Cruising America’s Great Loop Part Six

John Simons


Our Great Loop adventure took one year and covered 6,500 miles. We departed from Waukegan Harbor in mid-September 2015 and, after making a series of left turns, returned to Waukegan Harbor in September 2016. Our crew consisted of John and Priscilla Simons and Dale and Andy Arnold.

Hundreds of “Loopers” make this trip each year. America’s Great Loop Cruising Association conducts seminars to help Loopers prepare for the adventure.

If you’re just tuning in, catch up on our journey:

  • Part one — Waukegan, Illinois, to Grand Rivers, Kentucky
  • Part two — Grand Rivers to Mobile, Alabama
  • Part three — Mobile to Key West, Florida
  • Part four — Key West to the Bahamas and Stuart, Florida
  • Part five — Stuart to Norfolk, Virginia.

To paraphrase Mark Twain, the coldest winter I ever spent was a May in Norfolk, Virginia, for the 2016 Looper Spring Rendezvous. But, unseasonable weather notwithstanding, if you cruise America’s Great Loop, you’ll want to attend both the fall and spring Looper rendezvous. Not only will you meet fellow Loopers you’ll see again down the road, but you’ll also collect invaluable information on where to go and what to do on your next leg.

Norfolk ≫ Portsmouth, Virginia

After constant rain throughout the night into the early afternoon, we pumped out before casting off for the half-mile Elizabeth River crossing to Tidewater Marina in Portsmouth. We left Changing Latitudes there for the better part of a month.

During that time, Priscilla and I flew to Boston to visit grandson Jackson, to Chicago to see granddaughter Eleanor, and then to Stuart, Florida, to close on our condo. Dale and Andy spent several weeks in Chicago.

After returning to Portsmouth, we stayed a few days to put together our cruise itinerary for the section between Norfolk and Waukegan. Even though the collective wisdom of cruisers advises against having firm dates for travel, if you cruise at 30 mph, you can make just about any itinerary work—weather permitting.

After nearly a month’s stay in Norfolk and Portsmouth, we couldn’t wait to explore the Chesapeake Bay’s numerous rivers, anchorages, and ports.

Portsmouth ≫ Chesapeake Bay

While cruising north up the harbor, we heard a warship warn a pleasure craft to stay at least 500 yards away. As we exited the James River into the Chesapeake, a warship moved toward us in the ship channel. We left the channel and kept our distance.

We arrived at the Regatta Point Yachting Center, formerly Dozier’s, in Deltaville, Virginia, at 2 p.m. after a 59-mile cruise.

An intense squall blew through on Sunday afternoon, with wind gusts of 50 mph for a sustained three minutes. Torrential rain followed. Thankfully, we were tucked safely under our satellite TV-blocking roof.

After spending a third night in Deltaville, we cast off at 9:15 a.m. on Monday. That night, we stayed at the Onancock town wharf. We cast off at 9:45 the following morning for Tangier Island, a 20-mile cruise from Onancock. We called Parks Marina to get a few hours’ dockage but gave up after several attempts and no response. Finally, we tied up to the marina’s face dock. Mr. Parks, the owner, had been working on his boat’s engine and did not see us arrive. He eventually charged us $5 to tie up.

Tangier, Virginia, on Tangier Island in the Chesapeake Bay, had a population of 727 when we were there. Most of the residents were watermen who made a living from crabbing, oysters and fishing.

After touring Tangier Island for a couple of hours, we had lunch at the Fisherman’s Corner. When asked for his recommendation, Mr. Parks suggested two restaurants and told us to choose. Since it’s a small island, he didn’t want to get into any feuds. However, he let slip that the two ladies at Fisherman’s Corner were hard-working, so we took that as a hint.

After departing Tangier Island, we cruised 46 miles up the Chesapeake and docked at the Solomons Harbor Marina, attached to the Holiday Inn.

When I met John, the harbormaster, he gave me a can of propane in case I wanted to cook on his grill and said the first two bags of ice were free. The Holiday Inn has a tiki bar, swimming pool, health club and restaurant. The area has several other restaurants nearby, most with dinghy docks.

Although we’d planned to stay only two nights at Solomons, I hinted to the harbormaster that we might stay longer because of the facilities. He offered us a 30% discount if we stayed four nights instead of two. Deal!

In addition to the swimming pool, health club, free ice and free propane, the Holiday Inn front desk hands out free happy hour drink coupons and provides appetizers. Why would we leave?

