The Rusticator’s Guide to Maine Windjammer Cruises: Sailing On the J. & E. Riggin

Maine Windjammer cruises are famous in the region of Penobscot Bay, Maine, and sailing on one is a lot like stepping back in time... a perfect way to experience slow traveling at its best.

We’d been camping near Rockland and Camden, Maine for years but didn’t know much about the Maine Windjammer ships other than watching them sail majestically past Owls Head or Rockland Breakwater Lighthouse and dreaming of one day being onboard.

So when we were invited to go on a 4-day Lighthouses and Lobsters cruise with Captains Jon Finger and Annie Mahle onboard their schooner, the J. & E. Riggin, we jumped at the chance.

Update: Since this article was published the J. & E. Riggin in 2020 came under new ownership. We haven’t met the new owners yet but they are long-time Riggin Relics, and we’re looking forward to our next sailing adventure with them!

Foresails on the J. & E. Riggin

Foresails on the J. & E. Riggin

As we pulled out of Rockland Harbor, we thanked the weather gods for blessing us with blue skies in early June and a clear forecast for the next few days.

The sails went up and the crew scurried about tightening lines and stowing ropes, while the rest of us 22 passengers watched in awe, stepping aside as they worked around us, and began to settle in to the gentle bobbing rhythm and the sound of the sea swishing against the hull.

It’s an incredible feeling to be on the deck of a massive wooden schooner as it comes to life and begins to set sail on the open water.

We’re the modern day Rusticators — what Mainers called out-of-state summer vacationers who flocked to coastal Maine in the late 1800’s and who artist Winslow Homer famously tried to scare away from his coastal home with a sign that read “Snakes! Snakes!…and Mice!”

We were setting sail on a windjammer cruise for the rocky islands and hidden coves along coastal Maine and it didn’t take long for us to realize just how rustic it might be. Our cell phones showed no signs of life. What on earth would we do for days on end with no reception?

And what is that deafening sound? Other than the gentle wind, there was simply… silence. As the days wore on, we sailed near an occasional wifi hot spot or borrowed bits of solar power from our fellow passengers, but soon realized this was exactly the point of the cruise.

To unplug, reenergize ourselves, travel slow, and connect with new friends over tasty food, lively conversation, spirited music, and a good book or bottle of wine.

Hark, now hear the sailor’s cry, Smell the sea and feel the sky. Let your soul and spirit fly into the mystic.
— Van Morrison, Into the Mystic

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What Are Maine Windjammer Cruises?

The term ‘windjammer’ refers to a large schooner-type ship propelled by sails, and cruises where the destinations are influenced by the winds and tides. There are windjammer cruises around the world including the Bahamas and Caribbean, but Maine has nine such ships based in Rockland and Camden which run schooner cruises on Penobscot Bay.

Some of these schooners were at one time true merchant ships engaged in fishing and oystering along the United States’ eastern seaboard. Several are historic working vessels built in the late 1800s and early 1900s that have been outfitted to be the passenger cruising vessels that you now see.

One of the newest in the fleet — the Angelique — was recently built in 1980. The schooners vary a bit in size, accommodations, and the number of guests that can be hosted, but all of these Maine cruises invite participation in helping to crew the ship to whatever extent a guest feels comfortable.

But why Maine? The Pine Tree State’s distinguished maritime history was once dominated by these merchant sailing vessels.

Today they allow passengers to see the beauty of Maine’s rugged coastline, its many islands and the historic lighthouses that dot Penobscot Bay while experiencing living aboard a windjammer schooner if only for a few days.

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The J & E Riggin Schooner

We sailed aboard the J. & E. Riggin Schooner named for Jacob and Edward, the sons of the original owner, Charles Riggin. Originally used for dredging oysters on the Delaware Bay, she is considered a fast light air schooner.

But she didn’t always look this pretty. The dredged oysters were once dumped on the midship deck area where there are now cabins.

From our first steps on board, the boat looked spotlessly clean and tidy with all ropes coiled and the painted surfaces gleaming. Despite the historic atmosphere and lack of electricity, the ship is equipped with modern navigation equipment and outfitted to comfortably accommodate 24 guests below deck.

