Gloucester is a fine place... welcoming yacht club... stopped over and had a dinner there.

If I am sailing that far (from LIS) I prefer to cruise Penobscot Bay.

 

My New England sailing and delivery days were very long ago, so "don't quote me" but, in general,

You going outside the Cape, or through the Canal? I think Canal would work better, a more sheltered and forgiving geography. But of course you have to time it for favorable current. Annisquam you have to wait for the bridge anyway. So Rockport might be nice if you go outside Cape Ann. Either Plymouth or P-Town is along your general path but P-town itself is "right there", while Plymouth is shallower and a long way in and back out. Buzzards Bay is full of great little harbors, and anything west of Buzzards or Narragansett Bay, I know diddly squat.

Best wishes! Sailing in New Orleans is "different", big lake and not that many harbors.

 

Plymouth is a bit of a long windy motor to get in, watch your draft inside. P-town is deeper easy in, but more exposed to weather and could be a long dinghy ride from one of the outer moorings. Scituate could be a consideration for you.

I too looked at Annisquam as an alternate route, but my mast ht. and draft are much less than yours. I think I'd be a little nervous with 7' Hope you get a report from someone who's done it recently.

 

If you're at the Dolphin Marina in Harpswell, be sure to get some blueberry muffins. They are the best. Kennebunkport is tight, crowded, packed with tourists and not deep or cheap. Cape Porpoise might be better, though there isn't much there. Wells does not have much to offer. Biddeford Pool is nice, but doesn't give you much of a run that first day. Portsmouth NH and Kittery are likely more interesting, though the current can be formidable. THE restaurant in Portsmouth is Jumpin'Jay's Fish Café. We hear good things about the Isles of Shoals. You are consulting Taft's Cruising Guide to the Coast of Maine, of course.
Would second SanderO's suggestion of Gloucester. The Eastern YC is right at the harbor entrance and welcomes visitors warmly. Last I heard they offered free ice to boats that moored overnight. Marblehead is also not far off the track. P-town can be zooey. We put in there on a weekend and had to slalom through the runabouts to get tied up at the fuel dock. A whale surfaced next to us on our way in though, making it pretty special. The harbors in Massachusetts Bay south of Boston tend to be shallow and shifty-sandy. Plymouth, as mentioned, is a long way in and out. Narragansett Bay is full of great spots to stop. We took a mooring at the Pope's Island Marina in New Bedford last year and had a great time. Besides the whaling museum there are seafood restaurants all along the harbor front and a marine hardware store across the street from the marina.

 

My 2 cents. Eastern Point Yacht Club in Gloucester is an option, but it is a long dingy ride to town and I don’t know if the public launch comes out that far. I usually get a public mooring which are in the inner harbor. You will be in with some of the commercial fishing boats but a quick ride to town. Also I once anchored overnight when there were no moorings available. It was in the area between the mouth of the Annisquam and Stage Fort Park. I don’t think it is on the chart but harbor master directed me there. And don‘t think the Annisquam is worth while short cut. But if you go, Mile Marker 1 is a fun restaurant and good brunch.
P-Town is a fun place with great restaurants. It use to be a good place to dock or catch a mooring, but over the last several years a corporate entity bought up most of the water front and really jacked up their price. The anchorage there is good but as mentioned above a long dingy ride to town. And when you get to town there is no place to keep your dinghy for any period of time. Plymouth is a decent stop with some nice restaurants. But it is a long way in and can get skinny in areas. The bonus for Plymouth is that it is really close,to,the mouth of the canal.
Of course between Gloucester and the canal is Salem Harbor. The new Hawthorne Marina has reasonably price moorings with launch service and a short walk to town. Boston Harbor is an option. If you want to go down town contact Boston Harbor Sailing Club and see if they have a mooring available. If so you will be right off of Rowes Warf. If you are looking for quiet or don’t want to go deep into the harbor the Islands at the entrance of Boston Harbor are gems. There are several moorings off George’s Island and the East side of Long Island. And more that I can’t think of at the moment. You can call to reserve them. Also as mentioned above Scituate is a nice stop, but it gets a bit skinny in there too.
As far as choosing, since you have options maybe go where the wind takes you.

