Finding Comfort and Camaraderie on a Maine Windjammer Cruise

View from the bow of the J & E Riggin Windjammer Cruise in Maine. -Windjammer cruise in Maine-715620180706

Except for the gentle lapping of water against the hull, all is quiet and I am as content as I could ever hope to be. I’ve spent the afternoon dining on lobster with new friends, on a deserted beach no less, and now we’re being treated to a beautiful sunset.

Susan Land, another guest — apparently the only one not in the grip of a food coma — begins to sing America the Beautiful. Did I mention it’s the Fourth of July? Inspired, the rest of us chime in and before you know it we are three songs into a medley of patriotic hits. Then someone suggests Bohemian Rhapsody and all hell breaks loose.

“Scaramouch! Scaramouche! Will you do the Fandango?!” Forgetting all but a few lyrics, we sing whatever springs to mind at the top of our lungs.

“Thunderbolt and Lightning, very very frightening!”


Greg Shannon, also a guest, grabs his phone, Google’s the lyrics then shouts them line by line for us to repeat. By this time, the absurdity of this performance has me laughing so hard, I can barely breathe. Bent over in stitches with 25 passengers and crew, it’s hard to believe that just a short time ago I didn’t know any of them at all.  

(To pause the slideshow, hover your mouse over the image)

My windjammer cruise in Maine began three days earlier in Rockland, (a classic coastal town with a Hallmark card Main Street and a multi-generational lobster industry) when I boarded the J & E Riggin, a sleek, 11 cabin, 120-foot, landmark wooden schooner built in 1927.

Originally designed as an oystercatcher, it’s one of a dozen or so historic boats in the area dubbed windjammers that offer travelers a ship’s eye view of scenic Penobscot Bay.

My hosts Annie Mahle (a veteran chef and cookbook author) and Jon “Cap” Finger, co-captains in work and in life, have been offering eco-friendly Maine windjammer cruises for more than two decades. Their daughter Ella (18), one of two, is one of the six-member millennial crew.

Buffet dinner on the J & E Riggin -Windjammer cruise in Maine-521520180702
Poached salmon with nectarine and pepper salsa, quinoa (fried garlic, chives,), roasted beets over cauliflower over swiss chard drizzled with reduced balsamic. Seedy bread. For dessert: Black forest shortcake with brandied cherries and black biscuit with fresh whip cream

I am one of 18 guests, half of whom are “Riggin Relics”, a nickname given to passengers who’ve sailed three times or more. Dotty and Jon Craig from Connecticut tells me they’re celebrating their 16th voyage. Why do they keep coming back again and again?

I’d soon find out. 

Guests relax on the J & E Riggin on Penobscot Bay - Windjammer cruise in Maine-694220180704
Just chilling

It’s early morning and I’m tiptoeing across the deck doing my best not to wake the crew still snuggled in their sleeping bags. A lobster boat on its way to open water glides slowly past our boat to keep noise at a minimum. But as soon it hits the bay, the engine revs and “Jet Airliner” by the Steve Miller Band blasts from the ship. So much for quiet. 

Annie Mahle cooks on the J & E Riggin - Windjammer cruise in Maine-726020180707
Annie cooking two kinds of frittata: fontina, and scallion and bacon, served with zucchini and potato pancakes, biscuits, roasted grapefruit, and pomegranate

Down in the galley, Annie has been up since 4:30 a.m. preparing for the day ahead which includes cajoling a temperamental Lucy, her vintage wood-burning stove.  Her assistant Mark (“Chives”) Godfrey, is busy prepping ingredients for today’s meals. Annie will cook for 26 people in an area the size of a walk-in closet.

“Morning,” I say, taking a seat next to Susan who’s already slicing fruit into a bowl. 

“What can I do?”

Guests and crew working the windlass on the J & E Riggin - Windjammer cruise in Maine
Guests and crew hauling anchor with the windlass

Though we’re not required, passengers are invited to help with the day-to-day tasks of running the ship, and throughout the trip we all do. I fancy mornings in the galley. It’s snug and homey and everyone is in a good mood, albeit groggy and a little disheveled.

We chat while we chop and peel, drifting from subject to subject—our lives, the latest movies, books—whatever comes to mind. I joke we’re the culinary equivalent of an old knitting circle.

