Sailing Around Cape Ann

Posted on Saturday 19 August 2006

Since this is a sailing blog, at least to some degree… I should probably write about sailing at some point. As part of my plan for long-distance passage making, I was taking a Macro Cruising Course over at the Boston Sailing Center. I’ve also posted some photos, per Tillerman’s request. I hope you enjoy the story and the photos. By the way, the details of the trip are based on my very faulty memory, and any mistakes in the order of things is likely to be my fault.

My two main reasons for taking this course were: first, to use it as a refresher since I had been out of sailing seriously for about ten years; and second, to get certified to charter boats, like those offered by Moorings or Sunsail. Earlier this week, in the Cruising Course, the final part of my macro program—I went on a three-day voyage that ended up circumnavigating Cape Ann. The course was taught by Norman Martin, who was the skipper of the C&C 38 we sailed on the trip.

Cape Ann, for those who don’t recognize the name, is the smaller of the two capes on the Massachusetts seacoast. Cape Cod, the larger and more commercialized cape, is the one that looks like a bent arm sticking out into the Atlantic. Cape Ann, is the much smaller, but just as important cape that has the historically significant port of Gloucester, and one of my favorite towns, Rockport. It is also home to one of my favorite beaches, Halibut Point State Park, which I wrote about earlier.

Preparations—Getting to Know Melissa

Tuesday morning, we went over the navigation techniques we were going to be using on the trip, as well as what equipment and clothing to bring. We then did a review of the on-board systems on the C&C 38, which differ quite a bit from what I am used to on the Pretty Gee. Our final task for the day was to get some time understanding how a C&C 38 handles under power.

The Boat’s Systems

The major differences between the two boat’s systems can be broken down into engine, water, steering and galley. The electronics, radio, and other systems are fairly similar between the two boats.

Melissa has a 30 HP diesel engine, which is cooled via a raw water heat exchange system, while the Pretty Gee is powered by a 20 HP four-stroke outboard gasoline engine. One task I had was checking and clearing the raw water strainer, down in the bilge. I was elected to do this, since I was the only one on-board with a multi-tool. Norm also showed us how to “hot-wire” the diesel, in case the ignition switch, in the cockpit had any problems.

The water system on Melissa has two tanks and has a pressure water system, with a calorifier, to provide hot water via a heat exchanger from the engine cooling system. The system on the Pretty Gee has only one tank and is not pressurized, so doesn’t require any electricity to use.

The steering system on the Melissa is a wheel-based steering system, which is common on larger boats. I prefer the tiller that is on Pretty Gee, as it provides a good deal more feedback on the way the boat is handling and is balanced. During the trip, I did have a few “tiller” moments, where my instincts to turn opposite of the way I want to, from using a tiller, ended up in strange course corrections.

The galley on the Melissa is much larger than that of the Pretty Gee, and includes a three-burner stove with an oven. The oven is a nice addition and I am looking to see if retrofitting a stove with an oven would be possible on my boat. Norm baked corn muffins one morning, and there is something really wonderful about having fresh-baked muffins while underway. The Melissa also has a stern-mounted barbeque grill, which is something I am planning on adding to the Pretty Gee.

Melissa under Power

Norm had all of us take the helm to understand how Melissa handles under power. The difference between her ability to turn towards port and starboard, the way propwalk affected her ability to go in reverse, and how she pivots around her fin keel were some of the things he wanted us to observe.

The first drill was getting used to how Melissa handled under power. We learned this by motoring her through a mooring field full of Solings and Sonars. Surprisingly, Melissa is fairly responsive under power, and was able to come through fairly tight areas with ease. Much of this is due to her heritage as an IOR rule design racing boat.

The second drill was to turn Melissa around in the narrow area beside the dock and bring her alongside the dock. We did this both to port and starboard…as the turning capabilities differ a bit between the two directions under power. The boat tends to turn more tightly to port than to starboard. This is mainly due to prop walk, caused by the rotation of the prop. Shifting into neutral tends to cancel out the effects of prop walk.