Mother, mother ocean, I have heard you call. Wanted to sail upon your waters since I was three feet tall.
You’ve seen it all, you’ve seen it all
— Jimmy Buffett, a Pirate Looks at Forty

Our 4-Day Cruise Itinerary and Anchorages

After checking in on the boat Thursday evening, we were introduced to Captains Jon and Annie and the crew Chlöe, Louie, and Liza. Captain Jon gave us all a thorough briefing on safety instructions and what to expect during our trip, and then we headed into town for dinner and to pick up a few items like snacks and wine.

Since windjammer cruises are dependent on the weather, wind, and tides to determine their itinerary, our 4-day cruise may differ slightly from yours, but here is an overview of where we sailed and anchored.

Day 1: Hell’s Half Acre Island

Ship’s Log:


Fresh brewed coffee and hot water for tea were waiting for us along with fresh baked muffins still warm from the oven of the galley’s cast iron stove. After a good night’s sleep onboard and our first Chef Annie breakfast, we departed Rockland Harbor at 10:30 am with the ship’s diesel powered tender first pulling then pushing the boat.

Once clear of the harbor and the Rockland Breakwater and Lighthouse, sails were set and we were underway. There wasn’t much wind on this day but enough to get us across Penobscot Bay to North Haven Island.

Along the way we passed Owls Head Lighthouse, countless brightly colored lobster pot buoys, cormorants, harbor seals, and osprey nests on small rock islands.

We passed the Fox Channel Islands, North Haven and Vinalhaven, and made our way through the Fox Island Thorofare passing Browns Head Lighthouse at the start of the channel and the Goose Rock Lighthouse as we made our way onto more open water.

Once across the East Penobscot Bay we passed the town of Stonington at the southern tip of Deer Isle, and Crotch Island where granite is still being cut.

Because of its Italian ancestry, there is a popular Opera House in Stonington where renowned opera stars still perform. Our first lunch was served underway.


Captain Jon dropped anchor sheltered by Hell’s Half Acre Island. After some light hors d’oeuvres, we enjoyed our first dinner onboard and it was really incredible.

The evening water was calm but still only 49° and one intrepid passenger dove in for a quick dip while the rest of us enjoyed the warmth of the bright sun on deck. But as the sun set, the temperature quickly dropped with it and the chilly breeze picked up.

Time to add more layers. The clear night was beautiful with so many stars overhead. Some of us had a little wine.

After a day in the sun and wind, and with our bellies now full, most everyone went off to their cabins by 9:30pm. It’s amazing how easy it is to fall asleep with the gentle motion of the boat at anchor.

Day 2: Babson Island and A Lobster Bake

Ship’s Log:

We were struck by how early it gets light in Maine compared to our home in Florida. Out on deck for a crisp walk to the restroom (head) at 5:00am and it was already bright and sunny.

Sometime during the night the boat had swung on anchor and was now facing in the opposite direction.

We heard our shipmates chatting on deck at around 7:00am so up we went for coffee and Annie’s morning surprise, cranberry chocolate scones. We could have stopped there but breakfast appeared right on time at 8:00am.

Our sail to Brooklin was as scenic as coastal Maine gets. Small rocky islands adorned with pine trees, many with cormorants, gulls, and seals taking a nap in the sun. We had good wind, a gentle sea and Captain Jon took us in close for a view of the Bass Harbor Lighthouse, one of the most photographed lighthouses in Maine.

Bass Harbor is the gateway to Acadia National Park, camping on Mount Desert Island, the famous Cadillac Mountain, and the tourist town of Bar Harbor. In this setting on this day in the sun the lighthouse was really beautiful. We reversed course and the Captain put us at anchor at 4:30pm off the uninhabited Babson Island.

Tonight was to be a night that Maine dreams are made of!


We’d heard some repeat passengers talk about the Down East lobster bake on the beach, and as we gazed out at secluded Babson Island, we couldn’t believe we’d have the entire island for our feast! It was a gorgeous place to explore and relax over dinner.

Captain Jon delivered the crew members to the island in the ship’s tender with everything they needed to start the wood fire and get set up. The rest of us were ferried six at a time bringing along our beverages of choice like wine, water, and of course, rum.

We were on the last trip out to the island, and when we arrived the fire was going and the lobsters and ears of corn were in a metal washtub with a bit of water covered by a thick blanket of seaweed.