Jon Finger, Elle Finger, Annie Mahle of the J & E Riggin -Windjammer Cruise in Maine
Jon, Ella, and Annie on McGlathery Island after our lobster bake

Annie shows me how to properly whip cream–from side to side not in a circle like scrambled eggs–then deftly rotates her pots and pans and baking sheets on Lucy with the speed and precision of a Las Vegas croupier.

The Riggin has a reputation for serving the best cuisine of any windjammer in Maine. And we’re not talking gourmet hot dogs. Think fresh fettuccine with lemon-spinach Alfredo sauce, Mediterranean-style lamb chops, succulent pulled-beef sandwiches, paprika-rubbed Cornish game hen, or poached salmon with nectarine and pepper salsa.

She calls her cooking swanky comfort food. Everything is from scratch and often a twist on her own recipes. “I love to riff,” she says, which is fortunate considering cooking on a ship with limited space, a galley that tilts, and an oven that overheats when the wind blows, requires skilled improvisation.

A sailboat in Buck's Harbor - Windjammer cruise in Maine-593220180704
A view of Buck’s Harbor from the Riggin

When meals are ready, Annie rings a brass bell and everyone yells, “We love you, Annie!”  I have no idea when, why, or how this started and it really doesn’t matter. By the end of the trip, we all have our reasons. 

Dining is family style on the deck. There are no tables or assigned seats, we grab a spot and cop a squat. Day after day, I tell myself not to go for seconds but I can’t stop. Eventually, I give in to my shameful lack of discipline and roll with it. I’ll work out when I get home-right? 

On most mornings after breakfast, we get underway. Led by the crew, four people (two on each side) work the giant metal arms of a seesaw-looking contraption called a windlass. When pumped, the chain attached to the 500-pound iron anchor wraps around a winch, pulling it out of the water. On modern vessels, the windlass is hydraulic, on a historic schooner, it’s powered by guests and crew. 

Oysters on the half-shell, fresh baked bread and various olive oils to dip - Windjammer cruise in Maine-520220180702
In honor of the Riggin being a former oystercatcher, hors-d’oeuvres of oysters on the half shell, fresh sliced baguette and virgin oil tasting, grated beet and horseradish relish, mignonette, butter, plus pecan and sesame dukkha

Meanwhile, two single-file lines form on each side of the boat. The job is to pull on a 3-inch thick rope attached to both sides of the sails. The effort results in a mean tug-of-war with the swelling canvas as it’s yanked up the mast. Since the Riggin is a two-masted schooner (some ships have more), we get to do this twice.  

At first, I have no clue what I am doing but between the relics and the crew, newbies like myself are made to feel right and home and before long we are a well-oiled machine. Go team Riggin!

Swans Island Lighthouse - Windjammer cruise in Maine-572220180703

In keeping with its heritage, the ship lacks a motor and our journey is at the wind’s discretion. Cap knows where we’re headed of course, but for us, it’s an entertaining mystery.

Along the way, we pass fishing villages, storybook lighthouses, and dozens of small islands with epic rocky shores bordered by expansive pine forests. The scenery is ever-changing, the only constant is the hundreds of lobster buoys scattered across the waves as if God sprinkled foot-long confetti on the water. 

During the six days, there are only a couple of scheduled activities the rest we play by ear. “Our ethos is that you don’t have to do anything on vacation unless you want to,” Annie tells me. A philosophy we embrace to the fullest. 

When we’re not eating some nap, play board games, knit, read or help with the boat. A few go swimming (too cold for me). I take pictures and hang out with the other guests. With little cell service and no wi-fi—translation: no phones glued to our palms—conversations are refreshingly present, and I’m relieved to put the internet on the shelf for a few days. 

The J & E Riggin from McGlatherly Island - Windjammer cuise in Maine-620620180704
The J & E Riggin from McGlatherly Island where we had our traditional Maine lobster bake

Twice on the trip, we take to the shore to explore Buck’s Harbor then Stonington, two small towns we anchored near. Cap ferries us over in shifts in the yawl—the small motorboat schooners carry to push the ship should the wind die.

