Cape Cod and Surrounding Area – Points of Interest

Alex F

Well-Known Member
Nov 14, 2006
9,166
Miami / Ft Lauderdale
Boat Info
2005 420DB with AB 11 DLX Tender, Raymarine Electronics (2x12" MFDs) with Vesper AIS
Engines
Cummins 450Cs, 9KW Onan Generator, 40HP Yamaha for tender.
Last year we made the trip to MV and Nantucket islands. We didn’t have enough time to explore Elizabeth islands, but it’s on the radar for this season. While there I was planning to head further north and explore Cape Cod area.

I found few things while searching CSR and reading cruising guides, but I would appreciate recommendations and local knowledge about interesting places (ports, harbors, anchorages, beaches, etc.) that we shouldn’t overlook. If anyone also has suggestions on good restaurants that would be great.

Thanks,
Alex.
 
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Wetpaint (aka Kewlchange, aka John) is your man with local knowledge. That is where he kept his 36DB and I believe his new cat is there too. He was kind enough to give me some tips when my wife and I visited there in 2011.
 
Thanks Robert,

I hope John has wifi in Caribbeans and seas this thread. John gave me great tips on the MV trip, but we also have other members from the area that I'd love to hear from.
 
In the Elizabeth Islands you should check out Cuttyhunk but there is only one small restaurant and it may not be open all the time. But one of the islanders will take orders for steamed lobsters and bring it to your boat. Also at the North end of the EI's you should stop overnight in Hadley's Harbor with free moorings compliments of the Forbes family that own the EI's. Beautiful spot to relax and swim. If you want something unusual go thru the CC Canal and across CC Bay to Provincetown for 2-3 nights. More good restaurants than you can count, but for breakfast go to the Portugese bakery. Trust me you'll be talking about it for a long time.
 
In the Elizabeth Islands you should check out Cuttyhunk but there is only one small restaurant and it may not be open all the time. But one of the islanders will take orders for steamed lobsters and bring it to your boat.

I was planning to do Cuttyhunk last year but instead we stayed extra days in Edgartown. I'm looking at Cuttyhunk as my first stop in EIs this time around.

Also at the North end of the EI's you should stop overnight in Hadley's Harbor with free moorings compliments of the Forbes family that own the EI's. Beautiful spot to relax and swim.

That's perfect, excatly what I was looking for. In the cruising guide Woods Hole looked like a good spot, but I'll definitelly look closer in to your suggestion on Hadley's Harbor.


If you want something unusual go thru the CC Canal and across CC Bay to Provincetown for 2-3 nights. More good restaurants than you can count, but for breakfast go to the Portugese bakery. Trust me you'll be talking about it for a long time.

...LOL.....Thanks. P-town is on my must have stops.

Based on my preliminary findings I have the following ports/stops as candidates to my itinerary:

Cape Cod:
--------------
Provincetown
Plymouth
Chatham
Monomoy Island
Gloucester - not sure if I'm going so much north this time, though.

Elizabeth Islands:
------------------
Cuttyhunk
Hadley Harbor
Woods Hole
Quicks Hole
Tarpauline Cove

If you have any comments on any of these places I would appreciate it.
 
Alex, these are all good choices, with some qualification: I would consider Quicks Hole and Tarpauline Cove to be lunch/swim stops only. They might qualify for overnight anchorage in certain wind conditions, but are exposed and can get rough.

Given that itinerary, I would not bother to go all the way up to Gloucester which I do not consider to be a destination in and of itself, more of a stopover on our way to Maine. If you have time, Boston Harbor and its islands are nice, as is Marblehead and Salem.

i can't remember offhand the ages of your kids, but Provincetown may require some explaining. It's loads of fun and we love going there, and I think it helped my kids gain an understanding of gays and lesbians.
 
Alex, these are all good choices, with some qualification: I would consider Quicks Hole and Tarpauline Cove to be lunch/swim stops only. They might qualify for overnight anchorage in certain wind conditions, but are exposed and can get rough.

