Sorry - realize something is not clear above - we do not want GW Bridge - and that is way GPS/Mapquest always wants us to go. We know what to do after crossing Tappan Zee Bridge

Two ways: most fun is for her to go to Lewes, DE, and take the car ferry to Cape May, NJ. From there it is a straight shot up the GSP to 287 and the Tappan Zee Bridge.

The second way is to cross the bridge to the Eastern Shore and take 301 to I-95 between Newark (DE) and Wilmington. Then it's up the NJT to the GSP at Woodbridge and as above.

She should plan to buy gas at Montvale, the last rest area in Jersey, because it is vastly more expensive in New York State and Connecticut, though it gets slightly better as you drive beyond Fairfield County.

I assume that you will have her drive up the Merritt Parkway and Wilbur Cross Parkways in Connecticut. They connect to I-91 south of Hartford, and it is an easy connection to I-84 and the MassPike. This is much faster, easier, and more pleasant (EXCEPT at rush hour) tha I-95 for any place north of Dedham.

Just did most of this last week, so it is fresh on my mind.

On maps.google.com, if the software gives you a route through the GW Bridge, you can literally drag the route shown to cross at the Tappan Zee. Then it recalculates, draws a new route, and provides written directions. Mapquest may do the same.

Thanks - did not know about the dragging thing on google.

Sometimes we take Merritt Prkwy and sometimes 684 to 84 to MassPike. Avoid 95 like the plague

The exit off of the NJ Turnpike where it intersects the Garden State Parkway is Exit 11 on the NJT. Signs will say Exit 11-GSP/Woodbridge. Once thru the toll, follow signs for the Garden State Pkwy North.
There is a convenient rest stop just before the end of the GSP...the entrance to the rest stop will be on the left. At the end of the GSP, bear right to merge onto 287E/87S towards the Tappan Zee Bridge (follow signs for 87S). After you go over the Tappan Zee Bridge, there are two routes to choose from, close in mileage and time, just different.

Option 1: Once over the Tappan Zee Bridge, stay to the left and head towards White Plains/New England. Take Exit 9N (Hutchinson River Pkwy/Merritt Pkwy - different names depending on whether you're in NY or CT - same road). Follow signs to 15N (toward CT) - hint: stay in the left lane when you get off Exit 9N; there is a light; you'll continue straight and then after the light, move to the right lane to get onto the ramp for 15N. Take the Merritt Parkway (Rt. 15)to 91N. Follow 91N to 84N towards Hartford/Boston. Follow 84 to 90E. (Advantages to this route: Merritt Pkwy is a beautiful (but winding drive). No trucks allowed. Small rest areas along route. Disadvantages: Limited amenities off exits unless you are familiar with the towns. Need to drive carefully due to sharp curves and/or bad weather; merging traffic. Need to watch signs for switches between routes.)

Option 2: Same directions to/over the Tappan Zee Bridge. After crossing the bridge, stay left, heading towards White Plains/New England.
Take exit 9A and merge onto I-684N (towards Brewster). After approx. 28 miles, take Exit 9E to merge onto I-84E toward Danbury/Newburgh. You'll be on 84 for approx. 100 miles. Follow signs for I-90E (NH/Maine/Boston). Merge onto I-90E, which will take you close to Boston.
Advantages: Less switching between routes. Larger rest areas. Good roads/more visible amenities off exits.
Disadvantages: 10 miles longer. Not as pretty as Merritt Parkway, but still nice sections. More traffic than the Merritt, including trucks. (But Merritt is small portion of entire trip.)

Sorry for the length, but hope it helps. We live in CT and travel often to Baltimore and back and also to the New England coast. We've done both routes; both work nicely. Good luck and safe travels!

As a former CT resident now in Baltimore, the 684/I84E trip can have many delays in Brewster/Danbury, Waterbury and Hartford - especially on a Friday. As much as I hate the southern route (Merritt and I91 and or I95 options) at least there are on highway rest areas.

From Annapolis she could (unless she is in some great big hurry) take Rte 50 East across the Chesapeake Bay Bridge and then take 301 North. It is a much more relaxed drive than the Maryland portion of I-95 and the speed limit is also lower. Four lanes until she crosses into delaware at Middletown and then take Del Rte 896 North to I-95