Part 1: Sailing Cruises on Historic Maine Windjammer Ships

Join us to learn about the wonderful and unique world of Maine Windjammer cruising and why it’s nothing like traditional cruises. This is part one of a two-part series designed to help you understand what these overnight schooner vacations are really like.

For photos, visit our Maine Windjammer trip report.

We explain what a windjammer cruise is, where these historic sailing ships travel along Maine’s rugged coastline, and how the Maine Windjammer Fleet operates. We touch on its nine different ships, including American Eagle, Angelique, Grace Bailey, Ladona, and more to discuss who this style of cruising is best suited for.

We also set expectations around the cabins, Maine’s summer weather, cruise lengths, and getting to Camden or Rockland for embarkation. Island hopping, historic ships, cold ocean air, and lobster dinners: if you’re curious about unplugging, hands-on sailing, and experiencing Maine from the water, this is an idyllic escape. Part two covers life onboard, food, packing, pricing, and extending your trip in Maine.

Chapters

• 0:35 Introduction to Maine Windjammer Cruises
• 3:02 Precisely Where Maine Windjammer Cruises Sail
• 4:41 The Fleet of Windjammer Ships
• 8:38 Expectiations: Who Should (& Should Not) Consider a Windjammer Cruise?
• 14:28 How Historic Are These Ships?
• 17:18 Sailing Season & Itineraries
• 18:31 Ideal Amount of Time to Cruise
• 20:50 Onboard Cabins & Spaces
• 24:10 Where in Maine You Need to Be for Your Sailboat Cruise
• 26:15 First Hours After You Embark
• 26:36 Listen to Part 2 for More Valuable Maine Windjammer Info

Transcript

Dan (00:34)

Welcome to Small Ship Cruise Talk.

Today, we’re going to be talking about Maine Windjammer ships. The historic ships, one might say, that sail off the coast of Maine and off the eastern coast of the United States.

So last week we discussed what we're looking forward to in 2026 and on that list was our Maine Windjammer trip. So we thought this would be such a great opportunity to talk about Maine Windjammers and the cruise— our experience— and then kind of what to expect when you book and sail with Maine Windjammer.

It's such a unique experience that this is going to be two episodes because we really are going to drill down into the details and this is something you want to know what you're getting into because it's very different than other cruising.

Mikkel (01:25)

Yeah, it's a small ship cruise experience we love, but to your point, completely a very different experience. So today you will find out what a windjammer cruise actually is and where in Maine, Maine windjammer actually sails. You're going to learn more about the fleet and what a windjammer is anyway. Who should consider this kind of cruise and who should probably not go on this kind of cruise, which is equally as important. And also cruise options to expect in terms of itineraries, the length of the sailing, how long are these typically, the weather considerations, as well as when these overnight sailing cruises operate. You're going to find out what the onboard accommodations are like. Very important. You definitely want to hear that, so there are no surprises. 

And also some tips and info about getting to Maine and back, with things to consider for these cruises because of course getting there is really important to get on your ship. And then just a look ahead for part two. Next week we're going to discuss day-to-day life on a windjammer ship during your cruise, what the food is like with some lobster insights—lobstah!— dress code and the onboard vibe as well as what to pack. We're going to talk about the kinds of specialty cruises Maine Windjammer offers, the cost of these cruises and where that value is with them and tips for extending your trip in Maine. So let's get into where these Maine Windjammer cruises take place besides the obvious of in the state of Maine.

Dan (03:03)

When you jump on board a Maine Windjammer, you're going to be sailing along the rugged island-dotted coast of Maine, which you know in the name it makes sense that it would be in Maine. However, what a lot of people don't expect is just how many islands there are off the coast of Maine. And there's some little ones, some big ones, they come in all sizes up there. But these ships and these cruises really take advantage of those islands and you'll visit some of them, definitely not all of them, and each one has a unique experience.

Mikkel (03:37)

Yeah, it's perfect for this type of sailing. I didn't know until our first Maine Windjammer cruise that there is actually a Gulf of Maine. Right? Did you?

