There's no better way to take in the breathtaking beauty of coastal Maine than on windjammer cruises.
A trip aboard a historic Maine windjammer is to cast aside set itineraries and travel where the wind takes you. You'll cruise by uninhabited islands, lighthouses, and small towns only accessible by boat.
Recently, I embarked on a thrilling Maine sailing vacation aboard the Schooner J & E Riggin out of Rockland.
From the moment I stepped aboard the J & E Riggin, with its two tall masts and crisp sails, I was in another world. The language and customs of sailing ruled, and I had much to learn.
My windjammer cruise in Penobscot Bay, Maine, was more than just a pleasure ride—it was a chance to connect with nature, history, wildlife, and a community of like-minded travelers.
From the thrill of hoisting the sails to the serenity of anchoring in secluded coves, I'll take you through life's daily joys on a nearly 100-year-old sailboat.
You'll discover the unique charm of a schooner like the J & E Riggin (a National Historic Landmark), the crew's camaraderie, and the culinary delights prepared in the ship's galley.
So grab your sea legs and come aboard as we sail on a Maine windjammer cruise that's sure to inspire your next adventure!
Intro to Windjamming
But wait, what's windjamming? I was wondering the same thing when I received the generous invitation from the Maine Windjammer Association.
Windjammers are sailboats designed to take leisure travelers out on multi-day cruises. Some are older vessels that were originally built for other uses.
For example, the J & E Riggin is a two-masted schooner built in 1927 to function as an oyster dredger. It was named after its first Captain, Charles Riggin, and his two sons, Jacob and Edward.
As sailing gave way to more efficient means of powering cargo vessels, it was rebuilt to accommodate overnight guests.
However, the 120-foot-long, 61-ton J & E Riggin still has no inboard engine. It continues to rely on wind power, as originally intended.
When there's no wind, a 16-foot yawl boat with a diesel-powered engine pushes and navigates the schooner in and out of harbors.
This small but mighty motorboat also transports guests to and from land as needed.
Maine Windjammer Association
The Maine Windjammer Association represents “the largest fleet of traditional tall ships in the Americas.”
While each ship is “independently owned and operated,” all owners work together to promote windjamming in Maine.
The fleet features nine windjammers operating out of two home ports (Rockland Harbor and Camden Harbor) in Midcoast Maine:
- Schooner American Eagle (Rockland)
- Schooner Grace Bailey (Rockland)
- Schooner Heritage (Rockland)
- Schooner J & E Riggin (Rockland)
- Schooner Ladona (Rockland)
- Schooner Stephen Taber (Rockland)
- Windjammer Angelique (Camden)
- Schooner Lewis R. French (Camden)
- Schooner Mary Day (Camden)
A 10th, the three-masted Victory Chimes, was decommissioned in 2022 and sold at auction in 2023.
It was acquired by two brothers in New York City who've built a business on turning old boats into floating restaurants.
Arriving in Rockland
Thanks to the Maine Office of Tourism, I was afforded a comfortable night at the LimeRock Inn, a lovely B&B within walking distance from the town center.
Cruise passengers are asked to arrive at the J & E Riggin, docked at Windjammer Wharf, between 5 and 6 p.m. on the first day.
The night before we left, I had a fantastic farm-to-table dinner at Primo.
Then, on the day of departure, I used my free time to explore Rockland's museums and harbor. I also picked up last-minute items at Maine Sport Outfitters, including binoculars and rain gear.
Downtown Rockland is walkable, which is helpful because rideshare services don't operate there. However, two local taxi companies are available if you need help.
Maine Sip & Sail Cruise
Throughout the cruise, we'd be sampling craft beers and ciders made in the state and stopping at two local breweries.
Day 1: Boarding the J & E Riggin
A few minutes before 5 p.m., I rolled my luggage from the B&B to Windjammer Wharf. Given the small cabins, a duffel bag or backpack is the preferred choice for sailing.
But I had to pack for a wedding in Boston, so they weren't an option. Having a carry-on size piece of luggage was manageable, but I'd avoid it.
Soon after I arrived, Captain Justin Schaefer pulled into the parking lot. We'd met a few months earlier in Portland at AdventureELEVATE, a travel conference I attended.
