Smitten with Lady Liberty

By Donald Cheney
For Points East

It all started 27 years ago when I moved to the North Shore of Massachusett, and bought my first boat. Five boats later, in 2011 – at the age of 65 – I bought the boat of my dreams: a 1995, 38-foot, twin-diesel Grand Banks Eastbay.

Like a lot of boaters, over the next four years I never traveled more than 150 miles north or south from my homeport, nor put on more than 500 miles in an entire summer. Even so, I’d always enjoyed reading the great cruising stories in Points East by such authors as Joel Gleason, W.R. Cheney (no relation), David Roper and David Buckman.

Lacking the expertise and experience of those authors, I never had the confidence to undertake a long cruise to an unfamiliar, distant destination. However, significant changes occurred in my life between 2012 and 2015 that made me realize I’d better fulfill my yearning to cruise someplace new and exciting while I was still “young.”

In the summer of 2016 I finally got up the nerve to take my Eastbay, renamed Smitten, on two dream cruises – one from my hometown of Newburyport, Mass., south to New York Harbor to see the Statue of Liberty, and on to Barnegat Bay; the other, north to Maine to explore Penobscot Bay and visit Southeast Harbor. Combined, I visited 15 destinations in six states and traveled over 1,000 miles in just 25 days. I hope to encourage boaters who’ve never cruised outside their comfort zones to do it now. I am sure glad I did.

I chose all of my destinations with the objective of cruising no more than 70 miles (or about five hours) per day, and to ensure fuel was available every two or three destinations. To help me select my destinations, I used for marina and mooring reviews. I made most of my reservations two to three months before the trip began, and was glad I did. Most of my reservations were made on, a convenient marina app.

I became familiar with the entrance to, and docking arrangement at, each destination using Google Earth maps. I purchased a VHF radio with AIS (Automatic Identification System), which I connected to my chartplotter. This was very helpful wherever there was lots of commercial shipping, such as in the East River and New York Harbor. Lastly, because I lacked skill docking in tight spaces, or in difficult conditions, I took docking lessons from Capt. Rick Kilborn of Boatwise Captains (

Newburyport to Plymouth (about 64 miles)
Newburyport is a great a place for boaters to live and visit, but, before entering or leaving the harbor, they should be aware of the dangerous sea conditions at the bar at the river’s entrance. On an outgoing tide, the Merrimack River’s narrow entrance receives an enormous volume of water, which creates strong currents. This, plus the shallow depths just outside its jetties at low tide, can produce four- to six-foot (and higher) standing waves whenever substantial winds or swells are out of the east. If you are uncertain about conditions at the bar, you can call the Merrimack River Coast Guard Station for an update at 978-465-5921.

I left my home marina, Merri-Mar Yacht Basin, for New York City on June 17, assisted by my enthusiastic but inexperienced crew and bride, Clare Macdonald. I timed our departure to coincide with slack high tide, and, as anticipated, the river’s entrance was as calm as a millpond. The weather and sea conditions could not have been more perfect to begin a 16-day cruise.

To save time, I chose to go around Cape Ann instead of through the four-and-a-half-mile Annisquam River/Blynman Canal. Because of its no-wake requirements, and the narrow Blynman Bridge at its southern entrance (at which boats often must wait for an opening), the Annisquam takes longer, except when seas are rough.

I ran Smitten well inside of Rockport’s offshore breakers, which can be hard to see at high tide or fog, around Straitsmouth Island, and in between Thacher Island (with its two giant lighthouses) and the small pole that marks Landoner Rocks. Once clear of Thacher, I headed straight for Scituate, then followed the coastline down to Plymouth.

The entrance to Plymouth’s harbor consists of a long and winding channel that is best undertaken when there’s plenty of light and water. After finding the Plymouth Yacht Club and tying up to one of its moorings, we had lunch at the nearby Surfside Smokehouse, and walked over to Plymouth’s famous Rock. The next morning, since the day’s leg to Vineyard Haven would only take a few hours, we treated ourselves to breakfast at the Water Street Cafe.

