Virtual Cruise of the East Coast: Portland, ME

This small city has New England charm and is home to weathered salts and urban hipsters alike.

Move your cursor over the chart to see resourse information for Portland.

Three months after leaving our home port of Annapolis, Maryland, we arrive in Portland, Maine, the perfect staging area to begin the Down East leg of our one-year, virtual cruise. Ideally, we’ll want two months to explore Maine’s most popular ports and anchorages, and July and August are the best for warm days, cool evenings and moderate winds (in the mornings at least).

It’s also the time of year when heavy fog often rolls in, so we’ll have to be prepared to stay put for a bit, we hope in harbors with a variety of things to do. Along with dodging lobster pots, fog is just part of the Down East experience.


After our enjoyable visit to Plymouth, Massachusetts, we stop in Portsmouth, New Hampshire, for a couple of days, and from there we have a 60-mile run up the Atlantic Coast before arriving in Portland late in the afternoon. This route takes us three to five miles offshore as we head northeast, first rounding Kennebunkport and Cape Porpoise and then Cape Elizabeth before turning north. We spot the iconic Portland Head Light off our port bow and follow the marks into the busy harbor. Freighters, cruise ships, tugs, commercial lobster boats, tour boats and fast ferries seem to be coming and going in all directions.

As we cruise along the shoreline of the Fore River, with Old Port on one side and South Portland on the other, we first pass the mooring field managed by Portland Yacht Services and then the row of megayachts docked at DiMillo’s Old Port Marina. My wife, Stacey, spots something small moving in the water dead ahead and fears it’s a dog that fell overboard. Changing course to get a closer look, we are relieved to see it’s a seal, welcoming us to Portland. Seal or dog, this busy harbor is no place for a leisurely swim.

During past visits we’ve learned that things can be a bit hectic and noisy on the north side of the harbor, so this year we decide to get a slip at Sunset Marina in South Portland. Tied up along the 500-foot floating dock with our bow toward the chop stirred up by harbor traffic, we have a great view of the bustling harbor and the city’s signature skyline.


After a late lunch at the Saltwater Grille, the marina’s excellent on-premises restaurant, we walk along the waterfront to Bug Light Park and Spring Point Marina, part of the Port Harbor Marine group. With more than 250 slips and room enough to handle yachts up to 200 feet in length overall, this is another alternative to staying in Old Port.

The next morning we take a short taxi ride to Old Port. Although Sunset Marina has a dinghy dock, and it’s possible to cross the harbor channel in a decent-size tender, such an adventure has been likened to “making your way across an active airport runway on a tricycle” by the late, noted sailor Dodge Morgan. (We’ll later anchor off Morgan’s home port, picturesque Snow Island.) We also discover several water taxis that run between the two sides of the harbor as well as to outlying islands.

Portland is a city of contrasts. On one hand, it remains a major shipping port and commercial fishing center. On the other, it has thrived in its transition from its past legacy as a shipbuilding and exporting hot spot to a modern city with an active arts community, reclaimed Victorian neighborhoods inhabited by young professionals, and cobblestone streets lined with five-star restaurants and chic boutiques.


Commercial lobstermen and yachtsmen share downtown dock space, and weathered New England salts seem to coexist with trendy, Tweeting hipsters. Even Portland’s size suggests contrast. It is Maine’s largest city and the metro area’s population is 250,000, yet it somehow has the feel of a much smaller — even quaint — New England town. Old waterfront warehouses and the former Bath Iron Works facility have been renovated and transformed into a vibrant shopping, office and restaurant district, providing a charming connection between old and new.

Stacey, an art teacher and water colorist, suggests we first visit the Portland Museum of Art, which houses more than 17,000 works covering three centuries. Here we see pieces by American artists Winslow Homer, Louise Nevelson, John Singer Sargent, Andrew Wyeth and many others. European movements are represented by Degas, Monet, Picasso, Renoir and more. We are among the first to take a 2½-hour guided tour of the Winslow Homer Studio, which departs from and returns to the museum three times a day.

My wife knows my limited attention span for museum visits, so for a change of pace we search out the hard-to-find Novare Res Bier Cafe for lunch. Hidden in an alley off Exchange Street, this little treasure, which translates from Latin to “A New Thing,” offers a 20-page beer menu, good bar food and a cozy outdoor patio.
It’s soon time to walk off the pints of Belgian brew, so we embark on a guided tour of the Portland Observatory, which takes us to the top of an 86-foot wooden tower overlooking the harbor. In operation since 1807, the observatory became a National Historic Monument in 2006. We can imagine its founder, Capt. Lemuel Moody, peering through his telescope and communicating with ships in the harbor by signal flag. On a clear day, this shouldn’t be missed.


Topping off our day of sightseeing, we follow the interactive “Old Port Tour Map” created by Greater Portland Landmarks. The map provides the location and history of more than 20 prominent buildings in the historic district. Much of the 19th-century architecture remains even after the infamous Great Fire of 1866 destroyed a good part of the commercial district and left 10,000 people homeless. Now a mixture of condos, apartments, offices, shops and restaurants, it comes alive during summer evenings. Since it happens to be Thursday, we are treated to a free concert held from 5 to 7:30 p.m. in Monument Square.

Our day of art appreciation, walking tours and concert-going comes to a grand finale with dinner at Street & Co. on Wharf Street. After forgetting to make a reservation, we wind up sitting at the bar, where we follow the friendly bartender’s superb recommendation of grilled lobster over linguine.

