When I signed up for a Maine schooner tour, I imagined Maine’s rugged coastline, billowing sails, and the sound of waves against the hull – but what I discovered was so much more.
For three nights, I traded the rush of everyday life for the steady rhythm of the ocean aboard a historic windjammer in Maine. From meals served on the polished wooden deck, to cozy cabins tucked below, every detail carried a sense of tradition and history.
I’m thrilled to share the entire experience with you, including what daily life was really like on board, the food, the cabins, and the iconic views that Maine’s coastline is known for.
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My tour was hosted by the Maine Windjammer Association.
Honesty and authenticity are my highest priorities, so all opinions are always my own.
Why Book A Maine Windjammer Tour?
In short, it’s a way to step into living history that represents New England’s maritime trade, while also allowing yourself a real escape from the outside world. It’s truly an authentic New England experience like no other.
The schooners in the Maine Windjammer Association aren’t replicas—they’re the real thing, many of which once hauled cargo, or fished the very same waters you’ll explore during your excursion. Each boat has incredible stories to tell, and a fascinating history to discover.
Today, five of the vessels are recognized as National Historic Landmarks, allowing you the rare chance to sail aboard working pieces of New England history. What makes the experience truly special is how seamlessly it blends heritage with the luxury of soaking up Maine’s beauty from an entirely different perspective – while sailing the waters of Penobscot Bay.
Many people agree that Penobscot Bay offers some of the best sailing in the world because its unique mix of natural conditions, scenery, and maritime culture. What does this mean, exactly? You’re very likely to experience calm waters since you’re not out in the open ocean (you’ll always have the mainland in sight). During your tour, you’ll may pass by quaint towns, lighthouses, Maine’s famous ragged coastline, and if you’re lucky, spot seals in the water.
About The Schooner American Eagle
The Maine Windjammer Association’s fleet consists of nine beautiful vessels, but I was lucky enough to call the Schooner American Eagle home for three nights. Our host, Captain Tyler King, is actually the youngest captain in the entire fleet, and this is one of the vessels that’s been declared a National Historic Landmark.
Built in 1930 in Gloucester, MA, it’s one of the last six remaining original Gloucester fishing schooners, which made the entire experience on the boat that much more special. American Eagle is able to carry 26 passengers, with varied cabin types, which I’ll share more about below.
Maine Schooner On-Board Experience: Cabins, Bathrooms & More
Before finally stepping aboard, I was equal parts excited and anxious. I really had no idea what to expect, if I would be able to sleep, what the shower was like, how far the bathroom would be from my cabin – the list goes on.
And while it’s not exactly easy and lavish to live on a schooner for multiple nights, it was a lot better than I thought it would be. The overall experience far outweighed the little luxuries you trade in to call American Eagle home for a few nights.
First, let’s talk about the cabins. These are all located below deck, and I really can’t sugarcoat it – they’re incredibly small. However, that’s also very standard for living on a boat, as there’s only so much space. However, each cabin on American Eagle had a sink with potable hot and cold water, a mirror above the sink, towel bars, hooks to hang hats and coats, under-bed storage, lights, and a wall-mounted fan. The mattress was comfortable, and towels and bed linens are all provided.
Because of the size of the cabins, it’s very much recommended that you pack smaller duffle bugs versus one big suitcase.
It’s good to know, too, that while in my cabin, I only had room to stand between the bed and the door in front of the sink, and that was it – I had just enough room to turn around in that space. When laying down in bed, my head would hit the ceiling if I sat up. It definitely takes some getting used to.
Personally, I have trouble sleeping under the best of conditions, however, I didn’t sleep as badly as I thought I would. Noise does easily travel throughout the schooner, including down in the cabins, so bringing earplugs is a good idea if noise bothers you. Most folks I talked to about it said they were sleeping just fine. By the last night, I was sleeping as I normally would (which is fine, but not great).
Each cabin is not far from a bathroom – maybe 10 steps at most, or next door if you’re lucky. However, you’ll need to get used to calling it the head while on-board 😉
The head was also not as scary as I envisioned (I have a talent for worrying a lot about nothing, if you haven’t noticed!). They were always clean, had no strong odors, and were easy to flush with a foot petal and faucet-like knob (it sounds more complicated than it was, and no learning curve was needed).
There is one shower on-board, and keep in mind that it may not be in your cabin corridor. The shower was an adventure in and of itself! But I knew I didn’t want to go three days without using it, so it was something I had to tackle.
It’s very small, as you can imagine, and consisted of just a hand-held spray nozzle. That said, the water would get plenty hot, so that was never a concern. There was hardly any room to move around, and your things were stored in a little cabinet door along the back shower wall. It got the job done, but definitely don’t expect to take a full-on pampering shower.
