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Old 18-02-2016, 15:27   #1
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Maine to Chesapeake Bay in May

My wife and I will be bringing a "new to us" boat down from Maine to the Chesapeake Bay starting around May 1st of this year. We are long time sailors but have not sailed in the NorthEast US before and were wondering if any of you NE sailors had suggestions for stops along the way.
We are coming back this way late summer or next year but will have some friends with us this trip and would like to see some of the highlight anchorages/moorings. If we can stay out of the marina we would like to but if needed we can stay anywhere.
We are 50 ft and draft 6 ft.
We would like to be back in the Bay in about a month, weather permitting, but we can just do a long delivery type sail if we have too much to see in the north and are running behind.
Let me know your suggestions for your perfect trip south from southern Maine.
Thanks,

Jim
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Old 18-02-2016, 15:58   #2
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Re: Maine to Chesapeake Bay in May

Quote:
Originally Posted by jkleins View Post
My wife and I will be bringing a "new to us" boat down from Maine to the Chesapeake Bay starting around May 1st of this year. We are long time sailors but have not sailed in the NorthEast US before and were wondering if any of you NE sailors had suggestions for stops along the way.
We are coming back this way late summer or next year but will have some friends with us this trip and would like to see some of the highlight anchorages/moorings. If we can stay out of the marina we would like to but if needed we can stay anywhere.
We are 50 ft and draft 6 ft.
We would like to be back in the Bay in about a month, weather permitting, but we can just do a long delivery type sail if we have too much to see in the north and are running behind.
Let me know your suggestions for your perfect trip south from southern Maine.
Thanks,

Jim
Congrats on your new boat. You have plenty options depending on your interests and time table. It is fun and relaxing go inside LI sound and thru NYC harbor. Drop anchor in Sandy Hook, NJ and wait for weather window to Cape May. From there to C&D Canal. I don't care much about stopping between Sandy Hook and Cape may, but that is just me.

Of course, you can easily jump from Block to Cape May or Norfolk

I am sure you have Active captain in your smart phone. It is the best for the up-to-date local knowledge.

Good luck !!!
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Old 18-02-2016, 16:37   #3
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Re: Maine to Chesapeake Bay in May

Sailed due south out of Camden ME to DR a few years back, was first week of May. Was very cold especially at night for a good 3 to 5 days, probably 500 miles south of Maine it warmed up enough to stop shivering.
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Old 19-02-2016, 06:22   #4
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Re: Maine to Chesapeake Bay in May

Larry is right. When we put our boat in during May and even early June we put all of our winter jackets, hats and mitten aboard because the Gulf of Maine waters are still in the forties and the wind cuts through to you.

My advise is to wait a month before starting. You will have a nicer trip.

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Old 19-02-2016, 07:19   #5
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Re: Maine to Chesapeake Bay in May

Yes I realize it is early but June is very nice in the Chesapeake as well and we live in this area right now. We bought the boat in the fall and decided to get some work done over the winter and have not been out on it since October. I know you guys are used to that up north but I am ready to get it in the water. It is a pilot house motorsailer so we should be able to get out of the weather a little.

I was looking for some stops between Harpswell and the Boston area that we could stop at on the way down. Just overnight anchorages or "wait for weather stops". Does anyone have any favorites on that route?
Also we were thinking hitting Nantucket and /or Martha's Vineyard along the way and then the Bay's to the north just because we have heard about them. Is it too early for things to be open? Anything on the Long Island north shore we might like?

Jim
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Old 19-02-2016, 07:25   #6
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Re: Maine to Chesapeake Bay in May

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Originally Posted by rockDAWG View Post
Congrats on your new boat. You have plenty options depending on your interests and time table. It is fun and relaxing go inside LI sound and thru NYC harbor. Drop anchor in Sandy Hook, NJ and wait for weather window to Cape May. From there to C&D Canal. I don't care much about stopping between Sandy Hook and Cape may, but that is just me.