Dan (03:45)

It's gonna become the Gulf of Canada.

Mikkel (03:53)

Haha. (Sigh.) Okay. So, the Gulf of Maine, did you know that there was a Gulf of Maine? I did not. 

Dan (03:58)

I did not.

Mikkel (3:60)

Yeah. So that was a good geography lesson. And like you said, the beauty of the rustic coast, small islands, places that you'll be shown on the map. The captain will probably show you on a printed map.

Dare I say, not a digital one, which is really nice. Reminded me of Voyage of the Mimi, if that rings a bell with anyone. You don't know that movie? It was like we watched it in school about sailing. I think Ben Affleck was in it when he was like a teenager. Yeah. Put that on your Netflix list. So let's talk about the fleet in general. So now that we know where it sails...

Dan (04:25)

No. Hmm, I have to look that one up.

Mikkel (04:41)

There is a collection of nine schooners, or you could say eight schooners plus one windjammer ship. even after clarifying what a windjammer ship is, I would say the windjammer ship we're talk about, I'm going to name all of them in a second, is also a schooner because it has two masts.

The ships in the fleet, which I'm only gonna name quickly because maybe you're listening and you've been on Maine Windjammer, so this is a bit of a trip down memory lane for you, or you've been on it like us and then you have your eye on another ship to experience an additional schooner the next time you sail, or maybe a friend went and you're like gonna think, once I name it, yeah, that's what my friend went on. So the ships in the fleet are Angelique, American Eagle, which we went on, Grace Bailey, which we are going on next time, Heritage, J. & E. Riggin, Ladona, not to be confused with Madonna (different), 

Dan (05:36)

Different.

Mikkel (05:42)

Lewis R. French, Mary Day, and Stephen Taber. These are historic, gorgeous, well-maintained ships. They're generally around 100 feet long, give or take. They carry anywhere between 17 and 27 passengers. It's very specific to the ship that you're going to be on. They are independently owned and operated and together they all operate under the brand of Maine Windjammer fleet because a rising tide lifts all ships, right? In terms of marketing and the captain is very often the owner of the ship. 

And the minimum age of the people on the ship varies but there is a minimum age of usually between 12 and 16. It depends which ship you are on.

Dan (06:24)

That's a good point to bring up. They're all independently owned and every ship is different. So every itinerary is going to be slightly different and every experience is going to be different. So it's not like jumping on a Viking ship where it's very similar on the Rhine and very similar on the Danube. And, you know, you know where the coffee bar is on the Viking ships. This is completely different than that.

Mikkel (06:47)

Completely different. Speaking of the unique experience, what is a windjammer ship anyway? So I briefly touched on that it has two masts with sails. But the Maine Windjammer association website has a really helpful article about this. And first, they are traditional sailing vessels, it says. So, they're traditionally rigged, which means that most of the work can be done by hand, which you were definitely enlisted to help with because of your height and your muscles.

Dan (07:23)

great

If you cruise with Maine Windjammer, you will be asked to help out. This is not a spectator sport per se. You are actively involved in the sailing process.

Mikkel (07:37)

I love that you said that. It is an active participation cruise. You don't have to help, but you are not only encouraged, but you are asked sometimes. If you really don't want to help, you can just tell them, tell the crew ahead of time that you're not interested in helping. Sometimes you don't have the strength, or I don't know, if somebody goes on that has Parkinson's, let's say, I'm just thinking of some of the people in our family.

Or balance issues, but they've decided to go on and we'll talk about who this cruise is good for and not good for. But of course they are sensitive to that. So you are encouraged or asked to help out, but if you don't want to, you don't have to. The Windjammer cruises started in Maine and schooners were everywhere until they weren't. And I think one of the coolest things is if you are into history, how amazing is it to be on one of these historic, masted, sail-rigged vessels that were used for shipping and fishing and everything in yesteryear.

Dan (08:38)

Let's talk about who the ideal cruisers are. Who wants to do this? Because it is a different experience. I would say

Mikkel (08:44)

Mm-hmm.