Given that itinerary, I would not bother to go all the way up to Gloucester which I do not consider to be a destination in and of itself, more of a stopover on our way to Maine. If you have time, Boston Harbor and its islands are nice, as is Marblehead and Salem.

i can't remember offhand the ages of your kids, but Provincetown may require some explaining. It's loads of fun and we love going there, and I think it helped my kids gain an understanding of gays and lesbians.

Great suggestions, Jeff. I guess I'll be crossing off Gloucester and leave it for the trip that will include Boston and it's surroundings.

My kids will be 16(girl) and 8(boy). Is this place so bad that's a real concern for the kids? My daughter is cool and if there's anything that needs explaining (at this point I'm none will be needed) it's a piece of cake. My little guy is not so easy, though.

When are you planning on going Alex, and for how long?

Hey Rick, long time no hear. I'm still working on my schedule and obviously the itinerary, but preliminary we're looking at beginning of July. The trip will be at least 1.5 week long, but most likely I'll try to make it a two weeks trip.
 
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Coming from NY or NJ...Here is my trip:

Block Island
Cuttyhunk
Vineyard Haven
Nantucket
Edgartown
Menemsh
Newport

My favorite anchoring night spots are: Hadley Harbor/Lake Tashmoo
My favorite anchoring day spots are: Quicks Hole/Tarpaulin Cove

Now you need to tell us what you liked last year and did not like....Where you would like to stay again and longer....Always keep itinerary loose as you might find that spot that you love and want to stay longer......
 
John,

I'm glad you saw this thread. I've learned to keep my itinerary loose and my boating lifestyle is changing (in a good way) ever since I got my 420DB.

Last year we made itinerary adjustments several times: in Block, Edgartown, Nantucket and Newport. These would definitely make the list of destinations I'd love to comeback. We had very nice time in Menemsha, but I think we can skip it and stay some new place. However, I'll always use it as a fuel stop and of course the fresh seafood lunch (whole lobster and lobster bisque). After reviewing photos the crew is drooling about that lunch. I found that Menemsha is not the best spot for spending the night due to being exposed to the channel traffic on a mooring or at anchor. I had to use stern anchor to position the bow on to the channel, otherwise we wouldn't be able to sleep. Gayhead had stunning views, as you advised. I made a number of postcard pix. We ran out of days and due to extra stay at Edgartown and Nantucket, so we never made it to Cuttyhunk. I'd like to spend time on the EIs and do CC this time. I'm looking forward for suggestions.

BTW, my jumping off point will be someplace in LIS.
 
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Then why not hit Cape Cod Canal and Provincetown and try something new? Plymouth? Boston?

All of these are new ports to me.

Cape Cod:
--------------
Provincetown
Plymouth
Chatham
Monomoy Island
Gloucester - not sure if I'm going so much north this time, though.

Elizabeth Islands:
------------------
Cuttyhunk
Hadley Harbor
Woods Hole
Quicks Hole
Tarpauline Cove

I don't think that I'll have enough time to go north of P-town to places like Boston and surrounding are a north of it. I got to leave something for the next time too. :grin:
 
This will give you some old with new....I did this trip and it was a perfect trip for distance (some long/some short) between destination.....I also do not like to spend just one night in most places....i like to relax and enjoy destination.....This is the Cape's version of the great loop....

Previous Destination
Day One (arrive late afternoon): Stop at Hadley Harbor and Spend Night (no services, just a beautiful anchorage)
Day Two Transit: Cape Cod Canal with stop at Red Brook for lunch (chartroom) and fuel and onto PTOWN
Day Two (arrive late afternoon): Arrive in PTOWN and spend night and next day seeing sites/relax and beaches
Day Four Transit (early, early): PTown on outside to Nantucket (whales galore)
Day Four (arrive late afternoon): Arrive Nantucket and spend night and next day seeing sites/relax and beaches
Day Six Transit (mid-morning): To Vineyard
Day Six (arrive early afternoon): Arrive Edgartown/Oak Bluffs/Vineyard Haven 9you pick) and spend night and next day seeing sites/relax and beaches
Day Eight Transit (leave early morning) To Cuttyhunk
Day Eight (arrive early afternoon) Arrive Cuttyhunk and spend night and explore
Day Nine......... Block? Montauk?
 