 

I've done the trip a few times;

Kennebunkport - hard to pick your way in through the amazingly dense deployment of lobster pots. Stayed on a mooring, and was waked at 3:am by every lobster boat heading out to sea buzzing us at full throttle. Great wine and cheese shop, and seafood restaurant. I would not go again

Portsmouth - I stopped at Isle of Shoals and picked up a mooring. Do NOT try to anchor here. Very nice to walk around Star Island, and use their shower. Watch out for poison ivy!

Annisquam River - never been through it. Not worth the detour. It is meant for powerboats.

Consider stopping in Scituate. Easy to get into, easy to get out of, and very well protected. Easy to re-provision at the Stop&Shop across the street. Good restaurant.

Plymouth - 1 hour to get from the channel entrance to the town. Really great town, once you make the trip in. Lots of restaurants, and you will stay on a slip at the Safe Harbor Marina, because it is the only choice.
P-Town - Easy in, easy out. You will stay on a mooring, and there is a launch service that will bring you to the town dock. Very well protected, and you will probably see whales on your trip across the mouth of Cape Cod Bay.

I would stay in P-town if you are on a schedule, and Plymouth if you have time to explore.

 

You'll have a dinghy? If so, many more harbors you could try, since no marina needed, just a public dock. PaulK above mentioned Marblehead. I grew up and learned to sail there, lucky me. Much history there within easy walking distance from the State Street Landing public dock. More compact than Salem. Not that far from Gloucester.

I sound like the Chamber of Commerce ;-)

 

Hello Everyone,

Thanks for the information and advice.

Some updated / additional information
-i won't have a dinghy
-I prefer to alternate between mooring and slip, so one night on a mooring ,the next in a slip
-I'd like the trip home to be a cruise and not a delivery. However, it I lose too many days due to bad weather it will become a delivery.
-I might start the trip home a day or two sooner so I have more options

Any info on the Biddeford Pool area?

Thanks,
Barry

 

You need a copy of Taft's Guide to the Maine Coast if you don't already have one. It has info on just about any place you might want to tie up or toss an anchor.

 

I don't recall too many moorings... but anchoring in that tide range is very challenging.

 

I haven't been around there in years. But back then, it was "no". If you're a Yacht club member you might get reciprocal privileges. You could probably tie up at the State Street Landing public dock, but not for long, it's meant to be transient, for small dinghies mostly, and also where the commercial fishers tie up to unload.

Pardon me for being obtuse, but without a dinghy, how are you going to explore those nice harbors on shore?

 

Hi,

My plan is to stay in a slip at a marina, or on a mooring with launch service.

Current plan:
Depart Mt. Sinai Friday afternoon and sail directly to Portland (through the Cape Cod Canal).
Stay at Dimillos in Portland Sunday- Tuesday. Wednesday sail to Harpswell and stay on a mooring at the Dolphin Inn ( get some coffee and muffins). Thursday start for home by sailing south to Biddeford Pool (on a mooring at the yacht club). Friday go to Portsmouth (slip at Kittery point). Saturday go to Salem. Sunday go to the cape cod canal, spend the night at the Sandwich Marina. Monday go through the canal. The rest of the trip is up in the air.

If we encounter bad weather we will stay in port and try the next day.

Barry

 

If the current is ebbing when you get there; rather than stay in Sandwich at the east end of the canal, I would go to Onset at the west end of the canal.

 

If you go through the canal and are anywhere in Nantucket Sound, all the yacht clubs welcome members of other yacht clubs. Particularly, Hyannis Yacht Club has launches, showers, a restaurant, etc.

 

With a 7’ draft I would definitely not attempt the Annisquam…

 

Hello,

On Friday Aug 12 I depart Mt. Sinai NY bound for Portland Maine. There will be 5 experienced sailors aboard and we plan on sailing non stop to Portland. I will be spending 5-6 days in the Portland area, staying at Dimillos, The Dolphin Inn, Safe Harbor Great Island ,etc while there.

The following weekend, either Saturday or Sunday Aug 20-21 I plan on departing for home. I'm not sure if this will be a cruise home or a delivery or a bit of both. I've been studying the charts, cruising guides, etc , but I always prefer local knowledge. So, I would appreciate it if you could share some wisdom and experiences.