Dan (08:47)

our first cruise with Maine Windjammer, there was a lot of sailing enthusiasts on board. There wasn't that many guests on board, but there was quite a few that maybe they had a boat and they no longer have a boat, or they just love being out on the water and sailing in a traditional sense of sailing.

Mikkel (08:52)

Mm-hmm. Mm-hmm.

And to your point with sailing, I would say there's really something special and magical about when the sails are raised by the crew and maybe with your help too, and you hear the wind hit those sails. Now all these boats have an engine, just in case, but they try to use the sailing power as much as possible. 

And even though we haven't been sailors, you know, historically, I'm proud to say that my grandfather and my father both sailed. My grandfather owned a sailing ship. And it's part of why I love going to connect with that spirit of the ocean and of the sailors. A lot of the captains and their families have some sort of maritime tie that's really fun and interesting to hear. So I completely agree.

Like you said, it's for people who love sailing but maybe don't own a boat or maybe they do and they just want a bigger boat to go on or with a crew and with other people who feel similarly about them. I would also add, if you don't know if you like sailing, if you don't want to necessarily buy your own boat, but you have an inclination that you might love it, this is an awesome way to try it out with very low risk.

Dan (10:29)

Right. Yeah. So I would also say this is good for couples, singles, and then also families, but understanding that the families may be split up 'cause the rooms are very small. So you might have to purchase a couple rooms if you're bringing a larger family also to note, just watch your age limitations and restrictions for each boat 'cause they are different.

Mikkel (10:50)

And I think on the note of singles— they have cabins that are just for one person. You pick the cabin once you book. It's not like you're just picking a suite class on a big ship. The ships are small. There's 24 people max, and some of those rooms are double, and some of them are single. So,

Yes, I agree. They're totally great for singles. Additionally, and we'll talk about the cost more next week, but just a note on the singles, it's not like a big cruise ship that it's based on double occupancy. It depends on the ship, but it's likely priced per person. So that's an advantage of these cruises. It's also great for nature and outdoor lovers.

These are two decks, these ships. And you are on the top deck 90 % of the time. And the other 10%, you're on land, I would say.

Dan (11:38)

Yeah, you are definitely out in the elements and you are engaging with the outdoors and with the water. Well, not in the water, but you are right there.

Mikkel (11:47)

You'll definitely be on the water. Also, people that don't need luxury for a few days. Let's be clear, this is not a luxurious experience. All nine ships have their own interiors and personality. Angelique even has like a reddish maroon colored, I would say brownish sail that makes it extra unique. But it's not luxurious. I would say out of any of the ships, maybe Ladona and Grace Bailey, are two of the more… How would you describe it? Shabby, chic feeling. Modern's not a great word, but

Dan (12:25)

Right. Yeah, due to the historic nature, there's only so much they can do with the interiors. 

Mikkel (12:30)

Or want to, yeah.

Dan (12:32)

Right, right. So you're not gonna find luxury, but if you are interested in meeting new people and spending a lot of time in close proximity with those people, is gonna give you that opportunity. So, you know, you roll the dice with any cruise. You may or may not like the people that you're on the cruise with, but you are going to be up close and personal with everybody else that's on these cruises.

Mikkel (12:55)

On that note, there's no Wi Fi. So you are going to enjoy nature, enjoy each other, enjoy talking to the captain and the crew, the scenery. You can enjoy some alone time in your cabin like you know, I retreated for some time when I just needed a break or a nap or whatever. But there's no Wi Fi. So we'll talk more about what that means for your packing lists and some things you can pack to entertain. But they're not great for also people with

Dan (12:57)

Right. 

Mikkel (13:22)

serious mobility issues because more than likely there is a ladder that goes between deck one and two for you to get up on the top deck. It's not like a normal staircase on most of these ships so you need to feel comfortable with that going on your own.

Dan (13:40)

I would also say if you're looking for a luxury experience, this is not it. This is a little bit like camping, but on the water.

Mikkel (13:47)

Yeah, we describe it as glamping on the water for sure. 