Thanks John, that's sounds like something that might work. The fuel stop before the canal that's exactly what I was looking for and the cart room looks like a great spot to have lunch and get fuel.
 
Hadley harbor is great - kingman yacht center is a great stop before the canal too Bassetts island is right before it and a great day anchorage too - once your through the canal, shoot strait to p-town (moorings available) (my boys are 9 and 11 and im not worried about it) then you should see whales on the rhumb line from there to salem (again moorings available or stay at brewers) work your way back down staying a night at constitution marine in boston (freedom trail, constitution, north end restauraunts) and then a night on a mooring in the boston harbor islands ( like another world) from there hit Plymouth (again brewers or a mooring) and then back through the canal and revisit any spots you have done before (newport, block, napatree, mystic, montauk, greenport) - as an aside, if you stay at a brewers more than once, ask for a cruising club card (its free) you get half off transient dockage and a $.20/gal discount at your next stop. Pm me for any more info you want - ill get you my e-mail address/cell number - i will be in block for the week of the 4th and may take another week or so and be up that way (green harbor/duxbury)
 
Hadley harbor is great - kingman yacht center is a great stop before the canal too Bassetts island is right before it and a great day anchorage too - once your through the canal, shoot strait to p-town (moorings available) (my boys are 9 and 11 and im not worried about it) then you should see whales on the rhumb line from there to salem (again moorings available or stay at brewers) work your way back down staying a night at constitution marine in boston (freedom trail, constitution, north end restauraunts) and then a night on a mooring in the boston harbor islands ( like another world) from there hit Plymouth (again brewers or a mooring) and then back through the canal and revisit any spots you have done before (newport, block, napatree, mystic, montauk, greenport) - as an aside, if you stay at a brewers more than once, ask for a cruising club card (its free) you get half off transient dockage and a $.20/gal discount at your next stop. Pm me for any more info you want - ill get you my e-mail address/cell number - i will be in block for the week of the 4th and may take another week or so and be up that way (green harbor/duxbury)
What? No 300DA anymore? Darn - first Bridog now this. I am running out of unofficial mentors.
 
Still have it - i had just stepped away from this site for a while - i got in my last 320 da pissing contest an they spanked me good - im done licking my wounds.....alex seems like a great guy so i figured it was a good time to jump back in with some "local knowledge"
 
Very much appreciate it, Mike. It's great to have you back. I'll be digesting all the information and will bug you with more questions. I'm sure I'll have plenty.
 
I guess we can look at the Cape Cod as two different side (South Cape and North Cape). So far I see that on the North side there two ports that are mentioned the most and sounds like must see places Provincetown and Plymouth. Is there anything else I should consider as a must see port on the North Cape side?

Looking at the South side of the Cape, would you guys say that there are ports I shouldn't miss? I'm thinking and looking to get more info about Falmouth, Hyannis, Chatham, Monomoy Island.
 
Not much on the north....Plymouth is not considered the cape. Wellfleet and barnstable are really not geared towards visiting boaters....As far as the south side, Hyanis would be it for me, but most skip it and just do the islands. (I will be doing a trip sometime this summer picking friends up at their place near Hyanis and running to nantucket for a couple of nights) It is cool to anchor in a couple of spots off the west side of monomy but be carefull of the sharks (where theres seals theres sharks!) and honestly, theres not much to see that you wont see elsewhere on your trip (if your doing places like Cutty, hadley harbor, lake tashmoo, lamberts cove, etc) - the same goes for chatham, skinny water, a small harbor, and not much to do unless you know someone with a place there (and it is $$$) - its not that these places are bad, its just that you can do much better and get more "bank for your buck" elsewhere as I had said before, Kingman in Cataumet (mooring or slip) is on the cape and a great stop (along with Bassetts Island) before going through the canal. If you dont want to go as far north as Boston/Salem Plymouth is about 20mi due west from p-town and before heading that way see the whales by venturing out around the backside of p-town as the whales are there during the summer too (follow a commercial watch boat if in doubt)
 

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