While things were cooking we took time to hike part of the nature trail that winds around the small island. Pine trees covered with lichen and moss lined the path and bits of clam and crab shells from feeding seagulls littered the ground. In the middle of the island was an open field strewn with granite boulders and bright with knee high baby green ferns.

Annie told us how her girls loved running through this field when they were little and not even as tall as the ferns — we giggled just thinking about that. It was so peaceful here aside from the ever present mosquitoes who seemed as hungry as we were.

Back on the beach, it was time to welcome the guests of honor, those now bright orange lobsters who gave their all so we could feast. A steaming bed of seaweed was laid first, then over went the tub. Lobsters and corn were stacked for optimal photo beautiousness!

Everyone got a lobster, an ear of corn, baked potato, and a small cup of melted butter to start — and some salad greens if you wanted. But more than a few hungry lobster lovers went back for seconds, thirds, and more.

If you’ve never had corn on the cob steamed with seaweed and lobsters, you’re in for a real treat. For folks who didn’t care for lobster or who don’t eat shellfish, Chef Annie had prepared a delicious sausage paella, which was out of this world!

In keeping with the Riggin’s eco-friendly philosophy, when the bake was over and it was time to go back to the boat, we left only footprints.

Not even the remains of our fire could be seen since the fire was built on a metal fire pan and the ashes and unburned wood hauled back to the boat. As for the lobster shells, they were given a quiet burial at sea.

As if tonight’s lobster bake wasn’t fabulous enough, back on the boat the fiery sunset that lit up the sky went on forever, and the water was as calm as glass. Everyone seemed to simply bask in the glow of our amazing day, very aware of how fortunate we were to have had such great weather.

Red sky in morning, sailors take warning, Red sky at night, sailors delight!
A beautiful morning on board the Maine Windjammer Schooner J. & E. Riggin at anchor

A beautiful morning on board the Maine Windjammer Schooner J. & E. Riggin at anchor

Day 3: Brooklin, North Haven Island, and Pulpit Harbor

Waking up on a big sailboat on a beautiful morning is something special. The calm water remained this morning and we heard the sounds of loons and gulls. A seal’s head broke the calm surface, and the smell of the sea was thick in the air.

Some of our shipmates decided to go ashore to visit the small town of Brooklin, famous for its wooden boat building. On their return, sails were set and we were off.

The wind had picked up and things were a bit choppy, windy and cold on deck. Some folks opted for their cabins, others went down to the galley to stay warm, help out and read.

Captain Jon got us across the bay to our next anchorage at Pulpit Harbor at North Haven Island without too much spray coming over the bow. At the entrance to the protected harbor was Pulpit Rock, a small but tall chunk of rock sticking up out of the water.

At first you might think this is just another seastack that are so common along these shores, but this one is unique. Pulpit Rock is famous for the ginormous osprey nest that’s been documented in this spot for nearly 200 years, and ospreys are still nesting there.

This was the first time we anchored in a place with other boats around us, mostly private power and sailboats along with a few working lobster boats as well.

This was our last night onboard and as is customary on the Riggin, it ends with fun and songs. Captain Jon played his guitar while he, Annie, Chlöe, and sometimes Louie, sang sailing songs and sea shanties (sung while working on the old sailing ships to keep a steady rhythm, like when raising the sails).

This was such a fun night and a great way to bring our sailing adventure to a close.

Day 4: Homeward Bound to Rockland!

Because of the previous day’s wind and sea conditions, we got an earlier start to the day. There was far more activity on deck around 6:30am instead of the usual quiet chatter.

Folks were busy lowering the awning, and the crew was getting ready to raise the anchor and hoist the sails. With a hand-over-hand and a 2-6-heave, sails were hoisted and we were underway by 8:00am.

Once on open water it was much different than the day before. The sun was bright but the wind was cold as we headed for the Riggin’s home port of Rockland.

In 4 days of sailing, we’d criss-crossed the islands in Penobscot Bay and had ourselves quite an adventure, though it now seemed way too short as we entered Rockland Harbor.

Tying up to the dock we felt relaxed and exhilarated, but a little sad at the same time that it was ending so quickly.