1. Kennebunkport - My boat draws 7'. Can I get into Kennebunkport? Some reports list 6' others 8' Is Chicks Marina really $6.50 / ft? That seems crazy. What else is available? Dimillos Kennebunk? It seems like Portland to Kennebunk is 4 hours, which would be good for a first day trip

2. Portsmouth - Looks like there is plenty of water and lots of places. Any recommendations? It seems like it would be 7-8 from Portland to Portsmouth, or 4 hours from Kennebunk

3. Annisquam River: Can this be traversed by a sailboat with 7' draft and 65' air draft? If the weather is snotty this looks like it would be calm.

4. Plymouth vs Provincetown. Which would you recommend as a stopover? It seems to be about the same distance from Gloucester to either one. Which place has better moorings, dockage, restaurants, getting into / out of ?
For amenities they are
5. After that it's back through the cape cod canal and more familiar waters for me.

thanks,
Barry

If you’re going thru the CC Canal, I’d recommend Plymouth…. For amenities, P’town is more vibrant, but Plymouth has plenty of options…

 

Greetings from Maine!

We made it! As planned, we departed Mt. Sinai at 3:00pm Friday and arrived in Portland around 10:00am Sunday.

The trip was mostly smooth. The first night had light air and a lot of motoring. We did get 4 hours of peaceful sailing late Friday night into Saturday morning. The trip up Buzzards Bay had wind against tide and was uncomfortable but manageable. The cape canal transit was fun and fast, 10 kts w a favorable tide.

Then we exited the canal and it went downhill, fast. Wind 15-20 from the north, current from the south. Ouch. We were pounding into steep chop, launching off of waves. No good. We turned down 30 degrees and motored w the main up. After 30 minutes I was done. We studied the charts for a bailout. Provincetown to the northeast or Plymouth to the north and west. PTown it was. We cracked off and motorsailed there at 6 kts. The plan was to get out of the wind and seas, anchor, rest, eat lunch, and come up w a plan. At 30 degrees apparent wind the ride was bad but not terrible, so we sucked it up and kept on. 2 hours later we were in the Lee and things improved. We saw whales, dolphins and other marine life. A few minke whales surfaced right behind us, close enough to smell the whale breath (not pleasant).

We motored into the harbor and dropped anchor. Ahh, no more pounding. A boat that didn’t bounce around. I made lunch for the crew and we relaxed in the warm sun. 45 minutes later, after studying the weather, and reviewing our Options, we had a plan. The wind was forecast to move west and get light. Good. If the seas stayed up and the wind stayed up , we would divert to Portsmouth. If the weather was as forecast we would continue to Portland.

We departed PTown and beat NW. The whitecaps we’re depressing. We actively steered around the waves and the ride was bad but bearable. Slowly the wind did clock and decrease. By 8:00pm we ate Costco lasagna in the cockpit and watched a beautiful sunset. ETA to Portsmouth was 3:00am, not good, ETA to Portland was 9:00am. okay, to Portland.

The rest of the trip was fantastic. I slept for 4 hours and joined the crew at 0100. The wind moved west. We unrolled the headsail, turned the engine off at 130 and sailed at 6 kts due north. We never started the engine again until we reached Portland. The sun came up, bright and warm, the wind got light but we kept moving along nicely. What a wonderful change from the day before. I understand why so many boats are named perseverance!

Eventually we reached Portland harbor, hailed Dimillos, got a slip assignment, tied up, and shut down. The we had a dark and stormies and toasted our good fortune!

A few hours later my family arrived and the delivery crew departed. Now it’s vacation time!

Barry

 

Pictures

Good times

 

Good onya and well done!!

It kind of reminds me of deliveries I used to do on occasion out of Marblehead where my Dad sold new and brokerage sailboats. This was long long ago. You just keep going, and duck in when you have to. They actually trusted me to do this starting when I was 17, on short hops in Mass or up to Rye New Hampshire, then longer trips when I was all of 19 or 20. As far "down East" as Southwest Harbor, and to the west as far as Newport and Block Island. I generally put in overnight though. Good memories for me, looking back.

