OK, here is my take (this is long).......
In September of 2002 my wife & I took our h40.5 sailboat to the Chesapeake from our summer mooring in Rhode Island. We spent 4 weeks total on the trip- about 1 week to arrive at the top of the Chesapeake and the last 3 weeks cruising. We wintered our boat with the nice people at Tidewater Marina in Havre 'de Grace.The following spring in April 2003 we cruised for another 2 weeks in the Chesapeake and then made our way back north to Narragansett Bay for the summer season.On both passages, north and south, we motored or motor-sailed nearly all the time. In the fall of 2002 we covered about 750 nm in the 4 weeks that spent, and according to my log we purely sailed only about 50-75nm. The return north was a very similiar experience.This motoring vs sailing scenerio has been apparent to me for as long as I've been sailing on the coasts. Anytime you are constrained by a destination and a time schedule, you are destined to motor except by the very best of luck. Our best sailing days are when we leave our mooring, follow the wind, and arrive whereever.In regard to your 3 week cruise to Block Island, I offer the following-The best and pretty much only stop at the C&D Canal is at Summit North Marina (hole-in-the-wall). You need to pick your day and time in order to catch favorable current toward Delaware Bay very early in the morning.Delaware Bay is one of the nastiest pieces of water I have seen. Plan your passage south in the bay with an ebb current and wind behind you. The top of the bay narrows considerably, and when current and wind are moving toward the top of the bay, all hell breaks loose at the narrowing point. Commercial traffic of ships and tows is frequent.The other problem of Delaware Bay is that there is only one spot to get into before Cape May. That is in the Cohassey River which is about 30nm from Cape May. I have never been there, but it is about a 4nm run from the main channel to a harbor. Being only 30 miles from Cape May, we considered it too short of a day's run, so we went from Cape May to Summit North in one very long day- about 13 hours. You would probably want to stop there since your boat speed will be slightly less than ours.There is a Cape May canal that runs from the Delaware Bay into Cape May. It has a fixed bridge of about 50 or 55 foot clearance. You may be able to get under it, we could not with our 63' mast.Inside Cape May it is very shallow. Check the charts carefully. A marina that has good sailboat access is Utsch's Marina. Call them on the VHF to obtain *exact* entering instructions. It is not obvious, but it is easy. They have diesel and a small convience store.Anchoring is easy in Cape May- choose a spot just north of the Coast Guard Station on the east side of the harbor. Plenty of water and good holding. From there, it is an easy exit to the Atlantic.You next stop up the coast will be Atlantic City (Absecon Inlet). This is a class A inlet and easy to get into. I am told that dock space is available but expensive ($3+/ft). We simply anchored on the south side of the harbor just before the bridge in 17' of water. There is a sand bar that you must go past and then cut left to go behind- check the chart. The current runs swift in the inlet, a good 3kts. We had 0.5kt at our anchor.The next class A inlet up the coast is Manasquan Inlet. It is a long day. I would avoid Barnaget Inlet- it is known to be treacherous and requires local knowledge to pass safely. It should be considered only as an emergency port. Call the Coast Guard if that become a necessity.At Manasquan Inlet you can purchase fuel at several marinas. Some of them are past the bridge, but one is on the left toward the fishing fleet. You have a couple of choices for an overnight stay. Just in front of the cove where the first fuel dock is, a small area with about 5 feet of water exists. There is room for 2-3 boats to anchor. If you continue up the small creek that is there into Willis Hole Basin, you will pass several marinas that may have slips. If you eat dinner at the Wharfside Restaurant, they may let you stay the night at their docks. In Willis Hole, there is room for 1-2 boats to anchor. It is very well protected, but you need to watch your swinging room because the current will flip 180 degrees with tide changes. At one time there was a small work barge moored and I have seen sailboats tied up to it. Another choice is to continue under the bridge on the main inlet and take dock space at one of the marinas up there. I highly recommend the Brielle Yacht Club- very friendly to us the last time we were there. They are on the right, the third marina from the bridge.Your next stop will be either Sandy Hook or you can go up into New York. You can anchor in Gravesend Bay which is on the starboard side nearby Coney Island. It looks like it is pretty open, but we stayed there for 4-5 hours waiting for favorable current in the East River. There is also a marina on the NJ side just north of the Statue of Liberty. It is called Liberty Marina- I've been there back in '89, but I don't know what it is like now.Be sure to hit Hell's Gate at slack current. Plus or minus 20min, no more. Study the charts of the East River to be sure that you can identify all the islands and the correct side of them to be on.After the East River, we anchored in a cove just past the Throgs Neck Bridge on the south side. Easy anchoring, wide open but out of the traffic area. Quiet, nice place to oserve the city skyline. The cove is called Little Bay.Stops to consider in Long Island Sound:Black Rock Harbor near Fairfield, CTDuck Island at Westbrook, CT. Good anchoring behind the breakwaters, fuel easily accessible at the first marina - Pilot Point Marina. Very expensive, $1.89/gal last spring. You are near NYC- be prepared to pay accordingly.Watch Hill, RI: This is a favorite of mine- good anchoring, nice town to visit, decent beach on the ocean. Only 30nm from Block Island.The other places that others have mentioned- 3 mile Harbor:excellent, my kind of place. Montauk: a power-boaters haven, *very expensive, $3/ft for dockage in 1999*, but you can anchor in the pond. The pond is protected but it is a 1.5nm run down into it. Watch the channel, it is well marked but forgives nobody. There is a dog-leg at the beginning of it that regularly snags a sleeping captain. Trust me on this one.As for Block Island- plan on taking a town mooring- they are first-come-first-serve basis. About $35/night in season. Anchoring is very limited in Great Salt Pond. If you arrive on a Mon-Wed you will probably find a good anchoring spot. The worst of the anchoring area is in a 35' deep spot, but most is in 5-10 feet. The island is nice to visit, but is not my favorite place to go. I've had a good dinner at Champlains Marina, but have yet to get a decent meal anywhere else. You do pay like it's a good meal, you just don't get it.You will have a great time. Let me know when you will be at Block, I may be able to come down and met you.Rich