More recommendations
Yes, definitely cross the sound. Do it at its narrowest point if you are concerned. It's really not that wide, and if you keep enough altitude you have a lot of gliding options. The air traffic doesn't get crazy until you get closer to NYC and JFK / LGA. That said, it is well worth a trip down the Hudson River VFR corridor to see the Manhattan skyline from under 1000 feet. If you do this please brief it well. There are clearly defined exit and entry points, and numerous reporting waypoints that everyone uses. Sightseeting helis frequent this corridor, usually at lower altitudes, so use caution.
While in the Boston area you should definitely fly the coast up to Kennebunkport or Portland Maine. If you go that far up I will give you a bunch of tips. If you choose to stay south of Boston, then check these out:
Martha's Vineyard is beautiful and worth exploring at low altitude. There is a very scenic set of grass runways on the southern side of the island called Katama. I found them to be bumpy, by your mileage may vary. There is a restaurant on the field and the field is within walking distance of a spectacular beach.
Chatham on the Cape is another nice stop. You could take a taxi into town and have lunch at a bunch of nice spots, including the pricey but very pretty Chatham Bar Inn. While there, maybe you should fit in a great white shark cruise. The white sharks are back in the Cape in significant numbers, and sightings are on the upswing.
Provincetown on the tip of the cape is worth a stop. The beach is right across from the airport and the dunes are very pretty. If you keep your eyes peeled you may also see whales off the northern coast. I have been fortunate enough to see them feeding a couple of times. A trip into PTown, as the locals call it, is worth it for the restaurants, but don't go if you are easily offended by alternate lifestyles. This isn't a judgement either way, just a statement that there are many overtly sexual themes on signs, shops, restaurants - much like Key West.
The tip of Long Island has Montauk airport. It's a great little spot. I have avoided it during the peak season because I bet it is full of interesting personalities, but in the off season I like to visit a great little seafood restaurant down the road called The Inlet. It offers very fresh and well prepared seafood, as you would expect considering they are down the street from where the commercial fishing boats unload their catch.
I didn't do a ton of flying when I lived outside DC, but if you get a chance the Smithsonian museums are amazing and free. Udvar Hazy at Dulles Airport and the Air & Space in town are musts for any pilot.
Have fun and I hope that helps.
ok.
So fly over the sound.
Block Island and I was thinking of stopping at MVY.
Hudson river.
We're planning on heading to Warshington (as pronounced around here) for a few days then Hotlanta. Perhaps.
Nothing in stone.
Any other recommendations?
Thanks!!