The next morning we awake under a heavy blanket of fog and realize that we’re going nowhere for the next several hours, at least. We can barely see the bright-yellow ferries in the harbor — although we can hear them — and the shoreline of Old Port is completely obscured. We take advantage of this downtime to walk to Hannaford Supermarket in the Mill Creek Shopping Center for some provisioning. With more groceries than we can carry, we take a taxi back to Sunset Marina and see that the fog hasn’t lifted. It looks like the perfect time to catch up on some boat-maintenance chores and our summer reading.

Saturday morning brings more fog, but the forecast for an afternoon clearing looks promising. Glad that we’re “stuck” in a port with so much to see and do, we take a taxi to see the Portland Head Light in Fort Williams Park on nearby Cape Elizabeth. This famous light was first lit in 1791 with 16 whale-oil lamps, and today the new light and foghorn are maintained by the U.S. Coast Guard.

Returning to our boat, we find the fog is finally lifting, and we leave Sunset Marina eager to head Down East and explore more of Maine’s fascinating coast.

Exploring Down East
After three days in Portland, Maine, our virtual cruise continues as we explore five of our favorite Down East locations.

Snow Island 43° 48.93′ N 69° 54.60′ W
The fog in Portland finally lifted enough in the afternoon for us to continue our cruise. Heading south into Casco Bay we round Cushing and Ram Island and then head up to the entrance to Quahog Bay, 12-miles from Cape Elizabeth. While the fog has lifted, we now find ourselves dodging hundreds – probably thousands – of lobster pots. Our vessel is equipped with shaft mounted spurs designed to cut away any lines just in case we accidentally run over a buoy. We arrive at Snow Island and drop our hook near the islets to the east. This little piece of paradise is where the late Dodge Morgan, the first American to sail solo nonstop around the world in 1986, made his home. Years before his death, we anchored here where one of his beautiful wooden schooners was moored. Our dog needs to find a spit of land, so we take our dinghy to one of the islets, where we sit and watch the sun go down on this idyllic, secluded anchorage.

Boothbay Harbor 43° 50.90′ N 69° 37.61′ W
Anxious to see a quintessential Maine village, we run 20-miles, rounding Cape Small and the Cuckholds before heading north into Boothbay Harbor. Carousel Marina is spotted to starboard as we make our approach, so we raise them on our VHF and get a slip assignment. With a fuel dock, on premises restaurant and an easy walk into town, this turns out to be a good choice. After crossing the 1000-foot long footbridge on the way to town, we find the perfect Maine village complete with shops, restaurants, pubs, art galleries, a hardware store, antiques, grocery stores and banks. Condos, inns and 18th and 19th century homes integrate seamlessly into the commercial scene. Referred to as the “Boating Capital of New England,” we admire the beautiful, classic yachts moored in the harbor, including a couple of Friendship sloops. With a calendar full of events and festivals, the village knows how to celebrate its maritime heritage.

East Boothbay 43° 52.00′ N 69°34.96′ W
Less than 10-miles away by sea, we stop at Ocean Point Marina in East Boothbay, where years ago we had major work done on our boat. Located on the Damariscotta River, there’s not much of a town here, but what there is is wonderfully charming. Besides the boatyard and post office, there’s the Lobsterman’s Wharf, where you need a fork to eat the “chowda.” And don’t miss a visit to the General Store just down the road for great sandwiches and pastries. If you would like to see some of the very finest craftsmanship in the world, ask for a tour of nearby Hodgdon Yachts, where legendary yachts have been built for five generations. Some of today’s most luxurious and classically designed yachts, including the 98-foot Windcrest and 155-foot Scheherazade have been built here.

Seal Cove 43° 53.17’N 69° 34.07′ W
If there is such a thing as a 5-Star anchorage, Seal Cove is it. It’s a bit tricky getting to it, but it’s worth the trouble of dodging lobster pots and using extra caution in avoiding the surrounding rock ledges. From East Boothbay, we head up the Damariscotta River between The Narrows, threading the green can “11” and red nun “12”, which can sometimes be awash in the wicked current. Rounding Hodgsons Island, we stay in the middle and drop our hook .75 miles inside to the east of a tiny islet and cove and south of another islet and long ledge. It’s best to enter here on a rising tide, about an hour after low tide, so that the ledges are visible. We’re surrounded by deep woods, a few private homes and only one or two other boats. Launching our dinghy, we land on Hodgsons Island and find a trail that we follow through the woods and along the shoreline. Later in the afternoon, we hail a local lobsterman returning from working his traps and buy two big, meaty lobsters that we steam for dinner. This must be boating heaven.

Monhegan Island 43° 45.87′ N 69° 19.35 W
There are two ways to get to Monhegan Island, located 10-miles in the ocean off Port Clyde – you can take your own boat and hope to find an empty mooring in the small harbor, or you can take a tour boat from Port Clyde. We pick up a mooring in Port Clyde, and early the next morning we take a ride on the 65-foot Laura B, which has been delivering passengers, freight and mail to Monhegan for the past 50 years. Arriving an hour after our departure we see that space is very limited in the small harbor, so we’re glad we left our boat in Port Clyde. The landing wharf is a center of activity as passengers with luggage are met by pickup trucks taking adventurous vacationers to their inn. We head out to find the rugged trails that cross the island and follow the high cliffs overlooking the ocean. It seems everywhere we look we see artists with their easels under the shade of their umbrellas, trying to capture the spectacular scenes as Jamie Wyeth and Rockwell Kent did years ago. After spending a good part of the day hiking and gazing at the incredible views wee head back to the wharf to get the last boat ride of the day back to Port Clyde. Resting our tired legs, we start planning the next leg of our one year, virtual cruise along the East Coast.