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You'll probably want to make a reservation in Cape May if you want a slip for the night.
I believe Utsche's marina has the best price @ 2.00/ft. South Jersey Marina is a dollar more ($2.95) But double check. Don't wander out of the channel on the east side exiting the canal. The currents can run pretty good around the channels and marinas

If the current is favorable, I've left the C&D canal in the wee hours of the morning ( 2 a.m. once) headed for Cape May in order to beat the heat and green head flys that can terrorize you on the bay.

Options for stops are endless once out toward MV and Block. Block has become a real PIA in the summer, but if you haven't done it, it's an experience. I feel most comfortable on a town mooring,(green balls) or, a private mooring obtained through calling the harbormaster on VHF by 3 p.m. The anchorage can get very crowded, the slips @ Champlin's are expensive and you are rafted up at the dock sometimes 4 across.

On the LI sound coming back..Lots of stops...I tend to like the Connecticut River area..Old Saybrook, north cove, or Essex then I cross over to Port Jefferson. Some like to stay on the Connecticut side. From PJ you can head straight for NY or the highlands in a long day..or stop at Port Washington or City Island. and try to catch a morning ride down the east river. Diesel fuel, if needed, is easier to obtain in Manhasset bay than on City Island. Have a great Trip.. keep us posted.
 

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Shawn, if the prevailing southwest wind is in place the sail to block gets you up there faster...from Cape May.

That same SW wind makes coming home offshore potentially a close hauled trip back.

Coming back inside the LIS gives you some nice places to stop on the way home like NYC ( on your list) being one. The downside to inside is you'll probably end end up motor sailing a fair bit of the way. My experience in the summers coming home on the sound..is that the winds typically don't pick up until afternoon, not unlike the Bay. So leaving port at 7 am..on the next leg will usually have you motoring sailing until noon or so. My strategy is to catch fish..and jump in for a swim..once in awhile. You could hang around town in the mornings, and leave when the wind picks up...and arrive at your next stop later. There's often an evening thunderstorm to dodge in July.

I tend to get up and go..and make coffee underway.
 

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Chef, IF the Vineyard is going to remain your main objective, ( which seems to be the case ) IF the weather cooperates and IF the crew? is up for it ? you could try to bite the bullet and sail directly there from Cape May. I think this is a big sail for your 1st trip out of the Chesapeake, with only 2 ? at the helm. You both have to be able to get sleep. Getting into a regular rest routine is toughest the 1st 36 hours, but you really have to commit to sleep/rest times to remain fresh.

You'll also need a decent 40 + hour forecast to accomplish this. You will know after the 1st 24 hours from Cape May how you are doing. You can always decide to divert a few degrees west and head for Block Island once you're out there. IF you're able to get to MV 1st, then you can visit with your friend and head for Block. ( this cuts out the double trip from Block to MV and MV back to block or cuttyhunk). Once on Block, (56 miles from MV) you can decide if you want to attempt the return trip outside or take the inside trip home. Again, you'll need to ascertain the weather for the trip outside, which is generally against the prevailing winds and seas. You'll want to time your landfalls in daylight, so I would let my desired arrival time determine the departure time from Cape May or points beyond.

I was scheduled to do this trip last year and the weather was not very cooperative outside, with one low after the other marching straight up the coast held near shore by a stationary high offshore producing 9 ft seas at times. You're really going to have to be flexible and take what the weather gods give you. You could literally get to Cape May or somewhere..and be stuck for a few days.or have to divert, and make a new plan. It happens.

Eldridge really is your bible for these waters (and a good weather window). Despite our best plans, Wind, Weather, Current, is really going to dictate how far you get and which route is best. I hope you do get a favorable window. Remember it's a Vacation.
 

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Shawn, It was Great to meet you and I'm Glad I could help out. I sent you a text. looks like you can sleep in a little tomorrow morning as the east river current turns in your favor in the afternoon.

Make sure the camera is out. Enjoy the rest of the journey. Maybe we'll catch up on your return trip. Fair Winds!
 

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AC will be a long Day but I think that's a good call. It will give you a shorter sail the next day to Cape May and allow you to spend more time in a great beach town.
The morning might still be a little wet and bumpy though mostly swell. But if the West and NW winds show up as expected you should be able to sail the whole coast over the next few days. We look forward to the Return of SV Windgeist to this neck of the woods.
Have a great trip home.
 
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