While lots of food is provided, which I’ll go over in the next section, in addition to a variety of tea, coffee, and wonderful non-alcoholic drinks, you’re also welcome to bring your own beverages on-board. There’s a large communal ice box on the deck where we welcomed to store any drinks we wanted, and folks brought their own seltzers, beers, and wine – so definitely pack whatever drinks you’d like for the trip.
The Food On American Eagle
This was absolutely a highlight of the entire tour, which was due to the head Chef, Marty, and the assistant chef, Quinn. Working hard all day down in the galley with a wood-stove cooktop, they created absolutely fantastic meals for all of us.
Each morning, we woke up to a coffee and tea station on deck, along with some freshly-made baked goods to munch on before the main course was served. Typical main course breakfast offerings during the cruise were french toast, eggs, potatoes, and fresh fruit.
For lunch, we enjoyed things like chowder (which was my personal favorite), homemade biscuits, salads, and curries.
Before dinner each night, an appetizer spread was prepared with crackers, cheeses, fruits, and other light snacks. We were even treated to pickled hard boiled eggs in the spread one evening, which were so creative and delicious.
For dinners, a highlight was, of course, the traditional Maine lobster bake, which is typically included with each tour as long as the weather allows it. The crew boats everything over to an island where they begin to cook fresh lobsters, corn on the cob, and other goodies, leaving us all stuffed before heading back to the schooner for the rest of the night.
But as if that wasn’t enough, we were also treated with something sweet to end our nights, and the desserts were all just as good as the dinners.
The Day-To-Day: What To Expect & Things To Do
For a 3-night cruise, you’ll spend the first night at the dock, which I know seems a little strange, but it’s a nice way to get acquainted with not only your fellow passengers, but also your cabin and new surroundings.
Boarding typically begins around 5p (which may vary depending on the cruise and schooner), and you’ll have some time to get settled, listen to the Captain’s Call (where you’ll meet the captain and learn about the boat, go over safety things, etc.), and then you’ll be free to explore the town for a bit until you’re ready to come back and settle in for the night. I’ll have more tips and suggestions below on what to do before and after your tour.
When we first arrived, there was a wonderful fruit and cheese spread on the deck to enjoy while we all got acquainted, and were shown our cabins. However, you are on your own for dinner this night, but there are plenty of options in town nearby.
My recommendation would be to go somewhere casual this night, as you don’t know exactly when the Captain’s Call will conclude. It generally runs for about 45 minutes, but it could be longer or shorter, which makes having a dining reservation more of a challenge.
Rockland Restaurant Suggestions:
Claw’s: You could walk here if your tour departs from North End Ship Yard (which American Eagle is docked). A great casual seafood spot that would be very easy to visit after the Captain’s Call.
Ada’s Kitchen: A nice spot for Italian fare, and I’m usually able to get a table without reservations (or only have a short wait). They make their own pastas, and I also like their pizzas.
Rockland is a wonderful foodie town, and there are plenty more options. These are just my recommendations based on your circumstances for your first night.
Day 1
On your first morning, you’ll wake up in the same location, and breakfast is served around 8a.* You’ll have time to run back into town for any last-minute needs before departing around 10a.*
During your first official meal on-board, you’ll learn about forming a little food train, of sorts. Getting the food up from the galley requires teamwork, so volunteers are encouraged to form a line and pass food up from below deck. Once it’s all set-up, everyone enjoys their breakfast while taking in your last few moments at the dock.
Then, the real fun begins – it’s time to leave the dock, hoist the sails, and head out into Penobscot Bay. You still probably won’t know where you’re going at this point, but it won’t matter – you’ll quickly be surrounded by Maine’s natural coastal beauty at every angle.
If you depart from Rockland, you’ll be treated to views of Rockland Breakwater Lighthouse as you leave the harbor.
The crew welcomes more volunteers to help hoist the sails, and this is where you’ll gain a whole new appreciation for the amount of teamwork it takes to go windjamming. You’ll soon hear the captain’s voice letting the crew know when it’s time, and then the sounds of “Heave-Ho!” begin to fill the deck as the sails are raised.
The rest of your morning, you’re free to enjoy the deck space and soak up the views to your (probably still unknown!) destination. During this time, folks either read, chatted, or took photos of the scenery.
Lunch was usually served around noon each day, and on our first day out on the water, we were treated to an amazing seafood chowder with homemade biscuits and a fresh salad. We had a little chill in the air, despite it being late August, and the hot chowder was the perfect choice to serve that afternoon.