The last drill under power was one that can be challenging, and is very important. It was to try and back Melissa into a marina slip. This is a very difficult thing to master, and the way it works for each boat is a bit different. The wind and current also affect how this works out.

Two things that most people had to learn, because a boat handles a bit differently from a car, are: Boats have no real brakes, this is especially true of heavy, underpowered sailboats while motoring; and that boats pivot around a central pivot and do not follow the front of the vehicle as happens in a car—this is important as the back end of the boat swings out as much as the bow swings in, rather than just the front of the boat swinging over.

Starting Off

On Wednesday, I showed up at the Boston Sailing around ten-thirty. A few minutes later, Mike and Tom, two of my fellow crew mates, showed up. Tom and I helped prep the Melissa for the upcoming trip. This mainly involved getting the water tanks topped off, and putting the jib on the roller furling gear, while Norm and Mike went off to get more provisions. A few minutes later, our other two crew mates, Dren and Cheryl, showed up.

Next task, since the crew was all here, was to take the boat over to the fuel dock, in Chelsea. We motored over to the fuel dock, and had them top the diesel tank off, about four gallons, and pump out the holding tank for the head—the boat’s version of a sewage system and bathroom.

The sails and clouds—a deck level view.Since this was the first time for the six of us as a captain and crew, as well as the first time most of us had been on a C&C 38, Norm had us take Melissa out and handle her under sail as a team. He wanted each of the five of us to take a turn at the helm, and for us to work the different positions on the boat—bowman, the pit, trimmer, etc. On the right is a photo I took on the last day, Friday, while lying on the port sidedeck, and looking up at the clouds and sails.

The goal was to get the crew familiar with the sail and rigging layout on a C&C 38. Every boat has a slightly different setup from another, and the rhythm of the movements, between the helm and the sheets is also slightly different from boat to boat, even within the same kind. We did tacking and gybing drills with the boat, through the mooring field, to get a feel for how she handles under sail, and to get a better idea of what the rhythms of her rigging during a tack and gybe are like. A C&C 38 handles quite nicely under both power and sail.

Norm, Tom, Dren and Cheryl, as we leave Boston HarborNorm then had us bring Melissa back to the dock and tie her up. It was time to get going. We tied the dinghy to a cleat off the stern and headed out of the slip and out of Boston Harbor. On the left is a photo of Skipper Norm on left, Tom at the helm, and Dren on the genoa sheets, as we are leaving Boston Harbor. Cheryl can be seen in the lower right of the photo, and the building in the center of the photo is one of the ventilation buildings for the Big Dig tunnels.

Leaving Boston Harbor

Cruising Boats Racing on Boston HarborOn our way out of Boston Harbor, we watched the informal evening race between the larger cruising boats associated with the sailing center. Some of the boats racing are owned by the sailing center, and sailed by members, others are owned and sailed by former students or members, past and present, of the sailing center. This photo on the right shows some of the boats we saw racing.

It was just past sunset, as we made it out of Inner Boston Harbor and started to make our way through the Outer Harbor and out across Massachusetts Bay towards Manchester-by-the-sea. We cut across the Presidents Roads shipping channel, using a range between the Deer Island Light and the “PR” buoy to keep us safely south of Aldridge Ledge. We then headed out through Hypocrite Channel, using the range formed by the Long Island light and the “15” buoy to keep clear of Roaring Bull and the Graves. Mike did a great job at the helm, and was able to keep the range directly astern of the boat. Once out past the Graves, we turned north to head to toward Salem Sound, where the plan was to anchor out behind Great Misery Island.

Dawn on the hook, behind Great Misery Island.We headed north and Norm had us enter Salem Sound via the Children’s Island Channel. Great Misery Island separates Salem Sound from Manchester Bay. We dropped anchor in about 17’ of water, on the north side of the island. The photo to the left was taken just before sunrise, on the hook at Great Misery Island.

