Where pickups start. Annapolis requests most often begin in Downtown / Historic District, Eastport, West Annapolis and Parole. Give the dispatcher a street address or a named lot entrance, not just the neighborhood—drive time, staging, and the vehicle's approach all depend on the exact curb.
Where groups go. Destinations named for Annapolis include Maryland State House, U.S. Naval Academy, City Dock, Rams Head On Stage and Maryland Hall for the Creative Arts. Each has its own loading rules; ask the venue where a bus or limo can wait, and agree on a meeting corner in case the curb is blocked when the group comes out.
Dates that fill first. Local calendars around Annapolis Boat Shows (sailboat & powerboat), Naval Academy Commissioning Week, Maryland Renaissance Festival (nearby) and First Sunday Arts Festival concentrate demand on a handful of weekends. Those dates are worth quoting early; confirm the current schedule with the organizer, since this list is not a live calendar.
Itineraries groups ask about. Downtown Annapolis waterfront bar crawl; Eastport pub loop; BWI Airport to Annapolis hotels; Annapolis to Baltimore shuttle. Share your version with every stop in order and an honest end time so the quote covers the whole block.
Airport groups. Annapolis trips connect to BWI. Provide flight numbers, terminal, bag counts, and one group contact; the driver meets at the commercial-vehicle zone, which is usually not the passenger curb.
Beyond Annapolis. Trips that continue into Baltimore, Bel Air, Bethesda or Bowie are quoted as one itinerary. The Maryland guide covers statewide staging and long-distance planning.