He introduced me to his wife and co-owner of the J & E Riggin, Captain Jocelyn Schmidt. They each have a 100-ton captain's license. However, Jocelyn's primary role now is that of chef.
Captain Justin carried my luggage down the dock, and I boarded my first windjammer cruise in Maine.
I was shown to cabin #3 in the front third of the boat. Getting down to all the cabins requires stepping backward down a near-vertical ladder. Luggage is best passed down from one person to another.
Inside my cabin were two single beds with mattresses, clean sheets, blankets, quilts, and towels. There was one ceiling light and a small window that could be opened a few inches.
Every cabin has a sink with fresh water. The cabins in the front of the boat have plumbing that requires guests to tap on a plastic pedal on the floor to drain water.
It's a bit laborious, though it encouraged me to use the clean water efficiently to brush my teeth and wash my face. A shelf provides space for toiletries, and there's a little mirror on the wall.
Each bunk has a reading light and shelf for storage. Since Kel couldn't join me for the cruise, I used the extra bed to lay out my clothes.
Two USB ports are available to charge electronic devices like cell phones, and a 12V outlet is helpful for CPAP machines (for guests with sleep apnea).
If you're a CPAP user like me, you must buy a 12V adapter to work with the outlet. I paid $40 for one on Amazon.com, and it worked fine.
Additional items provided in each cabin include a small LED flashlight and a padded, stadium-style seat for use on the main deck.
The tight quarters are a part of the windjamming experience. The schooner is anchored in the evenings, so you're not trying to sleep while on the move.
Now that you've seen where I slept for four nights, you might be wondering about the bathroom situation.
The J & E Riggin has two toilets. They're called “heads” in sailing speak. Both heads are on the main deck, adjacent to each other. These small bathrooms feature toilets that require a little manual labor.
First, you do your business. Then close the lid and pump the lever 10-12 times until it hisses. Lift the top, and if everything is gone, your work is done. If not, you have to repeat the process.
If, after multiple tries, it's still not clear, you're encouraged to notify a crew member, who, much to their credit, will take care of it. Additionally, the heads are cleaned three times a day.
The toilet paper is thin since these sailboat toilets are a bit sensitive. And you're asked only to use 6-8 squares to reduce the odds of them clogging.
One of the heads also features a handheld shower. Showers can only be taken while the boat is anchored, which is to say after breakfast but before setting sail or after it's anchored (up until 10 p.m.).
Crew members made hot water available for those wanting a shower. I didn't bother, choosing to wash my face regularly and double up on deodorant instead. Chalk it up to this unique travel experience.
You won't be alone, and nobody on windjammer cruises in Maine will judge you for it.
Dinette and Galley
Weather permitting, most meals are served on the main deck. But there's also a galley and dining area below deck.
Thankfully, we only had one meal in this room (lunch on the first day as it was drizzling). It was a tight squeeze, and you immediately missed the views and breeze.
Old photos of the J & E Riggin and recent plaques from friendly races with the other Maine windjammers decorate the space. Some books about sailing and Maine are available as well.
Anchoring the kitchen is a large, black wood-burning stove named Lucy. It looks formidable, and I was surprised to learn there's always a fire burning, even while sailing and sometimes overnight.
For safety reasons, a crew member is always awake on the boat, including in the wee hours of the morning. As you'll soon see, the galley crew can create some epic meals here.
At 6 p.m., there was a Captain's Call after all the guests loaded their luggage on the schooner.
He introduced himself, Jocelyn, and their experienced crew, which included:
- Alex, the First Mate (a supervisory role)
- Elias, the Deckhand (who does what Alex asks)
- Keegan, the Galley Hand (who assists Jocelyn with the cooking)
- Nancy, an Apprentice (who was a passenger the previous year)
- Jenny, the Social Media Manager (and who helps with other tasks as needed)
We learned how to use the heads and when we could shower. And guests Guests to keep noise levels down from 10 p.m. to 7 a.m.
Then, Justin set us free to grab dinner in Rockland. We'd return afterward and spend our first night aboard the J & E Riggin at Windjammer Wharf.
Day 2: Sailing to New Haven
The next day, I was up at 6:30 a.m. The coffee and hot water for tea and hot chocolate were set out for guests on the main deck. It was 63 F and chilly, with light rain and heavy fog blanketing the harbor.
At 8:15 a.m., a bell on the main deck rang, indicating that breakfast was ready.