Once lunch concluded, it was back to enjoying the journey, feeling the wind on your face, smelling the fresh air, and completely forgetting about your calendar and emails.
At some point, we started to make our way to Pickering Island, just off the coast of Deer Isle, and this would be our venue for our traditional Maine lobster bake. After dropping anchor a few hours before sunset, we climbed a ladder down the side of the boat to meet the skiff, and made our way to the shore.
Stepping off the skiff onto the rocky island, we were greeted by a table with a wonderful spread of appetizers and drinks. And while we waited for the lobsters to cook, we all had free time to explore the island, or just sit back and enjoy the fact that we were the only ones there. In fact, one of the fellow passengers found a rock with fossils, which was such a cool discovery.
Once dinner was served, we all lined up to fill our plates with whole, soft-shell lobsters, corn on the cob, and hot butter. They also came around with wine to enjoy with dinner, and had extra lobsters if you wanted more. Cracking open that lobster to enjoy the fresh meat on that rocky shore as the sun began to set was truly a once-in-a-lifetime experience.
After eating, we all lined up to take the skiff back to the boat during sunset, and we departed to our final anchorage destination of the evening. We were lucky enough to have a clear night, and watching the sun go down from the boat’s deck as we sailed away from the island was such a treat.
Waiting for us on the boat as we got back from the lobster bake was dessert, which was an amazing chocolate cake.
After furling the sails and anchoring for the evening, the crew filled the deck with lanterns, and we were free to enjoy the quiet of the night, surrounded by stars and moon, before heading to bed.
*Exact times will vary depending on your tour and specific boat.
Day 2
The crew has a much earlier wake-up call than the guests on the boat since they have so much to do, therefore, you may begin to hear some of them start their day earlier than you’d like to get up. This is where the earplugs come in handy.
During my cruise, most everyone arrived on the deck between 7:30-7:45a to enjoy morning coffee, tea, and baked goods before breakfast’s main course. However, you’re also welcome to be on your own schedule if you’re not a morning person.
Before lifting the anchor, breakfast was served around 8a again, and the familiar movements of the food train began as the main breakfast course emerged from the galley.
Much like the day before, around 10 a.m. it was time to once again hoist the sails, and if you can believe it, you gain an even deeper appreciation for the work it takes to set sail. Watching the process unfold from start to finish twice a day, over multiple days, makes it clear that the crew’s dedication isn’t just about hard work – it’s about a genuine passion for keeping this time-honored tradition alive.
During our second day, we unfortunately experienced quite a bit of wind, which made the bay choppier than normal. I’ll talk more about seasickness later in the post, but generally, it’s not normally an issue. However, this was a day I chose to preventatively take Dramamine and Pepto-Bismol, just to be safe. Thankfully, I was fine throughout the entire day, as long as I stayed up on the deck.
After a day of sunshine, curry for lunch, brisk winds, cruising by a lighthouse, and faring the rougher-than-normal waters, we made it to our final destination, which was Pulpit Harbor by North Haven Island. Pulling into the harbor, we were greeted with calm and protected waters, shingled houses tucked behind pine trees, and boats anchored in the harbor.
After dropping the anchor, the crew and volunteers began the process of furling the sails once again to prep the boat for the overnight stay on the water.
This is also where we were served our final dinner of the cruise, which included various kinds of pasta, fresh salad, and homemade focaccia. I honestly still think about the seafood pasta and focaccia.
After dinner, the captain lowered the skiff, and took anyone who wanted to go for a walk on the island to the shore. The twilight walk was a great way for us to stretch our legs and explore a new destination in coastal Maine.
During our last evening on-board, the lanterns once again illuminated the deck, and we were treated to some live entertainment: Captain Tyler and singer/songwriter Reese Fulmer performed original songs with their acoustic guitars, and Captain Tyler read some of his favorite excerpts from books about New England and life on the water. It was the perfect way to end the evening.
Day 3
The final day of a 3-night cruise is a half day, as you’ll come back to the dock by late morning or early afternoon.
Our last morning on-board, we woke up to a misty and overcast sky, which was honestly rather perfect and fitting for a New England adventure. The crew hung a tarp over the main portion of the deck to keep the light drizzles of rain away as we sipped our coffees and teas.
Our final breakfast of scrambled eggs with crispy potatoes felt so comforting on the atmospheric morning. And the maple doughnuts were another fantastic addition.
Shortly after breakfast, we began to return to the dock, enjoying classic, moody New England weather along the way. We did get lucky, in that it didn’t fully rain, so enjoying this other side of the region’s famous weather was a nice change of pace from our bright and sunny days.