Dan (13:49)

Right.

Mikkel (14:14)

We've we've had those conversations many times. Additionally, if you have vertigo, it might not be the cruise for you. Now, even if you think to yourself, I go on other cruises, I'm fine. Totally up to you and your call.  However, it is a sailboat and you don't know what the wind is going to bring or the sea and it is a smaller vessel. So it could affect the ship more. These ships do not have stabilizers like you know, luxury expedition ships. So keep that in mind.

Dan (14:18)

Yeah, you're gonna feel the ocean and I do get seasick and I did not have a problem on our particular cruise, but it is something to keep in mind.

Mikkel (14:28)

So speaking of how special it is to be on these working sailing ships that are not replicas, they are originals.

I did want to point out some of the years that these ships were built in. Now on more modern ships, you might think to yourself, well, it was built in 2000 and now it's 2025. So it's 25 years old. When was the last time it dry docked? If you're used to traditional cruising, just put that out of your head. This is not apples to apples.

These are ships that part of the reason people sail is what we mentioned before, the history, the feel, the wood, the craftsmanship you can see in these original vessels. So Ladona was built in 1922. Louis R. French was built in 1871. Mary Day was built in 1962. American Eagle was built in 1930. And we had the pleasure and honor of sailing on that ship for a few nights and it was originally a fishing vessel. And do you remember there were photos, black and white photos of when that ship was a fishing vessel?

Dan (15:36)

Yeah, that was the really the interesting part because they leaned into the history and the ship itself was was part of the experience, right? Like so many of the other cruises you go on it's like it's just your means of transportation to get you to your your ports and you know to your destinations and things but this was the ship itself was part of the experience

Mikkel (16:03)

I think also when you're thinking of dying traditions, craftsmanship comes up a lot. And how incredible to be on this ship that was built by hand with wood carvings. You can still see some of the incredible, I want to say like mermaids at the front of the ship. It depends on the ship and

Dan (16:22)

All right, yeah.

Mikkel (16:24)

But just some of that, like we were saying before, the nod to traditional sailing in the 17th and 18th centuries that if you truly love the ocean and that connection to it, there are a few other cruise experiences that are going to give you something like this. I think of Windstar. I think of Star Clippers that also have sails, but it's not like this because those vessels are over 100 people to the mid 300s. This is less than 30 people.

Dan (16:59)

Right. And they all have mechanisms to help lower and raise the sails. Right. Right. So that's, that's a huge difference there.

Mikkel (17:05)

Right, the Windstar and the Star Clippers. Right.

Sorry to clarify, Windstar does, but Star Clippers, I think, is by hand. Yeah. We should actually do an episode on Star Clippers one day.

Dan (17:13)

Right. good.

Mikkel (17:19)

So the sailing season, let's talk about that. You can’t sail in December. 

Dan (17:24)

Right.

Mikkel (17:25)

Again, we're in Maine. We are in Maine. We sailed in June the first time. So the sailing season runs from May through September. September, of course, brings that incredible fall foliage, which, of course, your best guess is when you're going to book for what the peak foliage is. It varies year to year, just like the cherry blossoms. But let's have a reality check on the weather. You're going to sail during summer, however...

Dan (17:51)

…you better bring a jacket or, three. It is chilly on the water in Maine and you are going to feel it. And especially because the boat itself,

Dan (18:03)

in our case, it was an old fishing vessel. So it wasn't really built for warmth and comfort. It was built to go fishing. So going back to that rustic feeling— you are going to want to bundle up and make sure that you have weather-appropriate clothing.

Mikkel (18:16)

Right, so stay tuned next week for our part two when we talk more about that and tell you what we were glad we packed before and we will be packing more of for this trip during the summer when we go back on Maine Windjammer on Grace Bailey.

Cruise lengths and itinerary. So also uniquely, these are overnight cruises, but they really range from one to seven days in most cases.

The most common, I would say, are in the three to five, maybe even six-night range. If you are somebody who's going to want a luxurious shower on day five, stick to three or four nights. I would say one to two could get your feet wet, especially if you maybe have some form of motion sickness or vertigo and you want to try it out. But I think the sweet spot is really three or four nights. What do you think?