Buttermilk pancakes with Maine maple syrup, blueberry syrup, whipped cream, lemon curd, and fruit toppings were available. Plus, bacon, homemade granola, Greek yogurt, and fresh fruits.
As this first breakfast would attest, we wouldn't go hungry on this cruise. There would always be delicious meals, and usually, enough for guests to get seconds.
After breakfast, guests made last-minute purchases in town. Then, those with cars paid $20 each for parking passes.
The First Mate, Alex, gave a safety presentation at 10:45 a.m. where she pointed out where to find life preservers, life rings for anyone who falls overboard and fire extinguishers.
Leaving Rockland Harbor
The schooners depart the harbor as they're ready. Captains communicate when they're heading out, but there are no specific times for each ship to leave.
One by one, they slipped away from the dock. First, the Stephen Taber. Then Grace Bailey. She was followed by the white-hulled Ladona, which has a motor.
Around 11 a.m., the J & E Riggin departed, too. Our yawl boat was used like a mini-tugboat to pull the traditional schooner away from the dock, turn it around, and then push it out of Rockland Harbor.
Given the low visibility, I was amazed at our Captain's ability to steer the 61-ton schooner out of the harbor. Dozens of anchored sailboats were barely visible amid the thick haze.
When we passed the Rockland Breakwater Lighthouse, we could barely see it. The mile-long breakwater built to connect it with land disappeared in the mist.
Raising the Sails
It was 11:30 a.m. when we passed the lighthouse, and the call was given for volunteers to help raise the mainsail. Guests of all ages lined up on the schooner's port (left side) and starboard (right side).
The crew members called commands as each side pulled the rope to raise the 1.5-ton (3,000-pound) mainsail and top beam.
The number of people helping and the built-in mechanical advantages make it doable. Helping out is voluntary, but often, guests enjoy this aspect of their Maine windjammer cruises. I did.
Once the mainsail was raised, the crew and guests raised the three other sails, each requiring less effort and people than the one before it.
Despite playing a small part in raising those sails, I felt proud every time I looked at them.
As we began sailing, I asked the Captain about the gear he used to navigate. He walked me through it all, pointing out the radar and radios.
One device I found interesting notifies him of the closest vessel and how long it would take for the J & E Riggin to intersect with it if both boats remained at the same speed and heading.
Not long after the sails were raised, we went below deck to the dinette for our first lunch together.
Jocelyn and her Galley Hand, Keegan, had prepared New England clam chowder and strawberry and goat cheese salads.
Fresh-baked biscuits were served with salted butter and honey from Jocelyn's apiary (bee hives). And delicious candied ginger shortbread was served for dessert.
Given the theme of our windjammer cruise was Maine craft beers, everyone could try two beers with every lunch and dinner for the entire trip. On a few occasions, a cider was offered instead of a beer.
Once lunch wrapped up, I returned to the main deck, where I caught a glimpse of the dark red sails of the Windjammer Angelique off the port side.
By 2:30 p.m., we were passing along the north coast of Vinalhaven Island, where we could see Browns Head Light Station and lobster boats at work.
Fifteen minutes later, the crew dropped the iron anchor off the port side. The one on the starboard side, we were told, was a “storm anchor” and is not routinely used.
North Haven Brewing Co.
Captain Justin began ferrying us to North Haven Island using the yawl boat. It was only a minute's walk from the dock to Calderwood Hall, a community center home to North Haven Brewing Co.
The Maine microbrewery opened in 2017 after friends Ben Lovell and Jesse Davisson took their homebrewing hobby to the next level. Ben's sister, Elizabeth, is a co-owner.
Ben and Jesse are fishermen, and their interest in beermaking came about when they had downtime every winter during the off-season.
As part of our Sips and Sails-themed cruise, each guest on the J & E Riggin was entitled to a beer flight.
The brewers invited us each to pick three of the four beers we wanted to sample, with the fourth being their signature Keeper IPA.
I liked the Keeper and Swell beers. The Spark Plug had strong coffee and chocolate flavors. And the Barrel Stove was my least favorite.
North Haven Brewing Co.'s beers are only available at the brewery, which they said provides enough demand to keep them busy. A ferry from Rockland offers regular service to the island.
Back on the J & E Riggin, we were welcomed with iced oysters from John's River.