In Buck’s Harbor, we stroll 10-minutes down a windy, tree-lined road into nearby Brooksville (pop. 916) to check out the Tuesday market. In a small parking lot, we find local vendors selling an eclectic mix of products from goat’s milk soaps and salt-air caramels to hunting knives and scallop shells decorated with hand-painted nautical scenes.

In Stonington, we stay just long enough for most of us to wander through the Marlinespike Chandlery, a Marlinespike ropework shop containing a fascinating array of nautical artifacts and antiques.

Guests and Crew stow the mainsail -- Windjammer cruise in Maine-720020180706

Back on the Fourth of July…

The Queen concert put to bed (though honestly, it takes me a while to stop giggling), Jon grabs his guitar and Annie and Ella take center stage on the companionway.  I’d heard about this, it’s a Riggin tradition for the family and crew to entertain guests with a night of music and song.

I’d heard Annie and Bella sing once before in the galley. Louis (“Hop to”) Koll, one of the crew, was drying pots while the ladies were making pasta. Out of the blue, he breaks into song— a folk tune called “Ambletown (Home Dearie Home).” Not missing a beat, Annie and Ella harmonized.

I remember thinking how unusual and wonderful it was. Unusual because Louie is a young 20-something guy, and the men I know his age would never start singing out of the blue, alone, especially with strangers around. And wonderful that he’s found work that’s so welcoming and safe that to do so would be second nature.

But I digress.

Jon Finger, Ella Finger, Annie Mahle sing above the J & E Riggin-- Windjammer cruise in Maine-636620180704

Shoulder to shoulder with Annie’s hand lovingly on Ella’s knee, Annie begins to sing “Southern Cross” by Crosby Stills and Nash channeling an ever so slight Stevie Nicks in the process. The rest of us join in for the chorus but mainly we relax and listen.

Bella follows with a bluesy, unplugged rendition of Humble Pie’s “Don’t Need No Doctor.” Reflexively, our heads bob as if we’re in a 1960’s coffeehouse. Jon solos with “What A Lucky Man He Was” by Emerson, Lake, and Palmer with a little chorus help from the ladies.

As the music rises and falls, I think about childhood campfires, school plays, a trip with friends to Sicily, a birthday in Cannes, moments in life where I really felt connected to those around me, and I know the memory of this day will find a home with the others. I understand why the relics return.

In the distance, fireworks shoot into the sky. We gather at the stern for the show, watching, together, as the night bursts with shimmering color.

I was a guest of the J & E Riggin, however, the writing and sentiment are my own. 

How You Can Enjoy A Windjammer Cruise on the J & E Riggin

Annie and Jon offer three, four, six and one 7-day windjammer cruises in Maine during the 2019 season which spans from the end of May through September.

Every departure has a loose theme. I went on the “Schooner Race” trip which includes the 4th of July holiday. I didn’t get into the race aspect of this trip because it only happens once during the summer and I wanted to share the experiences that are the most universal.

Trip themes include Maine food, cooking with Annie (I bet this would be awesome if you’re into cooking), knitting, lighthouses & lobster, among others.

Windjammer cruise prices range from $772 – $1500 per person.

Note: Sixty-five percent of Riggin passengers return meaning their departures fill up fast. If the trip sounds good to you, I suggest making reservations now. 

Things You Should Know

How to get there: The Knox County Regional Airport in Rockland (RKD) is about a 5-minute drive from the dock on Captain Spear Drive where the Riggin is docked. Uber and Lyft are both available but may not be as quick as a bigger city. You can also call Schooner Bay Taxi at 207 594 5000 but I recommend you call ahead and arrange for a pickup.

( I took a Greyhound bus from NYC’s Penn Station to Rockland with a change in vehicle in Portland. I left around 7:30 am and arrived in Rockland roughly 5:00 pm. It was cheaper than flying and very comfortable. Amenities include wi-fi and movies.)

Guests board the ship between 6 pm – 7 pm in the evening before the scheduled departure to get settled and learn about the boat (orientation, safety, etc). The first meal served is breakfast the following morning. There are a variety of restaurants on Main Street near the marina.

If you want to explore Rockland a bit before or after your sail, try the Granite Inn B & B near the marina. It’s super cute and reservations include a hearty breakfast.