Chesapeake Bay ≫ St. Michaels, Maryland

Eventually, of course, we had to leave. And on Saturday morning, we cast off and cruised down the creek to the fuel dock. Then, after taking on 203 gallons of diesel, we headed out straight up the middle of the Chesapeake. We turned right at Eastern Bay and down the Miles River to St. Michaels, Maryland.

The area has several marinas with rates from $2 to $3.68 per foot. We chose St. Michaels Marina, the most expensive per foot plus $20 for electricity. However, we could see three restaurants from the slip with more located nearby.

During the War of 1812, the British fleet bombarded St. Michaels at night. As a ruse, the townspeople dimmed their lights and hung lanterns in the trees just beyond town so the cannonballs would overshoot, sparing the town. The plan worked, and St. Michaels became known as “the town that fooled the British.”

Now on day 265 of our America’s Great Loop adventure, we discover that we’ll cross our wake in Waukegan approximately one year from the day we departed.

In St. Michaels, we waited for the wind to calm down before casting off at 11 a.m. We had a wonderful visit, and I’ll miss their swimming pool and the insanity of the weekend warriors.

St. Michaels ≫ Annapolis and Baltimore, Maryland

After a flat cruise across the Chesapeake to Annapolis, we tied up along the long wall of the Annapolis City Dock, one block from the U.S. Naval Academy entrance and right in the middle of everything.

On a beautiful, warm sunny Saturday, we cruised 32 miles from Annapolis harbor to downtown Baltimore on a Chesapeake jammed with boats. Entering Baltimore harbor, we passed by Fort McHenry, which inspired Francis Scott Key to write “The Star-Spangled Banner.”

To celebrate Father’s Day, we caught an Orioles baseball game at Baltimore’s Camden Yards, only a short walk from the marina. The Orioles beat the Toronto Blue Jays 11–6 and won the three-game series 2­–1. Unfortunately, the ballpark was hotter than Hades, with dark green plastic seats that put you at risk for third-degree burns. Everyone who sat down around us cried out in surprise.

Baltimore ≫ Cape May, New Jersey

After three nights in Baltimore, we cruised 50 miles to spend the night at Bohemia River Yacht Club. Fellow Looper and unofficial AGLCA harbor host for the northern Chesapeake, Foster Schucker, stopped by for sundowners before driving us to dinner. His boat, Quo Vadimus, translates to “Where are we going?” His sister suggested the boat’s homeport of Nowhere, Oklahoma, though Foster had never been there.

The next day, we shoved off at 8:15 a.m. to catch a favorable tide on the Chesapeake and Delaware Canal. Only one short section of the C&D Canal has a no-wake zone, so we powered up and cruised through at 25 mph. The straight flat-water canal ends at the Delaware River, which in turn dumps into Delaware Bay.

The bay’s wide water proved a little lumpy on the beam. After we passed Miah Maull Shoal Light, we turned left and had the waves on the stern quarter, which flattened things out nicely. Once we entered the Cape May Canal, the water had gone dead flat again.

After an 82-mile cruise, we tied up at Utsch’s Marina in Cape May, New Jersey. Frequented by many Loopers, the marina gave us a goody bag with the coveted Utsch sweet red wine, three biscotti, and a bar of handmade soap.

Cape May ≫ Atlantic City and Brick, New Jersey

After two days at Utsch’s Marina, we departed on a 44-mile cruise to Atlantic City. We hadn’t been on the ocean since leaving Saint Augustine, Florida. Fortunately, the forecast conditions were favorable for an ocean passage.

As we cruised up the Atlantic Ocean, the flat seas started to build as we headed north, with 15 to 20 mph winds from the northeast. Waves had reached 2 to 3 feet by the time we arrived off Atlantic City. We watched a head boat (public fishing boat) come out of the inlet, turn around and go right back in.

On Sunday, Looper friends George and Pat Hospodar arrived at our boat at 8 a.m. George came aboard to guide us through Barnegat Bay and to their home dock. As Pat drove back home, we cruised 52 miles up the Atlantic coast past Little Egg Inlet to Barnegat Inlet at Oyster Creek Channel. Although George had warned us that Barnegat Bay got crowded on Sundays, nothing prepared us for the armada surrounding us as we entered the bay.

Dozens of boats were either anchored, drift fishing or blasting through the narrow channel, throwing massive wakes. Often three and four larger boats would speed past together.

Cruising north up Barnegat Bay, we turned into the narrow channel to George and Pat’s waterfront home, where they dock Reflection for the summer. They cruise back to Marathon, Florida, in October. Since their next-door neighbor, Ernie, recently sold his boat, we tied up in front of his house.