Four salt options were provided, a mignonette, a sliced French baguette from Atlantic Baking Company (Rockland), and three kinds of compound butter.
Dinner followed an hour later, at 6:30 p.m. Lemon and white wine poached Atlantic salmon was served with lemon risotto, butternut squash, tomatoes, and roasted garlic scapes. The fish was excellent.
But wait, there's more! Homemade strawberry rhubarb pie with hand-whipped cream was provided for dessert. What's a little rain and fog when you're fed like royalty?
Day 3: Sailing to Waterman Point
I awoke several times on my second night aboard the J & E Riggin. However, I was always able to drift off quickly again. At 7:30 a.m., it was time to rise and shine. I got dressed and climbed up to the main deck.
I made hot chocolate and indulged in a second serving of strawberry rhubarb pie.
Jocelyn told me guests are likelier to eat the leftover dessert when placed out the following day. And she was right!
For breakfast, a North African tomato-based dish called shakshuka was served with avocados, olives, capers, and Greek yogurt. A tasty rosemary focaccia and lemon poppy seed muffins were also available.
Raising the Anchor
At 9 a.m., the crew began removing the tarp over the main deck. A guest pointed out a harbor seal swimming through the calm waters. Soon, the fog would clear, and visibility would increase.
We raised the mainsail and second one as well. Then, the crew, with the help of some volunteers, worked together to pull up the 500-pound iron anchor, a strenuous task.
For example, one person's job was to lay the heavy iron chain back in the storage box in an organized fashion.
Once the anchor was up, the J & E Riggin glided forward as the crew secured the anchor to the boat's port side and raised the smaller sails.
We saw blue skies for the first time since boarding the J & E Riggin, and everyone was appreciative. My priorities changed from staying warm and dry to wearing enough sunblock.
Since we sailed out of the channel separating North Haven and Vinalhaven islands the same way we'd entered the day before, we got a better look at the scenery.
This included Browns Head Light Station, many beautiful vacation homes, and Fiddlers Ledge, a pillar that marks the end of an underwater ledge that juts out from North Haven island.
Here, sailing at a leisurely 3 knots, we could hear the ringing of a red buoy that marks the entrance to New Haven harbor.
When I asked Captain Justin about top speeds, he said the Riggin hit 10 knots (11.5 miles per hour) during The Great Schooner Race the week before.
He said they begin to take the sails down at 12 knots (13.8 miles per hour).
As we cruised west across West Penobscot Bay toward a brewery on the mainland, the wind died, and we began using the yawl boat to push the mighty schooner. Without the help, we wouldn't move.
Around noon, we passed Owls Head Lighthouse, at which point we began cruising south down the Eastern Seaboard.
This 30-foot lighthouse was built in 1825 and can be visited on foot via Owls Head State Park.
Lunch was pulled pork shoulder cooked overnight with scratch-made brioche buns and a housemade BBQ sauce. Gouda and cheddar cheese were available as toppings.
The sandwiches were served with sides of sweet potato hash and cole slaw. For dessert, carrot cake cupcakes. Yum!
Waterman's Beach Brewery
At 2:30 p.m., the crew dropped anchor off Waterman Point, and the Captain began ferrying us to shore for our second brewery visit.
Waterman's Beach Brewery is a true Maine original. Before the building housed brewing equipment, it was a family-owned lobster shack for 30 years.
In 2001, Waterman's Beach Lobster Shack won the America's Classic Award from the James Beard Foundation.
By 2016, the owners were ready to retire. That's when Heath Curtis, a scallop fisherman, came up with the idea to turn his mom's lobster shack into a craft brewery.
Three years later, with the help of Brad Frost, co-owner and head brewer, and Brad's wife Anna, the brewery opened.
Everyone had the chance to try four beers, so I chose:
- Crown to Coast Kolsch Style Ale
- Loowit Session Ale
- Sonic Temple Pale Ale
- Polka Party (a smoky beer)
My favorite was the Sonic Temple, followed by Crown to Coast.
Captain Justin announced we could order not one but two pints of our favorite beer. As my fellow passengers and I were sampling the beers and enjoying the beautiful ocean view, the J & E Riggin's crew prepared a lobster bake on the beach.
I'm not a huge beer drinker, but it wasn't hard to keep up, given the weather and scenery.