The J & E Riggin - Windjammer cruise in Maine-731720180707
The J & E Riggin

About the J & E Riggin

The trip is truly memorable but it’s not for everyone. If you need luxury, 24/7 internet or activities scheduled up the wazoo to have fun, this isn’t for you.

Cabins are snug. If you’re tall, best to give Annie and Jon the heads up so they can keep that in mind when assigning cabins. Be aware that you have to go up and down steep steps (almost ladder steep) from your cabin to the deck. If you have mobility issues please keep this in mind. There’s a small sink for brushing your teeth and a pitcher to freshen up. (Warm water for the pitcher is available in the galley.) I found my bunk to be very comfy.

There are two shared bathrooms (one doubles as a shower) on deck.

Electricity is run by a generator.  If you want to charge batteries or a phone, let Jon know and he can plug it into a shared electrical strip. The internet is sketchy at best. Some people had better connections than I but overall don’t count on it.


Annie and Jon run a sustainable business. You won’t find any unnecessary plastic on board (each guest chooses a ceramic mug to use throughout the trip) and everything that can be recycled, is. Any office paper, magazines, go back into the compost or the garden. All the food waste from the Riggin is transferred to Annie’s home garden and composted.

Pumpkin and black pepper cupcakes with buttercream frosting - Windjammer cruise in Maine-560320180703
Pumpkin and black pepper cupcakes with buttercream frosting

Drinks and snacks

The Riggin supplies water and lemonade to drink. Anything else you may crave you should bring yourself. The same thing with snacks, though Annie keeps you so well fed it’s kind of overkill.

I bought Diet Coke at the local Rite Aid (Main Street and Park) about 4 blocks from the marina. You’ll have plenty of time to stop by after your orientation on the boat the night before departure.

There’s a great wine store called Wine Seller across from Captain Spear Drive where the boat docks. I purchased a few bottles of Sauvignon Blanc for the trip. FYI.. It closes at 6 pm on Weekdays and Saturdays, and 5 pm on Sunday.

What to pack on a windjammer cruise in Maine:

Approach packing as if it were early fall: Warm during the day but times when it can be chilly. You’ll want layers.  It can get cold on the boat if the wind is blowing. I was there in July and I wore t-shirts as well as a jacket and a warm hat. The weather changes by the hour sometimes.  Rubber-soled shoes like sneakers are the best for getting around. Make sure to bring plenty of sunscreen, a hat for protection, and bug repellent. I also recommend a rain jacket and pants. Binoculars. Camera. Flashlight. On the ship you can hear people talking, snoring, you name it, so bring earplugs if you’re a light sleeper.

Note: Since the cabins are tiny I suggest using luggage without wheels so you can slip it under your bunk. 

Our route

Rockland --> Buck’s Harbor --> Burnt Cove Harber (Swans Island) -->McGlathery Island (Lobster Bake)--> Stonington (Deer Isle) --> Gilkey’s Harbor (Islesboro Island) --> Rockland

(Note: Every trip is different depending on the prevailing winds)

For regular updates sign up for The Insatiable Traveler’s newsletter

For Pinterest

12 thoughts on “Finding Comfort and Camaraderie on a Maine Windjammer Cruise

  1. DON PARCHMENT says:

    The cruises to the various destinations as depicted by your photography seems an exciting and worthwhile adventure.

  2. Ed Dentch says:

    A truly wonderful article ! Your descriptive powers are enticing. Anyone not considering this trip has no adventure in their sole !

    • Susan Portnoy says:

      Thank you so much, Ed.. I really appreciate your kind words. Welcome to the blog. I hope to see you again. Would you be interested in my adding you to my newsletter?

  3. K.M. Sutton says:

    This sounds amazing! Every year around my birthday I take a schooner ride, usually out of Portland, Maine and I absolutely love it. Something so incredible about sailing on a boat hundreds of years old, just letting the wind take you wherever. I will have to look into this! Thank for sharing! <3

  4. Heide says:

    What a wonderful post, Susan … I feel as if I’d been right there with you (and yet still desperately want to experience this for myself). Annie and Jon sound absolutely wonderful, too — talk about the perfect hosts!

I would love to hear from you! What did you think of the post?