Plymouth to Vineyard Haven (about 39 miles)
Menemsha, not Vineyard Haven, was my first choice for our second destination, but Menemsha was booked up months in advance. However, Vineyard Haven turned out to be one of our favorite stops of the trip. And getting there was half the fun. The Cape Cod Canal is a scenic must, it’s the shortest way to get to Vineyard Haven, and its eastern entrance is one hour from Plymouth.

You can’t rush a canal transit, so relax and enjoy its two huge bridges and bicycle paths along each side. There’s a strictly enforced eight-knot speed limit along the waterway’s seven-mile length. On the day we transited it, we saw seven law-enforcement boats from various agencies cruising up and down the passage. But the 45-minute transit provides a safe and scenic shortcut through the neck of the Cape to Buzzards Bay and the islands.
Once in Buzzards Bay, it was a 40-minute run to Woods Hole. A lot has been written about the cut and its infamously strong currents, its rocks, and its dogleg turn (see “Go with the flow . . . or not” by Greg Jones, Points East, June 2016). Our passage, timed for a half-hour before high tide, turned out to be a breeze. Of course, it helped to have Smitten’s two 300-horse Cats and no traffic where it mattered.

Once into Vineyard Sound, we tied up at the long dock of the Vineyard Haven Marina just 20 minutes later. I don’t believe there’s another marina south of Maine with as pretty a little beach adjacent to it, and a more gorgeous view of classic wooden sailboats to ogle. We had dockside views of Vineyard Haven’s two large resident schooners, the Shenandoah and Alabama, the smaller schooner Juno, and a half-dozen other classic sloops and yawls in front of the Gannon and Benjamin boatyard.

Although it hadn’t been a long trip from Plymouth, it had been tiring, and Clare and I were ready for some good food and drink. So imagine my delight when I realized it was only a 100-foot walk down the beach from our marina to the Black Dog Tavern, with its fun, old nautical ambiance, great food, excellent service, and an unbeatable view of the harbor. And yes, despite Vineyard Haven’s dry status, the Tavern now serves beer and wine. The Black Dog Complex also has a great bakery, where we picked up coffee and pastries the next morning before filling up at a nearby fuel dock and heading off for Block Island.

Vineyard to Block Island (about 60 miles)
Of the possible routes to New York City, I chose to go along Long Island’s north shore because it was shorter. The stop recommended by everyone back at Merri-Mar was Port Jefferson (or “Port Jeff”). Block Island was about halfway to Port Jeff, so we set a course for that little island off the Rhode Island coast. We headed out into our first long stretch (about 30 miles) of open water, with strong south-southeast winds and a three- to four-foot chop.

Five hours later we arrived in Great Salt Pond, (aka New Harbor), where you’d think it would be easy to find the Block Island Boat Basin, one of the Pond’s largest marinas. But it wasn’t. The trick is to keep going up the harbor until you see (and hear) a large restaurant and bar on a hill (the Oar House), which is directly above the Basin’s slips.

As we backed into our slip, the southeast wind that had previously caused the chop now, conveniently, made it easier to get both stern lines tied to the dock, and for Clare to tie up to two bow poles for the first time ever. Once checked in, we got our two golden tokens, each for the rudimentary showers in the Oar House’s basement, and we were off to find some much-needed food and drink.

After about a 15-minute walk down a lovely country road, we found Dead Eye Dick’s, where I enjoyed a great swordfish dinner. Once back at the boat, we moved our deck chairs to our boat’s bow, and marveled at the most colorful sunset of our trip. I was glad to be on the dock relaxing at the end of a long and tiring day.

Block Island to Port Jeff (about 75 miles)
Early the next morning I headed for The Race, and then ran along Long Island’s northern shoreline to Port Jeff. Most of the way, we were protected from the chop caused by south-southeast winds, and I arrived at Port Jeff’s entrance just four and a half hours later. The entrance to Port Jeff is wide and easy to recognize, but keep an eye out for the frequent ferries running between it and Bridgeport, Conn.