First, they set a fire and began grilling corn on the cob. Potatoes were wrapped in aluminum foil before being placed near the fire.
Then, the live Maine lobsters are added to a metal bucket with one inch of salt water. They're covered with kelp found along the beach and steamed for about 20 minutes.
As if that wasn't enough, they also grilled two steaks! We were in for an authentic surf ‘n turf dinner.
I experienced my first lobster bake in Portland the week before. However, this one was much more intimate.
The brewery opened on their day off just for us and gave permission to have the lobster bake in their front yard. It demonstrated a sense of community among Mainers.
To cap off our fantastic sunset dinner at an oceanside brewery, the Captain and crew made ooey-gooey s'mores tacos over the campfire.
Once everything had been packed up, we left the beach and brewery as we'd found it. Justin shuttled us back to the J & E Riggin, its mainsail glowing in the fading sun.
It would be hard to beat our third day of the Maine windjammer cruise, but Mother Nature had a few surprises in store for us.
Day 4: Sailing to Vinalhaven
After a few days at sea, I became accustomed to the schooner's schedule and routines. Morning coffee, delicious breakfast, raise the anchor, raise the sails. It was all feeling more comfortable.
Before we set sail from Waterman's Point, the crew set up the ship's chandlery, aka the gift shop.
Since several couples on the windjammer cruise had sailed with the Riggin before, they could attest to the quality of the clothing.
Impressed by the pricing, I bought a magenta hat for $22 and a green embroidered T-shirt for $25. I began wearing the cap immediately.
Raising the Anchor
At 9:50 a.m., after packing the shop and cleaning the breakfast dishes, I helped Nancy and Keegan pull up the anchor.
Using the proper technique and throwing your body weight into the movements makes a huge difference.
I learned you don't have to be super muscular to do this stuff. The proper technique, teamwork, and the mechanical advantages of the riggings go a long way.
Gloves aren't worn as they can get caught in the ropes. You also don't want to rely on putting gloves on in an emergency. I was told using your bare hands and building calluses is better.
Ten minutes later, we cruised with a cool breeze, looking for lighthouses and marine life.
The Captain planned to sail south along the rugged Maine coast and east toward Matinicus Island. We'd then head north to anchor in a secluded cove on Vinalhaven Island.
First, we passed Sprucehead Island and some huge and attractive waterfront homes. I helped raise the mainsail as we passed Whitehead Island Lighthouse. A harbor seal was spotted popping its head up.
Further south, we could see Tenants Harbor Lighthouse and the home of Jamie Wyeth on Southern Island.
The island is private property, and Jamie Wyeth, an artist like his renowned father, the painter Andrew Wyeth, lives there full time.
Minutes later, I spotted a porpoise coming up for air off the starboard side. And an hour later, three porpoises were seen off the port side. A group of porpoises is known as a gam.
Lunch on this lovely day consisted of lobster bisque made with leftover lobster from the previous night, rolls, salad, and luscious lemon bars.
During lunch, as we cruised east past Little Green Island, we spotted the first of several fin whales, the second-largest whale species on Earth.
Their small dorsal fin belies their massive size. Fin whales can weigh between 40 to 80 tons (80,000 to 160,000 pounds) and grow to 85 feet in length.
To put that in perspective, an average 60-ton fin whale would weigh as much as Schooner J & E Riggin.
The fin whale population suffered greatly during a period of mid-19th-century whale hunting. Today, they are endangered. Their average lifespan is 80 to 90 years.
Everyone on board the J & E Riggin was excited by the spotting, including Justin, Jocelyn, and the crew. The Captain immediately called the team to make adjustments and slow us down.
I had asked Justin about the potential for us to see whales before we got underway on Day 1. My expectations were low after hearing whale sightings were possible but not routine.
Luke, a passenger with 30 years of experience on Maine windjammer cruises, said he'd only seen whales three times.
The fine whale(s) we watched surfaced a dozen times before we continued east past Large Green Island.
For about 45 minutes, we seemed to see all the wildlife at once. There was a seal spotting and enough fin whales that we were getting used to their presence.
A baby shark near the schooner led to crew members breaking out in song and dance. And porpoises and a pair of puffins were also seen—my investment in binoculars paid off.