Pulling back into the harbor, we were greeted with familiar views of Rockland Breakwater light and boats in the harbor, which signaled our journey had come to an end.
And before we knew it, we were back where we began at the ship yard, packing our cars with our bags and incredible memories.
Where To Stay Before & After Your Tour: The Logistics
If getting to the dock requires a longer journey on your part, I recommend staying a night nearby the night before, and also, a day or two after – so long as your schedule allows. Since tours begin around dinnertime on the first night, and conclude by late morning or early afternoon on the last day, this isn’t necessary, but it’s a lot easier if you have a longer drive or journey to get there.
Since your tour will depart from Camden or Rockland, you’re in such an incredible area to explore more of the Maine coastline, as these are some of the best towns to visit in the Midcoast region of the state.
You’ll find more hotel options in Camden, and that’s where I usually stay when in the area, but you truly can’t go wrong with either town.
My favorite hotels in Camden are:
→ The Norumbega: A renovated castle which provides a luxurious and unique experience.
→ Camden Harbour Inn: A cozy inn with a fantastic restaurant on-site.
→ Camden Riverhouse Motel: The best budget-friendly option in town.
All of these recommendations are walkable to the town center for shopping and dining.
My favorite hotels in Rockland are:
250 Main Hotel: Located on the main street, and offers modern rooms with tons of amenities.
Island View Inn: A short drive from Rockland’s downtown, you’ll enjoy water views and an outdoor pool.
Samoset Resort: A high-end resort with a golf course, spa, dining, ocean views, and a short walk to Rockland Breakwater Lighthouse.
⛵️Ready to book your windjammer tour?
Visit the Schooner American Eagle website here,
and the Maine Windjammer Association website here to see the entire fleet.
Maine Windjammer Tours: Answer Your Questions
What To Pack
American Eagle will provide you with a packing list, which I found very helpful, and followed pretty closely. As mentioned, you definitely want to pack smaller bags, as storing a large suitcase in your cabin will be more difficult. I ended up with two small duffle/tote bags, plus my camera bag, and everything stored perfectly under the bed in my cabin.
Here’s everything I packed that I would recommend:
Clothing: Pack in light layers, and check the forecast a few days before leaving. My tour was at the end of August, and it was a little chillier than average, which I loved. Pants, t-shirts, jackets, and sweaters were all helpful for me, but I would pack shorts if it’s forecasted to be warm and humid. I’m also really glad that I packed my waterproof rain jacket, which came in handy the last morning when there was a light rain.
Pajamas: You’ll have to walk to the bathroom, so you’ll want to wear something you won’t mind other people seeing.
A hat that stays on your head: This was on the American Eagle packing list, worded just like that. So, I packed the only hat I own with an adjustable strap. And it was the best thing to have on the cruise. One passenger during our tour lost a baseball cap, so you’ll definitely want something that will, in fact, stay on your head. I felt a little dramatic for having such a big sunhat, but it helped so much by keeping the sun out of my face during the day. I usually switched to a baseball cap or knit beanie once we anchored or in the evenings when the wind died down. The sun hat I wore during the tour is this one, which I love.
Toiletries: Stick to the basics. I just brought my usual face wash, tooth brush, tooth paste, and night moisturizer (since the evenings were chilly and my skin definitely felt it). I also packed sunscreen for my body, and a tinted SPF moisturizer for my face to wear during the day, which I applied each day of the tour. I left all other toiletries and make-up behind. They also provided shower gel, shampoo, and wash clothes for the shower. This is one area I would really scale back on because your bathroom spaces are very, very small.
Shoes: I mostly wore my Vessi waterproof sneakers. In fact, I think that was all I wore the whole trip, even though I also packed sandals. Just be sure that whatever shoes you pack are appropriate for being on a boat (make sure they won’t leave scuff marks, and they have some traction).
Seasickness medication: You probably won’t need it, but I did bring it just in case. See the next section below for more information.
Any other medications you take: Definitely don’t leave those behind! I also made sure to have over-the-counter stuff on-hand, like ibuprofen, just in case.
Your camera: I mean, for obvious reasons.
The right phone charger: I didn’t know this until after I had boarded, but thankfully, they had extras for us to use! Most chargers in the cabins for the entire fleet use the cigarette light-type chargers (that you see in cars). If you’d like, you can buy one here before your trip, or ask beforehand if they have extras for you to use during your trip.
A book or journal: To have something to do during the daytime sails.