Of course, you can easily jump from Block to Cape May or Norfolk

I am sure you have Active captain in your smart phone. It is the best for the up-to-date local knowledge.

Good luck !!!
The inside route looked interesting but a little more intimidating from a traffic standpoint being our first time in the area. We did go through the Panama Canal though so we shouldn't be worried but we always feel better away from land for some reason. There seems to be less things to hit.
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Old 19-02-2016, 08:27   #7
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Re: Maine to Chesapeake Bay in May

+1 on congrats on the new boat and dress warmly. May is late nor'easter time in New England. Snow is unlikely, but air temps in the 40's are common.

From Harpswell, I would jump down to MA. P'town is very protected and a jumping off for the next leg. Gloucester and Marblehead/Salem are good options if you're interested in exploring Massachusetts and considering heading to Boston. If you want a shorter first leg, Isles of Shoals is a good stop, but I would want to confirm that their moorings are in. Holding is supposed to be very difficult. I haven't tried anchoring there for that reason.

If you want to go to Nantucket and Martha's Vineyard, your more direct route is around the East side of Cape Cod. However, you'll want to do that with a secure weather window and good radar. It's a lee shore in a nor'easter with no safe harbors with your draft. The Pollock Rip channel between Monomoy and Nantucket is doable, but it's not fun in fog or weather.

A safer route is through the Cape Cod Canal. Get a copy of Eldredge's and schedule your transit with a favorable current and, ideally, little wind at the Buzzard's Bay end. It's easy to leave from P'town, Scituate on the mainland (also a nice stopping point), or Sandwich harbor at the East end of the canal. Be aware that if you exit into Buzzard's Bay into an afternoon sou'wester, the chop caused by the wind and current against each other will loosen any sludge in your diesel tank. (Don't ask me how I know that.)

Buzzard's Bay has lots of nice places to stop. You'll be very early in the season so won't have to worry about crowds. Hadley's Harbor on the SW side of the entrance to Wood's Hole and Cuttyhunk are great at that time of year. Don't anchor outside C'hunk in a northerly.

If you decide you have time for Martha's Vineyard or Nantucket, go through Wood's Hole and you're well positioned for both, but heading away from your rhumb line to Chessie. If you decide to pass on them this trip, Cutty to Great Pond on Block Island is an easy leg. I'm partial to Narragansett Bay which is a quick detour. Newport will just be waking up and is very easy access and a good place to fix things you discovered on your shakedown from Harpswell.

Block Island is a great jump off for the outside route as is Shelter Island and a number of nice spots in Gardiner's Bay at the eastern end of Long Island. Further south I'll leave to others.

Enjoy the trip, but bring clothes appropriate for skiing.
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Old 19-02-2016, 08:41   #8
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Re: Maine to Chesapeake Bay in May

We purchased our Pearson 31 in Harpswell a few years back and sailed her down to Massachusetts in late April. Very cold!

Our first stop (unplanned due to weather) was Kennebunkport. Pretty town free, overnight dockage because it was preseason, but needed a high tide.

But the easy in and easy out harbors north of the cape cod canal where you can easily grab a mooring would be Gloucester, MA; Marblehead/Salem, MA; Ipswich, MA.
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Old 19-02-2016, 08:57   #9
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Re: Maine to Chesapeake Bay in May

No one mentioned Portsmouth or Rye Harbor, NH. I believe I'd prefer those over Isle of Shoals, though more time consuming in and out. Excellent dining and touristy type stuff in Portsmouth within an easy walk from the dock at Prescott Park. At $50 overnight for a fifty footer, it's pricey but worth it IMO.

<http://www.cityofportsmouth.com/prescottpark/docks.htm>

Or if you want a real upscale experience, right around the corner is New Castle's Wentworth Hotel, Spa and Marina.

In either case I would try to time the arrival to coincide with flood tide, as the Piscataqua River current is too fast for most sailing vessels to overcome at maximum ebb. I once watched a captain with his holiday crew actually backing up at full throttle trying to head down river during peak flood tide. Funny to us onlookers but embarrassing, I'm sure, for him.