Dan (19:05)

Yeah, I think that's the best way to experience it and then you can always go back for more if you want longer stays, but you're stepping out of your comfort zone, right? So like we said earlier, there is no Wi Fi and that type of travel may be a bit jarring or different for a lot of people. So I would say ease into it.

Mikkel (19:29)

Especially if you're cruising with your teenage children. Right. I mean, you can have your cell phone, of course. And when you get on one of the islands, you can see if you have service. But it really depends where you are. You might if you're in Stonington, where a lot of people are, or you might not if you're just on this remote island. I remember we had like an awesome hike, the two of us, on one island that I couldn't even tell you the name of. But there was definitely no cell service there. But that's part of the beauty of it, you know?

Dan (19:32)

Right? There will be a revolt.

Right. Right.

Mikkel (19:59)

But also, if you are like, "I know I love sailing, I really want to commit to this." There are longer itineraries in some cases. They're few and far between, but there's like a 10-day cruise on Angelique that is taking cruisers from Boston to Camden, Maine. So from Massachusetts to Maine. And, you know, just be cognizant of how the cruise length might affect your experience. You always say...

What do you say? "The journey has left me before I left the journey." If that might happen, check out before then. Book a shorter one. If you've never been on it, start shorter and then you can always book longer the next time. Just know thyself, right? So next week, we're going to talk about the cost of these cruises and what they include and don't include. So of course, the length of your itinerary affects that.

Dan (20:28)

Alright.

Mm-hmm.

Mikkel (20:51)

All right, you touched on a little bit about what accommodations are like on board. You set the expectation that this is not luxury. But let's talk more about the bathroom situation, the size of the cabins, and why simplicity is part of the charm.

Dan (21:08)

Yes, I finally get to use some potty humor. Let's do, let's do this. No, no. So your cabins are going to be pretty small. In our particular cabin there was a sink. Correct. A sink in the room, but there was a shared bathroom and shared shower. I'm using air quotes here because the shower was mostly a bucket or bin and a hose and no hot water.

Mikkel (21:10)

⁓ gosh. On our particular ship, yeah.

Mm-hmm.

Dan (21:35)

So think of it as a stand-up sponge bath, I guess was the best way to put it.

Mikkel (21:40)

Let's just say between how cold it was on deck and people being able to just, you know, spot clean if they wanted in their room with the sink. There weren't a ton of people showering. And one of the most amazing showers I've ever had was when we got to the hotel in Bar Harbor after we got off the ship. That's a story for next week, perhaps, when we talk about extending your trip in Maine. But the toilet, I think there were two toilets for the crew and 25 people.

Dan (21:56)

⁓ yeah.

Mm-hmm.

Mikkel (22:07)

It was never a problem. We never had a wait, but again, not luxurious. Think glamping on a nice sailing vessel. Think, you know, historic sailing vessel ship. I will say that all of these ships, if you go onto the website you can look at all of the ships in a gallery of images. And I don't book anything without seeing the photos. So those are super helpful.

Dan (22:31)

We talked about the shared bathrooms and the shared showers. Now, American Eagle there was a nice cozy functional community space right by the kitchen. So that was nice to get warmed up because

Mikkel (22:41)

Mm-hmm.

Dan (22:45)

the cook was making dinner or something, you could feel the heat coming off the stove. But it was also a great place to eat dinner, A. But, also if you wanted to play cards or have a conversation or anything like that, it was very… How should I say? It was very warm and welcoming space. right? Plus they had the historic photos up and things like that. So it was a nice, a good little place to chill out.

Mikkel (23:05)

It was literally warm because there was a fire stove in the galley.

Mm-hmm.