My mooring reservation at the Port Jefferson Yacht Club proved an excellent choice. Located on the opposite side of the harbor from the ferry landing, it was a short walk past a lovely town green to the adjacent Danford Hotel and its shaded deck overlooking the harbor. Sitting on the deck and enjoying a couple of gin and tonics, while being serenaded by a superb acoustic guitarist, was just what the doctor ordered. Since we had a short way to go the next day, we treated ourselves the next morning to breakfast at a small, locally celebrated restaurant named Toast.

Port Jeff to Oyster Bay (about 17 miles)
We stopped in Oyster Bay because if we’d gone straight to New York City (54 miles away) we wouldn’t have been able to transit Hell Gate under the placid tidal conditions recommended by the guidebooks. But Oyster Bay was a fun stop. It’s easy to pick up a mooring at the Oyster Bay Marine Center, and, upon entering Oyster Bay’s nearby downtown, we were greeted by a gathering of classic cars lining its main street. After talking car stuff with friendly classic-car enthusiasts, we went to the town’s most celebrated restaurant, Canterbury’s Oyster Bar & Grill, where we enjoyed delicious sea scallop dinners.

Oyster Bay to NYC (about 37 miles)
Finally, early on the sixth day of our trip, Clare and I were on our way to New York City. I was excited and relieved that our goal was finally at hand. But I was also apprehensive due to my lack of experience with the volume of commercial boat traffic I knew lay ahead. However, I had prepared myself as best I could by reviewing every stretch of the day’s run on Google Earth and timing it so that we would be at Hell Gate shortly after slack tide on an incoming tide – just as the guidebooks recommended.

Ninety minutes after leaving Oyster Bay, we passed by City Island and were at the Throgs Neck Bridge. Here, we entered the 17-mile-long East River and caught our first glimpse of the New York City skyline. I quickly learned from observing other cruisers heading downstream and barges being pushed upstream, that everyone speeds along at seven to eight knots. This felt faster than I would have liked, considering all there was to look at along the way.

Before I knew it, we had passed underneath the Bronx-Whitestone Bridge, gone around Riker’s Island, in between North and South Brother islands, and were suddenly facing Hell Gate. I had apparently timed it just right because we encountered virtually no current or eddies. Less than 10 minutes later, we passed Roosevelt Island, leaving it to starboard, and caught close-up views of both the United Nations and the Empire State Building. By the time we looked ahead again, we could see what must be one of the most famous and fabled bridges in the world, the Brooklyn Bridge. Then we found ourselves suddenly in New York City’s large and busy harbor, with the Statue of Liberty directly in front of us.

There was so much to see that my immediate reaction was pure awe. Keeping an eye out for the armada of large, orange ferries and smaller, black-and-white or yellow water taxis, I made my way across the large and choppy harbor to get a closer look at Lady Liberty. I had been told back at Merri-Mar that every boater should see her at least once from her or his own boat. The statue’s size (305 feet from base to torch), beauty and majesty can only be truly appreciated when seen up close, and from the water.

Following one of the little yellow ferries, we entered the Morris Canal Basin – on the New Jersey shoreline opposite Battery Park – and backed into a slip at the Liberty Landing Marina. The view of Lower Manhattan from above the marina was stunning. We had completed 294 miles in six days since leaving Newburyport.

Although the day’s trip from Oyster Bay had only taken three hours, we were ready to relax over good food and drink, which seems to be a recurring theme for us. And the Liberty House Restaurant was a short walk away and was open for lunch. Clare and I sat down, closed our eyes, and soaked up the relaxing, pleasant atmosphere as though it was life-restoring water. We were exhausted, but we also were filled with the satisfaction recreational mariners get having arrived safely in a distant port after a long, successful voyage.

Don Cheney and his venerable Eastbay 38 live in Newburyport, Mass. Don recently retired from Northeastern University, where he was a professor of marine biology. He and his wife Clare spend winters at her home in Santa Barbara, Calif. Part II will appear in the September issue of Points East.