Meals and Food

Sailing on the J. & E. Riggin is made even more special with Chef Annie Mahle’s cooking. It’s a well-known distinction that sets the Riggin apart from other Maine windjammer cruises. In fact, her cooking is so well-known, it comes as no surprise that she’s also a celebrated cookbook author as well!

There was so much good food on this cruise, and to see how she prepares it all in the tiny 6 x 6’ galley space is even more amazing.

Our days began with fresh coffee or assorted hot teas, followed by breakfast appeteasers like freshly baked danish, cinnamon muffins, and cranberry chocolate scones. Lest you think that’s all there is to start your day, you might be inclined to overindulge, but then Annie rings the bell 3 times to signal that the full meal is onboard!

One thing we really loved was her introduction to the food. After the bell is rung, she describes what’s on the menu, where it came from, and how it was prepared.

Some of the food Annie serves is grown in her own garden and she also belongs to a CSA (community-supported agriculture) network of 30-40 growers and producers in the Rockland area who produce food organically and sustainably. How awesome is that!

While not everything served onboard is completely organic, her dishes were all fresh, creative, and locally-sourced, not to mention beautifully presented! Entrees always included freshly prepared sauces and were surrounded by small garnishes of fresh flowers or herbs. Trust us, you won’t go hungry.

And while you may think you need to stock up on snacks in your cabin, we never felt the urge to eat a single one.

Here are examples of some of her tempting menu items:


Buttermilk pancakes, Annie’s homemade granola, fresh fruits, breakfast frittatas, bacon, and oatmeal. Being oatmeal lovers, we found Annie’s version unique and yummy.

First, she pan sautés the dry oats in a little butter before cooking them with water, giving them a nuttier flavor. Top the oatmeal with hot apples and raisins, a drizzle of almond milk and it was an incredible breakfast.


Our first lunch onboard was a favorite: Duck egg carbonara, fettuccini linkorn, roasted feta cheese, eggplant caponata, fresh basil pesto, baby arugula salad, and a relish tray of roasted peppers and warm olives.

One day Annie served chicken and veggie pot pie with a flakey buttery crust, a white bean and roasted zucchini salad, pickled red onions, a baby kale and baby arugula salad, and bite-size cheddar cheese.

My favorite lunch was Vietnamese vermicelli noodles and savory meatballs in an Asian-flavored broth with bowls of fixins to add on top, like tofu, julienned cukes, ground peanuts, and fresh chopped herbs.


Fresh salmon, black rice and quinoa, mango salsa, fresh baked and still warm oatmeal cardamom bread, with a baby kale salad with fried garlic cloves.

For our last night onboard we had Prime rib roast, oyster mushrooms and lobster pieces, seared romaine, and fig and orange challah bread.


Shortcakes with a rhubarb cherry sauce and fresh whipped cream. Blueberry lemon cake that was absolutely yummy. Lemon white chocolate cheese cake.

Spiced ginger whoopee pies with marshmallow fluff in the middle (and a small bowl of rum to dip the pie if you’re so inclined)!

What’s Not Included

Alcoholic beverages are not provided, but you are welcome to bring your own onboard. There are plenty of shops in Rockland to buy beer, wine, and anything else you might want, and a cooler onboard to keep your beverages cold.

Tempted by Chef Annie’s Cooking? Pick up her cookbooks on Amazon.

Cabins and Accommodations

The cabins onboard are very small, but comfortable. There is a small basin with cold running water and because we were in Cabin 1 in the bow, a small foot pump to drain the water. Each of our two berths were about the size of a sleeping bag.

There are nine cabins with two single berths, two cabins with three single berths, and two cabins with double berths. If you’re in the top bunk, watch your head and don’t sit up too quickly.

All it takes is one good whack and you’ll move more slowly! OUCH!!

As for floor space, there really isn’t any, just room to stand up and turn around.

Our tiny cabin wasn’t a surprise to us, but it reminded us why they suggest you bring a soft duffel and pack light. We stowed our small bags under the bottom bunk after moving what clothing we might need to two small shelves at the foot of our bunks.

The folks in the cabin across from us resorted to leaving their door open most of the time. I guess it gave the illusion of more room.

But hey, you’re on an almost 100-year old working schooner — in its heyday this would have been considered luxurious. As for other cabins, it’s bad manners to peek into someone else’s cabin, but we heard no complaints.

