Chesapeake to Nantucket cruise plan

[Delta sailor]

I have a small family, wife and 2 boys and we own a 38' boat docked in MD. Looking to take 1 month next summer and cruise north. Wondering what would be recommended. New York, Martha's vineyard, go up to cape cod, etc.? And what about timelines for different legs. Planning on next spring
We're staying in the bay this year. TIA

[psk125]

Sounds like a great idea. Take your time so that bad weather doesn’t catch you out. NYC is really expensive, but quite cool. (Liberty Landing Marina?) Lots to see & do all the way to Nantucket. Get the Embassy Cruising Guide(s) for the trip and look through them to find things that interest you. History? Art? Food? Submarines? Architecture? Fishing? Every harbor has something different to offer. You could take two months, maybe three, and still not be finished.

[TheOffice]

With kids I would go up the East River through NY. Very cool! Stop in Mystic at the Seaport, Newport, Cuttyhunk.

[stepbnd]

My wife, daughter and I just did a similar trip. We were a bit pressed for time so we pretty much skipped everything from Annapolis to NYC. Left Annapolis on a Saturday morning, anchored in Delaware bay that night, and sailed into NYC mid morning on Monday.
Here are my suggestions:

Anchor one night behind the Statue of Liberty. It can be fairly rough, but the views make up for it. Especially the Manhattan skyline at night.

If you're on a budget, check out the mooring balls at the 79th Street Boat Basin on the Hudson River. $30 per night. The Hudson was pretty rough most of the time we were there and the docks at the marina are in terrible shape, but the location is hard to beat. 2 block walk up to Broadway.

East River through Hell's Gate is awesome, but you absolutely have to time the currents.

Port Washington is a cool next stop and has mooring balls for transients that are free for 48 hours.

We unfortunately skipped Block Island, Martha's Vineyard, and Nantucket and went directly to Cape Cod - basically due to time constraints, so I can't offer anything on those areas.

[bensolomon]

Just took my boat from Rock Hall to mystic, CT. Then Newport and block. Went outside.

Rock Hall to Bohemia River and anchored. Bohemia to Cape May, and got a slip at Canyon club. Enjoy cape may for a day or two. Due to severe weather, went from cape may to Atlantic City. Had a great dinner and tied up at Atlantic City municipal marina. Big party spot.

From AC, overnight directly to Mystic, at Brewers yacht yard, now Safe harbor marina. From mystic, did Block and Newport. Plan then to go to cuttyhunk and lay over then to the vineyard.

I would have gone to Montauk instead of mystic (was actually the plan) but lost a day due to weather (the Atlantic City stopover).

I have a wife and three kids who do not love sailing, but they enjoy a four to six hour sail. The way I sail is a compromise ( the land stops). Limiting the trip to one overnight is important for family sanity.

Also, I picked brewer's in mystic because it is walking distance to the train station and rental bikes, and mystic downtown is adorable.

I have also gone "inside to NYC. I prefer the outside passage. Outside you could go right to block, or Newport should the wind and current be favorable.

Get an Eldridge so you can time the C&D canal transit and entering Long Island sound, and the race as well as entering block island. Favorable current is key.

Last thing....DO NOT enter Long island sound in the dark (no foreign harbor at night) unless you have prior knowledge of the area. Specifically, Lord's passage to Napatree, and Watch hill. Hazards abound!

I also recommend using WRI for routing advice with the weather. That will help you pick your timing.

Ben