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Agree with the advice about backing off a little. Cape May to MV is an overreach IMHO. You need to allow for bad weather and losing a few travel days. Hopefully you can be in an interesting harbor while you wait for better conditions.

In our local area, Mystic, Fishers Island (East and West Harbors), Stonington, Watch Hill (anchorage just outside the inner harbor called Napatree locally) are good stops. Fishers Island shoreside facilities are minimal (non-existent at East Harbor), but the others are reasonable for a visit or a layover. Further East are Block Island and Point Judith (Harbor of Refuge and salt pond) and even further east is Newport--a sailors' destination if ever there was one.

I have been sailing out of Mystic for over 40 years and I never venture out without checking with Eldridge's Tide and Pilot Book. You really want to time transits with the currents. Suggest you check page 85 of the 2014 Eldridges and familiarize yourself with the information on LIS (including Block Island) on pages 86-89. If you make it further east, there is a section on Buzzard's Bay and MV (pages 60-77). Eldridge's also has info on Sandy Hook, Delaware Bay, C&D canal, etc.

If you make it to Mystic, there is a small anchorage east of Mystic Shipyard (south of the RR bridge) that will just barely accommodate your draft (board up) and another immediately north of Mystic Seaport, just past the last channel buoy. There are dinghy docks by the Rt 1 drawbridge and at Holmes St (east side, just past Schooner Wharf). Both are in the middle of Mystic and an easy walk to Mystic Seaport, which may also accommodate your dinghy when you pay admission. Dockage at Mystic Seaport is expensive--on the order of $4.50/ft, but includes admission for all aboard, which otherwise would cost you $78 for 2 adults and 2 kids (6-17). The Seaport has restrooms/showers/laundromat/pumpout, etc. Check their website: Mystic Seaport Marina | Mystic Seaport.

 

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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.

Tempest has some good advice, but you'll need to plan on a 3 day transit from Cape May to Vineyard Haven, if conditions allow. Block Island could be a 2-day passage: you wouldn't save much time to divert to Lake Montauk over continuing to Block. You'll be crossing the New York shipping lanes and will need to deal with crossing paths at night with larger vessels. With only 2 watch standers that are new at this, you might find yourselves sleep-deprived by the second day.

You also want to consider this an ocean passage with the distinct possibility of sea sickness for all aboard.

However you get to MV, you might consider anchoring in Lake Tashmoo (there also may be moorings available from a small marina there, but not sure.) Lake Tashmoo has a town dock with water and trash pickup and is a 1.25 mile walk into Vineyard Haven. You'll need to mind the chart entering, but you will sleep better here than in Vineyard Haven, which has a lot of boat traffic (wakes) and is more open--especially when the weather turns foul.

 

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FYI, T37: On my delivery trip from Clearwater, FL to Mystic in 1996, we stopped in Annapolis and continued via the C&D and Cape May canals. Conditions were such that we motored almost all of this segment, with the sails up for only 5 hours. So, if you find yourself motoring, here are some numbers for my 35' sloop for your consideration.

Annapolis YC to 2nd bend,Cohansey River (SW NJ): 81 nm, 14:45 hours--motoring at 2200 rpm.

Cohansey River, past Montauk, to East Harbor, Fishers Island, NY. (This is comparable to sailing to the salt pond at Block Island): 235 nm, 42 hours--motoring the whole way, with only a slight boost from motor sailing for a 5 hr period--2200 rpm. (N.B. our fuel stop at Utsch's in Cape May only took a half hour.) With this amount of motoring, we transferred 6 gal of diesel from a jerry jug at sea under calm conditions. You want to have a healthy fuel reserve, just in case.

Note our rather conservative engine speed. We were in a sweet spot for fuel consumption, averaging >10 nm/g in relative calm conditions (for the open ocean.) If you have to motor into seas/wind, or need to increase your speed over ground, you can expect dramatically worse mpg figures. We were motoring at just under hull speed and were not towing a dinghy.

 

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I will fill in Cape May (50 gallon tank on our boat using about .5 gallons an hour at 5.5 knots) plus at least two Jerry cans = 60 gallons total. Conservatively that 100+ hours of motoring if needed. Shouldn't that be sufficient?

Your 50 gallon tank is perfectly adequate for this trip, without extra jerry jugs, assuming you are starting from Cape May with a full tank. I motored from Cape May all the way to Fishers Island Sound (equivalent to motoring to Block Island) on less than 20 gallons under calm conditions. (Otherwise I would have been sailing--the 5 hours of motor sailing didn't provide a significant boost on that leg.)

I transferred about 5.5 gallons at sea to maintain a reserve, but the conditions were benign. I wouldn't want to transfer fuel when it gets nasty.

One of the lessons we confirmed on my 1500 nm delivery trip from Clearwater, FL, to Mystic was that the weather doesn't always accommodate your plans. We headed in when the weather looked adverse and motored when the sailing conditions were lame. We left the boat in Stuart, FL, for about 10 days, and took lay days in Beaufort, NC, and Annapolis for crew rest. BTW, we only used 50 gallons of diesel for the whole trip. If you can't make it from Cape May to MV on 50 gallons, you are doing something terribly wrong.

 

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Zodiac beach...swimming with the sharks

Actually, the locals usually refer to it as "Dinghy Beach", so as not to play favorites. Besides there are all sorts of other brands there.

Not saying there aren't sharks at Scotch Beach, but after sailing in this area for over 30 years, the nearest I've seen a great white is about a mile off Block Island. You are more likely to see striped bass near the beach. For that reason, you might consider snorkeling in water deeper than about 4 ft and looking for what you folks from the Chesapeake call rockfish.

FWIW, last July we saw several harbor seals at the extreme northern tip of the island, within 50 feet of the shore. Since the great whites in New England waters are known to feed on seals, maybe we have been swimming with the sharks and didn't know it. Hmmm!

 

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BTW, Scotch Beach is the ocean beach a short walk from Dinghy Beach, which is on the salt pond.