As we approached Matinicus Island, one of Maine's most remote inhabited islands, we turned north toward Vinalhaven.
We cruised past Heron Neck Lighthouse at the southern tip of Greens Island and through Hurricane Sound until we arrived at a quiet cove. The Captain said we'd sailed 30 nautical miles during the day.
The crew dropped anchor and began prepping the Savannah, a cat ketch rig carried by the J & E Riggin.
We had the cove to ourselves, save for a larger sailboat already anchored there when we arrived. Within an hour, though, we were joined by the Schooner Stephen Taber.
As appetizers were brought to the main deck, the Captain took a few passengers out on the Savannah for a sunset sail.
I enjoyed the perspective it gave us of the schooner and that it was a quieter ride than the yawl we'd used to visit the breweries.
At 6 p.m., a passenger spotted a bald eagle on a tree top on Turnip Island. The eagle was close enough to see clearly with binoculars, which was exciting. It was the first adult bald eagle I'd seen in the wild.
Twenty minutes later, tender beef brisket was served on the main deck, with polenta and Brussels sprouts.
As it was our last night, we got to choose what to drink. I picked the Bar Harbor Blueberry Ale by Atlantic Brewing Company.
Dessert was an excellent cheesecake with salted caramel drizzle, which we ate while watching the colorful sunset.
Captain Justin left the mainsail up overnight, so we'd have less work to do on our last morning.
Day 5: Return to Rockland
On the fifth and final day of our Maine windjammer cruise. The water was so still it created a near-flawless reflection of the Stephen Taber.
I felt grateful to have such a beautiful setting to myself, if only for a few minutes.
The morning dew coated the seating areas, so I stayed on my feet, gingerly walking around the main deck and shooting photos.
At 5:45 a.m., Keegan brought the coffee and tea out. Jocelyn and Justin were also already at work. A few people were also awake on our neighbor, Schooner Stephen Taber.
Jenny's grandparents previously owned the Stephen Taber, and her uncle owns it now.
Around 6:30 p.m., a tray of coffee cake was placed on the deck. Soon after, a bald eagle was spotted in a tree on Hall Island in front of us. Using binoculars, I was also able to see the eagle's nest, too.
Breakfast was homemade NY-style bagels with lox (smoked salmon) and other toppings. Scrambled eggs, cantaloupe, and kiwi were also provided.
Our Final Sail
The Stephen Taber sailed off before us. I didn't mind, as it gave me a sense of what the J & E Riggin looked like when cruising. By 8:30 a.m., we were sailing too.
It was a short and bittersweet ride back to Windjammer Wharf in Rockland Harbor. I'd spent the cruise making new friends, learning sailing vocabulary, and being fed like a King.
I'd gotten the hang of spending days and nights at sea and been spoiled by the appearances of fin whales, porpoises, seals, puffins, and bald eagles.
Taking a Maine windjammer cruise was the adventure at sea I didn't know I needed. As we entered Rockland Harbor, the Rockland Breakwater Lighthouse, shrouded in fog at the start of our trip, was visible.
The Captain switched to using the yawl boat to guide the J & E Riggin back to its safe harbor. We glided past dozens of sailboats that were barely visible on our first day.
And then we slid along the dock, the crew throwing ropes to secure the schooner. The disembarkation happened quickly, signaling the end of the trip.
People had planes to catch, including me. The crew had their work cut out for them, needing to turn over the sailboat in 24 hours.
The following day at 5 p.m., the J & E Riggin was due to depart on a 3-night Kids & Family Cruise.
Guests were provided envelopes in their cabins for tips, and a 5 to 10% gratuity is recommended.
One hundred percent of the tips go to the working crew (everyone besides the owners, Justin and Jocelyn). From everything I saw during my 4-night windjammer cruise, they deserved it.
My experience aboard the J & E Riggin showed me firsthand why these historic ships have so many repeat customers.
The Maine windjammer cruises are a unique opportunity to sail tall ships amid stunning scenery.
Throw in friendly and approachable owners like Captains Justin and Jocelyn, an earnest and experienced crew, and lots of good food, and it has the makings for a wonderful vacation.
Thank you to the Maine Windjammer Association and J & E Riggin for inviting me to experience one of their cruises at no cost. My night at the LimeRock Inn was organized in partnership with the Maine Office of Tourism.