Everyone seemed to have their expectations in line and were enjoying their accommodations as part of the experience. It doesn’t take long to get used to your quarters and it’s truly part of the fun.

Oh, the canvas can do miracles, just you wait and see. Believe me.
— Christopher Cross, Sailing

What Is It Like Sailing on a Maine Windjammer Cruise?

Life Onboard

You’ll spend about six hours each day under sail meandering through the islands and bays of mid-coast Maine, and every afternoon the captain will drop anchor in a safe, snug harbor off a quiet fishing village or an uninhabited island.

There are plenty of places to sit and chat throughout the day including the galley (kitchen) where there are tables with lots of seating along with a small library.

The galley is a popular place to be if you want to chat over food and see what’s coming out of the cast iron stove next. Just know that if Annie is in the galley prepping for the next meal, you might just become a volunteer.

Put down your book and pick up a paring knife to help out and maybe learn a song or two.

On deck, there is plenty of room to move around and quiet places to sit. Even at mealtime when underway, finding a comfortable spot was never a problem. Some folks brought along their own padded stadium seats made for sitting on bleachers.

They seemed comfortable enough but there is a downside. They’re lightweight and on a sailboat, so if it gets windy enough there’s a chance it could go overboard.

It only takes a day to lose track of time. You rise and sleep with the sun and your rhythm joins with the boat and the wind. Sun up, breakfast, weigh anchor, set sails, lunch, drop anchor, furl sails, dinner, sun down, chat, get comfy in your bunk and sleep. Nothing is hurried.

Relaxing becomes the norm and the only one who stays aware of the time is the captain. True, some days are windier or colder than others, but as Captain Jon says, “That’s sailing”. Stay mindful of that and the experience will take over, not whether it’s raining or chilly.

Helping to Crew

The crew will ask if you’d like to help out and will indicate when help is needed. This was a lot of fun and truly makes you feel part of things, a participant and not just a spectator. Just about everyone took a turn at helping to raise and lower the sails with lots of smiles and high fives at our success.

Raising the anchor is something else altogether. It takes a strong back and legs and can leave you huffing and puffing, but was still fun for those who jumped in.

When you feel you’d like to try your hand at something, just ask a crew member. They’ll either give you direction, or if the time isn’t appropriate they’ll at least explain what they’re doing. The crew was always friendly, courteous, and incredibly adept at what they do.

Ready on the peak! Ready on the throat!

What to Pack

Packing for traveling can always be a challenge, but packing for a Maine windjammer cruise was new to us, and even more daunting! The idea of being onboard for several days can leave you confused and wondering what to bring.

Will it be hot or cold? Will it rain? And what about your feet? Should we pack everything just in case?

Maine is a place where the weather can change in a minute, and when it comes to living on a boat for several days, it usually does! Unless you’re a frequent camper or a boater, it’s easy to overpack for a windjammer cruise no matter what time of year you’re going.

Our best tip? BRING LAYERS!! And rain gear, just in case! Then check out our packing list for a complete list of what to bring.

Head to toe in wind and light rain gear

Head to toe in wind and light rain gear

Fortunately, we can help to keep you from overdoing it and taking only what you’ll need for whatever Mother Nature serves up. Because you’re going to Maine and you’ll be on open water, our guidance on what to pack is this — it’s one thing to be cold, it’s quite another to be wet and cold.

Who Will Love a Maine Windjammer Cruise?

Maine windjammer cruises onboard the J. & E. Riggin are rustic adventures. If you’re thinking of taking a windjammer cruise, consider these first:

  • The cabins are tight but cozy with plenty of warm wool blankets.

  • There are no private bathrooms on board. Everyone onboard the J. & E. Riggin shares two heads (restrooms) with pump toilets and limited use of toilet paper!

  • Showers or baths are best enjoyed in the ocean as fresh water onboard is a valuable commodity. An onboard shower is available twice a day, before breakfast and after anchoring in the evening. Annie will also give you a pitcher of warm water for your cabin basin.

  • You will be in close quarters with your fellow passengers, including (above) the sharing of restroom facilities.

Nighttime on board

Nighttime on board

Our 20 fellow shipmates for the trip were well-traveled and adventurous folks in their 40s, 50s, 60s, 70s, and 80s. Everyone was so friendly and some had years of cruising aboard the Riggin with lots of interesting stories to share.