Swimsuit and towel: I didn’t need these, even though I packed them, but that was simply because it was just colder than usual during our sail. These quick-dry towels from Dock & Bay are perfect – lightweight, fold up very compact, and they do dry fast.
Reusable water bottle: I packed my Swell water bottle just to stay hydrated between meals, and since all the water on the boat is potable, it was easy to refill in my cabin.
A small travel fan: I always travel with this one from Amazon, but I didn’t bring it with me, just because American Eagle provides fans in each cabin. However, you’ll want to check with your specific boat to see if they provide fans or not.
Drinks: If you’d like to have your own drinks for the tour, they provide a nice big ice chest on-deck. It’s accessible to everyone, and a few folks brought their own seltzers, wine, beer, etc.
Waterproof pants: This was on the American Eagle packing list, and I didn’t bring them, but did want to mention it. I don’t think I saw anyone else in waterproof pants, either. The captain did say these were mostly for days where it rains, so you don’t get your pants wet when you sit down. They covered the deck in tarps on our one rainy morning, so this wasn’t an issue during our sail. They would come in handy, however, if there was a downpour.
Cash for the crew gratuity: It’s customary to tip the crew about 10-15% of the total trip cost, but this is discretionary.
What About Seasickness?
My absolute number one hesitation is going on this tour was seasickness, and I’m very prone to both motion sickness and seasickness. However, I was assured prior to the sail that it’s rarely an issue, since the tours always have land in-sight, meaning you’re sailing in calm waters.
I found this to be true, and it does kind of depend on your luck. The second full day of our tour, as mentioned, it was pretty rocky. The winds were strong, so the schooner was definitely moving around quite a bit. I did take both Dramamine and Pepto-Bimol preventatively (not medical advice, just something I know helps me). And I was fine as long as I stayed up on the deck. Heading down to use the head or grab things from my cabin was when I started to feel a little “off.” I quickly felt normal again after heading back up to the deck.
All things considered, I was skeptical about how I would feel, but it really wasn’t an issue for me. I would pack seasickness medication to be safe if you’re prone to it.
How Many Days Are The Tours?
Tours are generally between 3-6 days, and which you choose is personal preference.
Where Do Tours Depart From?
Either Rockland or Camden in Maine, which are both very close to each other. It will depend on which schooner you reserve. Both towns are fantastic to explore, as mentioned.
What If I Have Dietary Restrictions?
American Eagle was amazing at accommodating dietary restrictions. I truly can’t speak more highly to how sensitive they were to this. They did a great job accommodating a few different ones during our tour, and everyone always had options. For those with allergies, they also did a fantastic job of keeping foods separate to prevent cross-contamination.
I’m Traveling Alone – Will It Be Awkward?
I traveled solo for this tour, and I didn’t find it awkward to be there alone. However, I also travel quite a bit by myself (including to places in Asia and Europe), so I’m pretty used to it. If you’re looking to book a schooner tour as a solo adventure, I’d recommend it! Everyone was very friendly, and there were plenty of opportunities to chat with people, and also have alone time.
I’ve also looked up reviews of the different tours, and I’ve seen that many folks have booked tours as a solo excursion, so I would not rule it out.
Who Are Maine Windjammer Tours For?
Honestly, just about anyone! During my tour, there were guests ranging from college age to seniors, and everyone in between.
The most important thing to know is that windjammer tours are really all about the experience, not the accommodations. So, you have to be willing to trade in some of the usual comforts you’d expect when staying at a hotel, but the experience of sailing along Penobscot Bay is what it’s all about.
However, if this is something that worries you, you can also book the 3-night tour, which is the shortest they offer, which will allow you just enough time to get your sea legs, and see if you can handle a longer one the next time.
But, as someone who was nervous about sleeping conditions and such, I absolutely loved the tour, and would 100% do it again.
What About Wifi?
There is no wifi on-board, so you should be prepared to not have service for parts of the trip, which is half the fun.
I have Verizon, and I had service probably 70% of the time up on the deck, and maybe 40-50% of the time in the cabin. For safety reasons (not that there were any safety concerns, I just do this out of habit when traveling alone), I would text my husband where we were, and when we were leaving. That was more for my own peace of mind, and not really necessary.
That’s A Wrap On My Maine Sailing Experience
And there you have it – the recap of my experience aboard the beautiful schooner American Eagle for a memorable 3-night windjamming tour along Maine’s stunning coastline.
I truly can’t recommend this experience enough—the food was fresh and delicious, the scenery endlessly breathtaking, and the sense of history made every moment feel special. Sailing on a historic schooner is unlike any other kind of travel: it slows you down, connects you to the water, and leaves you with memories that will stay long after the sails are lowered.
