waits, because waiting is the product.
Deansgale runs roadshow days across Boston and Cambridge with a three-hour minimum. Start with a fixed quote at deansgale.com/book.