If you do at least three cruises, you become a member of the esteemed “Riggin Relics”, and burgee flags will be hoisted up the mast to let all know you’re on board! We had such a great time getting to know them and chat about their travels around the world.

If you enjoy camping and/or glamping adventures like sleeping outdoors, moving about in small spaces, and simple pleasures like conversation, reading, traveling sustainably, and watching the landscape pass you by, this might be the perfect experience for you.

We’ve been avid tent campers for years and now that we’re older, we’re always up for a good glamping experience.

While this sailing vacation isn’t as glam as some glamping experiences we’ve had — like in Chile and Slovenia — we think the level of cuisine (including the lobster bake) and the overall comfort factor would place it solidly in that category.

If you’re Travlinmad too and share our love of slow travel and adventure, we think you’ll love sailing on the J. & E. Riggin as much as we did!

  • Perfect for: Slow travelers, outdoor lovers, adventure and food travelers, campers/glampers, and adventurous families

  • Not-So-Perfect for: 5-star luxury travelers, travelers prone to motion sickness, cell phone addicts, and germaphobes

Windjammer Tips for Newbies


If you’re prone to motion sickness, bring Dramamine. Hanging out below when the boat is underway isn’t such a good idea. Stay up on deck where you can see the horizon and get fresh air.

Keep food in your stomach until you’re used to the motion of the seas — Chef Annie always has crackers and other nibbles when you need them!

Keep Dry

Pack a Dry Bag — The boat can be a damp environment and can quickly become a very wet environment if it rains. Pack a dry bag or dry sack like the ones used by campers and kayakers.

Windjammer’s Philosophy

Take only photos, leave only footprints!

Pack Light

It’s tough knowing what to pack for your windjammer cruise. Trust us, you aren’t going to need a lot of clothing changes, just lots of layers!

Where to Stay in Rockland, Maine

If you haven’t yet been to mid-coast Maine, it’s so charming any time of year and the town of Rockland is especially so. There are a lot of unique things to do in Rockland for foodies, art lovers, and eco and adventure travelers with a good dose of small town charm mixed with good restaurants and world-class museums.

As you start planning your Maine windjammer cruise on the J. & E. Riggin, you may find you’ll need a place to stay on the way in, and on the way out. We recommend staying at a hotel in Rockland, Maine both before and after your first night on the Riggin.

250 Main Hotel

The 250 Main Hotel is in the heart of just about everything to see in Rockland and walking distance to the Schooner J. & E. Riggin. This beautiful modern boutique hotel is designed with an industrial decor reminiscent of boat building, and makes use of repurposed materials.

Its 26 rooms are conveniently located on Main Street overlooking the water and Rockland Harbor. While the rooms are modern, they’re also well-designed and so comfortable.

We loved the excellent attention to detail like the luxurious Malin & Goetz toiletries, the bedside tablet, the overhead dim-able lighting, and the huge walk-in shower with that rainfall shower head. After 4 days on a boat, a hot shower never felt so good!

Guests can enjoy a complimentary glass of wine on the rooftop terrace — where the view is worth the stay alone! Restaurants are close by, and coffee and tea are available throughout the day as is fresh or sparkling water from the dispenser in the lobby using a refillable glass bottle.

We loved our brief stay at this hotel and highly recommend it for your stay in Rockland.

250 Main Street, Rockland, Maine

Getting To Rockland, Maine

Flying into Mid Coast Maine

The closest airport to Rockland, Maine is Portland, Maine (PWM), which is approximately 1.5 - 2 hours away depending on traffic.

Driving To Rockland, Maine

There are several parking spaces at Windjammer Wharf, home of the J. & E. Riggin. You can leave your car here if you book far enough in advance.

Check the J. &. E. Riggin website for more details.

Learn More

Schooner J. & E. Riggin(boat) Windjammer Wharf, 3 Captain Spear Drive, Rockland, Maine 04841 | Facebook | Instagram | Chef Annie Mahle’s Blog, At Home At Sea

Many thanks to Captains Jon and Annie and Crew of the Schooner J. & E. Riggin and 250 Main Hotel for hosting us on this trip. As always, all opinions, stories, and photos, are ours alone based on our firsthand experience.