Brooklyn Bridge plus DUMBO or Brooklyn Heights or Lower Manhattan
Disclaimer: the Brooklyn Bridge can be very crowded, especially in the busy season (as long as it's not off hours). It may not be "worth it" to have a tour guide with you, especially if you're a large group.
Enjoy stunning views of the Manhattan and Brooklyn skyline; discover the adjacent waterfront neighborhoods in Brooklyn.
Most tours of the Brooklyn Bridge start in Manhattan and end in Brooklyn. I can and do lead such tours, starting at various points in Lower Manhattan (like Wall Street or City Hall Park), then proceeding to DUMBO, Fulton Ferry, and Brooklyn Heights.
However, as a Brooklyn-centric tour guide, I also recommend doing the opposite: start on the Brooklyn side. We'd start with a good walk through downtown Brooklyn and Brooklyn Heights, the city’s first landmarked neighborhood. Or we can start instead in DUMBO, which is closer to the bridge, and gives us a look at Brooklyn Bridge Park and Fulton Ferry. Or we can do both.
As we walk over the bridge, we get great views of the harbor and a chance to learn the bridge’s complicated, glorious history, the innovations behind it, and the family that oversaw it (and died/suffered during construction). Today, the Brooklyn Bridge remains a marvel and an icon, albeit one that requires ongoing repair. (Alternative: skip the bridge; take the ferry.)
We can end just over the bridge at City Hall Park, where there are many subway options, or we (or you) can walk around Lower Manhattan, including to Wall Street/Financial District, and ultimately to Ground Zero.
For those new to Brooklyn, please note this tour focuses only on a small piece of Brooklyn. For a more extensive introduction, I recommend the Brooklyn 101 tour, with the bridge as an add-on.
Distance from Midtown Manhattan: 20-25 minutes by subway
Basic tour length: 2-2.5 hours (see fees)
Starting place: Varies, possibly Borough Hall, Brooklyn. (Or do it " backwards.")
Ending place: Varies, possibly City Hall, Manhattan. (Or do it " backwards.")
Alternative: Skip the bridge, take the NYC Ferry from Fulton Ferry in Brooklyn to Pier 11 in Lower Manhattan
Highlights: History, architecture, waterfront views, parks
Before tour: Visit the Transit Museum in Brooklyn
After tour: You're in Manhattan, near the City Hall subway station.
Potential tour extensions with me: Brooklyn 101, Atlantic Avenue