Now you get to take it slow and enjoy it! Though it sounds like you enjoyed the "delivery", too. There's a satisfaction in having a "passage", and making it in good shape despite some rough patches.

Best Wishes, and thanks also for helping me recall those good memories.

 

Hi,

We sailed from Portland to Kennebunkport today. The wind was west, and pretty strong. Since we were heading south we had a fast run down the coast from Portland to Biddeford. When we had to turn a little more west we started seeing 20+ apparent wind speed. A reef in the main helped flatten the boat. Eventually we made past Cape Porpoise and then the wind was on the nose. So dropped all sail, motored and then went up the river to Chicks.

The place is not as crazy crowded as I feared. Perhaps because it's a Thursday there are less people here. We depart tomorrow morning for Portsmouth / kittery Point.

Barry

 

Many lobster pots?

 

Is the Pope Catholic?

 

Continuing the vacation saga:

We walked to town in Kennebunkport and had a nice breakfast at Mike's All Day Breakfast. The supply truck broke down, so no supplied for Mike and no blueberry pancakes for the Lenoble clan. We made do and no one starved.

The forecast was for light wind from the west, moving south. I expected to be motoring the entire time. We departed at 1000, with low tide at 1130. So we stuck to the center of the channel and saw 6.8' on the depth finder a few times. My boat draws 7' so it was close. We were about 100' from the end of the channel when we did touch bottom, but only for a bit. I finally relaxed when I saw 15'.

Out in the ocean we raised the main, and shook out the reef from yesterday. I was surprised to have 10 kts of wind, on the beam, so we quickly unrolled the headsail and shut down the engine. We were moving at over 6 kts and i figured we would sail until we ran out of wind. That never happened. Instead the wind was up and down all day. It would build to 15 true and move west, then lighten to 9-10 and move south. After heeling 30 degrees I got tired of that and we reefed the main (again) and even rolled up some of the headsail. Still we had a fast fun sail. When we reached Portsmouth we dropped all sail and started to motor in.

So I had thought I'd seen lobster pots before having dodged them up and down the coast once we reached Portland. I was wrong. The entrance to Portsmouth has the most lobster pots I have ever seen. And they seem to be everywhere. In the channel, out of the channel, just everywhere.

Anyway we're docked at Safe Harbor Kittery point. It was a quick 330 hour trip here. Lunch is done and cleaned up after. I'm reviewing plans for the tomorrow (Salem) and beyond, checking weather, looking for restaurants, basic sailing vacation things.

Last item - we haven't seen whales since Provincetown. We have seen 3 mola mola's, which are the strangest creatures ever. They just sort of float along the surface and seem to smile and wave as you pass them.

Pictures to come once I get better internet.

Barry

 

Hello,

Vacation is over. The boat has been emptied, washed, and is back on her mooring.

Since my last post, my family and I sailed to Salem, ma. An old friend arrive, my family departed, and we continued the cruise. From Salem we went to Plymouth, then though the canal to the New Bedford yacht club in pandamar, then Bristol (and the Herreschoff museum and Americas cup exhibit), the. Block Island, Westport, and home.

Everyone aboard had a good time. The boat was fantastic - no problems at all (well I did need to tighten the alternator belt and the stove igniter stopped working). I traveled over 600nm in two weeks and used about 60 gallons of diesel.

Barry

 

Hello Barry, I used to sail out of Mt. Sinai on a Catalina 30 (Polaris) I'm now a 100 ton USCG Captain living in Saco Maine. Sounds like a good trip you have planned. What I can tell you about Kennebunk Port is that the tides can be 10' difference between high and low tide about every 6 hours. so if you are going up the river plan accordingly! You can also make it up the Saco River (again watch the tides and follow the charts. If you would like a guide up the Saco River I'm more than happy to meet you at the mouth of the Saco River. There are some tricky currents at the dock during the tide flip (camp Ellis Pier) I could jump aboard for local knowledge up the river if you would like. (nice anchor/mooring spot in "cocktail cove" on the Saco RIver). you can reach me at Captaincanto@gmail.com to talk more in depth about your trip. All the Best, Jonathan

 

Obviously you did this trip in 2022! I did not see the date until I sent my message. If you decided to come up to Maine again drop a line!