Brick ≫ New York City

After a two-day stay in Brick, we shoved off from Ernie’s dock at 9:30 a.m. and gave George and Pat a fond farewell and a hearty thanks for their excellent hospitality.

After a 10-mile winding course up Barnegat Bay in thin water, we passed through Point Pleasant Canal to Manasquan River and out onto the Atlantic Ocean. We anticipated winds from the south at 10 to 15 mph with gusts of 20 mph and up to 3-foot waves with an 8-second interval. But in reality, the seas were much flatter. As a result, it only took us an hour to cruise 25 miles from Manasquan Inlet to Sandy Hook.

Our next stop, Great Kills Yacht Club on Staten Island, was 48 miles away. New York Looper harbor host John Calascibetta made our reservation and met us at the dock along with a cast of thousands to take our lines.

Cruising America's Great Loop Part Six Great Kills Yacht Club on New York's Staten Island
Great Kills Yacht Club

The Great Kills Yacht Club has a fantastic business model. In 2016, it had 150 paid members at $400 per year, 25 legacy members (free after 25 years of paid membership), and 300 members on its waiting list, with more waiting for a spot. In 2016, a 40-foot slip at the club cost $750 per year. At the marina next door, a similar slip costs $7,000 per year.

We ended up at a low-floating dock, so we had to tie a swim ladder to the side to get off the boat. However, since the Looper on the end dock would be leaving the next day, we moved there, which meant we could climb on and off using our swim platform.

On Friday, we visited Manhattan. First, John gave us a ride to the Staten Island Railway Great Kills station. Then, we took the train to the Staten Island Ferry, the ferry to lower Manhattan, and the bus to the 9/11 Memorial.

On Saturday, we cruised to the Statue of Liberty alongside another Looper, Joe Pico, on his boat. Of course, we took pictures of each other’s boats in front of the Statue of Liberty.

New York City ≫ Troy, New York

Next, we cruised 50 miles up the Hudson River to Half Moon Bay Marina. On the way, we passed under the new Tappan Zee Bridge, which was under construction. Near the bridge, we saw tiny “No Wake” signs. Three police boats hid behind the bridge abutment. Not fooled, we transited without incident.

However, the pump-out system at the Half Moon Bay dock kept losing pressure, so it took us an hour to pump out both holding tanks. After entering our slip next to Looper friends on Moondance, Steve Plotkin, the animated marina owner, took our lines, and we plugged in.

This area features numerous sightseeing opportunities, including West Point, Franklin D. Roosevelt’s home, and the Culinary Institute of America.

After seven days, we had to leave. We paid $840 for the week, which included three days around the Fourth of July.

After a 57-mile cruise up the Hudson River, we arrived in downtown Kingston, New York, at 1:30 p.m. and tied up to the Kingston City Marina, which has nearby shops and restaurants to explore.

We enjoyed a spectacular view on the cruise up from Kingston to Troy, New York, with rolling green hills carpeting both sides of the Hudson River. In Washington Irving’s story, this is where Rip Van Winkle fell asleep for 20 years. Interestingly, we also passed Sleepy Hollow, New York, where Irving’s headless horseman rode.

Cruising America's Great Loop Part Six Transiting the Troy Lock in Troy, New York
Transiting the Troy Lock

Once we reached Troy, New York, we fueled up at the city dock before transiting the Troy Lock, our first lock since leaving Alabama’s Tombigbee Canal in November 2015. We retrieved and inflated the boat’s three orange teardrop fenders, which we’d stored in the boat’s basement.

During the 14-foot rise to Blackhawk River, the strong wind created a vortex in the lock chamber. A Canadian single-handing his 40-foot sailboat with its 50-foot mast strapped to the deck entered the lock ahead of us. What’s more, he didn’t tie up to the post until the lock doors were opening at the other end. As we entered the lock, the current blew and spun us around. After a few unsuccessful tries at tying up to the starboard wall, I gave up and tied to the port wall. Why fight it?

After passing through the Troy Lock, we entered Waterford, New York, the entrance to the Erie Canal.

In the next issue, we cruise through the Erie Canal, up the Oswego Canal, across Lake Ontario, and into Canada’s Trent-Severn Waterway.

John Simons

A member of Waukegan Sail & Power Squadron in District 20, John Simons has a USCG Masters License 100 ton. In his second career, he’s a broker for Weber Yachts, which sold Changing Latitudes two weeks after his Loop cruise. If you need help finding your ideal boat or selling your current one, you can email him.

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