Headed to Rockport

The next morning, we headed out, bound for Rockport, which was going to be our final destination for the night. As one of the navigation challenges, we went through Magnolia Harbor, which is sheltered by Kettle Island, and is unmarked with several shoals to make our way around.

After leaving Magnolia Harbor, we headed up to Gloucester Harbor. Norm wanted us to see a few things in Smith Cove, which is on the eastern side of Gloucester Harbor. One of the important things that Norm wanted us to see was a RG buoy, which shows the fork for the primary and secondary shipping channels in Gloucester harbor.

We then went south and east from Gloucester Harbor, and up around Eastern Point. Our next goal was to anchor in Brace’s Cove. Brace’s Cove was where we were going to drop anchor for lunch. Like Magnolia Harbor, Brace’s Cove is unmarked. Entering Brace’s Cove, Tom made an interesting discovery. There is an unmarked rock that extends to about 3’ from the surface. The water next to the Tom’s Rock is over 16’ deep, and the rock is about the size of a house. Norm marked the rock on the GPS and his chart of the area. Fortunately, Tom found this rock by spotting it as he made his way into the cove, rather than by hitting it with the boat.

Dren at the helm, while Mike, Norm and Tom look on.Our next goal was rounding Cape Ann. Cape Ann is one of the most treacherous capes on the Eastern Seaboard. Historically, it was an important landmark for ships approaching the ports of Boston, Portsmouth, Newport, and New York. We went outside Milk and Thacher Islands, which lie to the east of Cape Ann. Thacher Island is unusual in that it has two lighthouses on it. The twin lighthouses were a clear indicator to ships approaching Cape Ann of their position. Today, only one of the two lighthouses, the easternmost, is in use. In this photo, Dren is at the helm, while Mike (left), Norm, and Tom look on. Mike is probably handling the genoa and mainsheets.

The next part of our journey brought us outside Straitsmouth Island, and inside Little and Dry Salvages, two shoal areas which were a serious threat to navigation in the past. One major danger, as we approached Sandy Bay, was the mostly submerged breakwater, that was installed to help shelter Rockport Harbor and Sandy Bay from winter Nor’easters.

In Rockport Harbor, Rockport, Massachusetts

Rockport Harbor Entrance at DawnTom radioed the Rockport Harbormaster and asked for our slip assignment. We were assigned the slip I had hoped, the one along side Motif #1. This was our goal for the night. This is a photo of the Rockport Harbor entrance at dawn, on Friday morning.

Mike and Dreams on an ApronDinner in Rockport was steaks and chicken on the barbeque. Dren brought the steaks, from the Hilltop restaurant, and was responsible for grilling some of the best steaks I’ve had in a long time. To the right is a photo of Mike in Norm’s apron, which shows the area Mike wants to cruise in.

Melissa, a C&C 38, and Motif #1Motif #1 is the subject of many paintings, drawings and photographs. It may be the most photographed and painted building in the United States. The current building, which I refer to as Motif #1 v.2, is a replica of the original, which was built after the original building was destroyed in the Blizzard of 1978. On the left is a photograph of Melissa and Motif #1, as seen shortly after sunrise on Friday morning.

Leaving Rockport Harbor

Rockport Harbor Entrance at SunriseFriday morning was a fairly early one—we were planning on going down the Annisquam River, but in a boat that draws seven feet, making it within three hours of high tide is important. The sunrise over the Rockport Harbor entrance is shown in the photo on the right.

Norm left for the Sandy Bay Yatch Club and asked the five of us to meet him over there with the boat, and pick him up. We cast off the docklines, and motored through the very tight confines of Rockport Harbor to the floating dock at the SBYC, where we rinsed off the boat, and topped off the water tanks. Then it was time to go—we had a river see.