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Old 19-02-2016, 09:16   #10
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Re: Maine to Chesapeake Bay in May

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Enjoy the trip, but bring clothes appropriate for skiing.
This was the admiral when we brought our boat from Salem, MA to Bristol, RI in mid-May. Temp in the low 40's. NE winds 15-30, spitting rain.

As someone once said, there is no such thing as bad weather, just unsuitable clothing. We have a diesel heater. Amazing how many reasons were found to spend time below.
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Old 19-02-2016, 09:21   #11
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Re: Maine to Chesapeake Bay in May

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We purchased our Pearson 31 in Harpswell a few years back and sailed her down to Massachusetts in late April. Very cold!

Our first stop (unplanned due to weather) was Kennebunkport. Pretty town free, overnight dockage because it was preseason, but needed a high tide.

But the easy in and easy out harbors north of the cape cod canal where you can easily grab a mooring would be Gloucester, MA; Marblehead/Salem, MA; Ipswich, MA.
Edit: I meant to say Scituate, Ma not Ipswich.
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Old 19-02-2016, 09:59   #12
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Re: Maine to Chesapeake Bay in May

Some of my favorite spots - north Shore of Long Island - east to west

Orient Point: very quaint, very pre-Revolutionary, very pretty. Boat friendly.
Greenport: Recreational boating and lobstermen side by side. Chandleries are
Prestons, right at the dock and I alway used White's Hardware, less
expensive.
Mattituck: A long approach along the inlet but 2 boatyards and some restaurants
when you get there.
Mt. Sinai: Lots of parking for your boat but no restaurants. Old Man's Boatyard
for fuel and repairs. No chandlery.
Pt. Jefferson: Major village. Boatyards, yacht clubs, restaurants, shopping,
trains to NYC, etc.
Northport/Huntington: Now you're getting close to the city. Lots of "shoppes"
boat parts, transport. All associated costs are going way up now.
Pt. Washington: Huge boating tradition. Although expensive compared to further
east, probably the best stop before going through the rivers and
NY City.

Equally, you could hug the CT south shore, but I don't know as much about it.

in Manhattan there's the 79th St. Boat Basin which is a lot of fun and the Liberty
Marina in NJ which is just a ferry ride across to the city.

Lots to do, lots to see! Enjoy it if you choose this route.
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Old 19-02-2016, 11:32   #13
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Re: Maine to Chesapeake Bay in May

First off, we did part of the reverse of that (Connecticut to Maine) in April to bring our boat home. I think we had to brush off a dusting of snow before starting one day.

If you plan to stay at marinas, be aware that many don't start their season until May 15th or so. On the other hand, you should ask for off-season rates. Since they're not expecting any transients anyway, they may just say OK and give you a great deal.

As to the Isles of Shoals recommendation, be aware that many of the moorings in Gosport Harbor are pulled for the winter, and those that remain have endured the brunt of several really good winter storms. I wouldn't trust any of them this time of year. On the other hand, anchoring on the East side of the breakwater in the lee of Smuttynose Island would be a pretty good in anything with a northerly or westerly component.
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Old 19-02-2016, 11:38   #14
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Re: Maine to Chesapeake Bay in May

We're based in Belfast, ME and have made the trip many times. It is very cold in May but a pilothouse makes it much better. We have often used a mooring in Boston- $50/night for a 50' boat and right off the Aquarium and Quincy Market. Right after a frontal passage the wind is usually westerly for 2-3 days and makes the passage from Maine to the CC canal a fast reach.

There are enough Nor'easters and Easterly winds in May to make the CC canal-Buzzard's Bay- RI Sound- LI Sound- NYC a more comfortable choice.
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Old 19-02-2016, 12:39   #15
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Re: Maine to Chesapeake Bay in May

All the information is spot on, only add I would have is; skip Nantucket and MV, stop and Cutty, Newport (nicer earlier in the season) Block.
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