Yeah, I'm just thinking of the ship overall. And between that area, it was almost like a dining room, sort of. But I mean, really tiny, like you referenced, with the small stove. And then there was another area, if you remember, that we were in very briefly. It was almost like the captain's quarters. Actually, the captain— I think he did sleep there. It's kind of like a living room and then his bed just had a curtain that can move to, you know, make it private or not. He wasn't in there, but he, you know, opened it up to people. And then there's also the top deck that was very popular to hang out and varying levels of covered spaces and not. But again, it's mostly an open deck. 

We have a link in our show notes to our trip report: Details of our American Eagle experience, so if you click through there you'll see the Maine Windjammer website and you can see photos of everything laid out in a gallery of images per ship.

All right, well, you have to get to Maine. So obviously, if you live nearby, you can drive. I think most people are probably going to fly up north to get there. Most of the windjammer ships embark from one of two cities, either Camden or Rockland. They're small towns, very charming. I would say if anything struck me about coastal Maine, it was just how charming and quaint

Dan (24:12)

How do we get there?

Mikkel (24:35)

one city was to the next and we were just hit with this beautiful charm. So I would say you can fly into Portland, Maine or Boston, Massachusetts. The benefit of flying into Boston is that you're probably going to have more options for flight itineraries and schedules and maybe it might even cost a little less because Boston Logan Airport is international, major, and just has more flights.

Dan (25:00)

Now if you do fly into Boston, you're going to have to rent a car to get up Camden or Rockland. So, just keep that in mind. Like we said, you can also fly into Portland, Maine, but you'd still need to rent a car to get to the port.

Mikkel (25:14)

Yeah, the benefit of flying to Portland, Maine, is that it's closer to the ports. And that if you don't want to rent a car, it's kind of like you have to do the cost-benefit analysis. 

You might be able to fly into Boston, but you probably either definitely have to rent a car or if you're going to take a shuttle, it's going to cost a little more because it's further. If you fly into Portland, maybe it costs a little more. Maybe it doesn't. I mean, it depends on the flight path and the dates and everything. But if you fly into Portland, you might be closer to the port, but you can hire a private car. So, you know, just keep those things in mind. This is all just to make you aware of it.

Dan (25:47)

Right, because you will have to keep the rental car at the port while you're on the cruise.

Mikkel (25:52)

Excellent point. So if you do a four day cruise, you're paying for all those days, not for the parking. The parking is included. You know, it's free, but you're paying for the car to sit there. 100 % good point. And that's exactly what we did when we were on American Eagle, if I remember correctly, right?

Dan (26:02)

Right. Yeah.

Yep. Yeah, we rented a car and it broke our heart to pay for it to sit there, but that's what we did.

Mikkel (26:16)

And you know, another point that it makes me think of is that when we got there, you board the ship in the afternoon. It doesn't go anywhere. You have breakfast the next morning and then you sail away. I think that's true of most of the ships, if not all of them. I'm not going to pretend to know every single itinerary on all nine ships, but it seems to be the case with most of the ones we've looked into.

This is a great place to stop our part one episode and look forward to next week when we get into more planning logistics. We talk about extending in Maine, which is 10 out of 10, I would recommend.

Dan (26:52)

Yeah, Maine is a magical place and there's much to explore and a cruise and seeing it by the coast is one way, but then pick up that rental car that you've been paying for and start to explore the interior of Maine also. Definitely highly recommend.

Mikkel (27:07)

This has made me so excited to really be a part of this maritime community again this summer. And I love that Maine Windjammer provides that option without all the costs of us having to own a boat, maintain that boat, which is no small feat. You know, when these boats are off for the season and they take them out of the water, I am certain that they are constantly working on them and painting them and doing all the maintenance that really

Dan (27:20)

Alright.

Mikkel (27:33)

is needed for a ship that is in saltwater all the time. Okay, so that just leaves me excited for next week when we talk about the cost, we talk about the packing, we talk about the food. I'm so excited. I want lobster right now.

Dan (27:48)

So until then, make sure that you subscribe and if you have a question or you want to leave a review, we're always open to hearing from you, our questions and your comments really guide us on what kind of information we're bringing to what types of conversations we have. So don't be a stranger, reach out if you've got questions or comments and until next time, keep cruising.