To the Annisquam

Cheryl at the helm, with Mike and NormNorm’s plan for the day was to separate the crew into two-person teams, and have them handle the boat double-handed, as they would if they were chartering the boat as a couple. Chartering boats as a couple, and cruising as a couple were the eventual goals of Mike, Tom, and Cheryl. Dren and I both wanted to sail, but neither of us has a spouse to bring along at the moment. Here is a photo of Cheryl, flanked by Mike and Norm, at the helm, on our way to the Annisquam.

The Watchtower at Halibut PointAlong the way to Annisquam river entrance at Annisquam Harbor, we rounded Halibut Point. Halibut Point is one of my favorite beaches. I took the photo of the Halibut Point’s beach, and you can see the park headquarters, which are housed in a World War II-era submarine defense watch tower. Notice the steeple attached to the tower, which was supposed to make the Germans think this was a church.

On the Annisquam River

A house along the Annisquam RiverThe Annisquam River cuts across Cape Ann, connecting Annisquam Harbor with Gloucester Harbor via the Blynman Canal. There is a draw bridge across the river, along the way. Some of the houses along the Annisquam are magnificent, and many different types of architecture are represented. Here is one such house—Dren, an architect, told me what style this house was, but I’ve since forgotten.

An oddity, particular to this part of Cape Ann, are houseboats—not the traditional houseboats that you might see on a lake—but little houses built on rafts. Here’s a photo of three such legacy houseboats, on the Annisquam River. The Essex River also has a few of them as well. New ones are not permitted, but these three are grandfathered. Houses on Rafts, Annisquam River

We hailed the bridge and it soon opened. We were following another sailboat through, and out into Gloucester Harbor. The canal exit is on the Western Harbor basin, near the famous Fisherman statue. Once we were clear of the harbor, we put the sails back up and headed down to Boston.

Gloucester to Marblehead

One team, I think Tom and Dren, was responsible for bringing the boat down from Gloucester to Marblehead. The really interesting part of the section of the trip was hearing about a boat that was requesting a tow just off of Childrens Island and the Marblehead Channel. Apparently, another sailboat was a bit careless in their navigation and had gone aground. While they weren’t taking on water, they were stuck pretty solidly. I believe they were aground on the shoals just west of Childrens Island, where the chart has several places marked two feet or less of water at mean low water.

Marblehead to Nahant

Mike and his lap autopilot, on the way to NahantNorm asked me to bring us down to Nahant, but to take a course west of the Outer Breakers. Mike was the helmsman, and I was navigating. Starting at the RG buoy in Marblehead channel, I plotted a course south past Tinkers Island, and then to the southwest, into one of the channels through the Breakers. Once through the breakers, I had Mike steer South-by-Southwest towards the red “2” buoy off of Nahant. Here is a photo of Mike, demonstrating his lap autopilot technique.

Cheryl navigating, pop-up prairie dog styleNahant to Boston Harbor

Once off Nahant, I handed it over to Cheryl and Dren, who brought us back into Boston Harbor. I think they took a route south past the Graves and then into the Outer harbor via the Hypocrite Channel, we had left by two days earlier, but I was being a passenger and not really paying attention. Here are two photos. The first is of Cheryl, using the Mark I eyeball to figure our position. The second is of Dren, at the helm, checking the jib tell-tales.

Dren at the helm, checking the jib telltalesBack in Boston Harbor

Dren setting out beer after getting back to the dock.Dren brought us into the dock at the BSC. Once we tied up, we had a few things to do, like neaten the lines, cover the sail and put away the dinghy. Here is a photo of Dren, working hard at one of his last tasks for the voyage, putting out beer for the crew.

2 Comments for 'Sailing Around Cape Ann'

    August 21, 2006 | 4:24 pm

    This is one of the best posts ever on this blog. Great sailing story and excellent photos to supplement it. Keep up the good work.

    August 21, 2006 | 4:33 pm


    Thanks, I hope you don’t close down your blog, as I’m shooting for making your list again. 😀

    If you want a print of any of the photos, let me know, I’d be happy to send you one.


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