Dan (00:35)
Welcome to Small Ship Cruise Talk. Today is part two of our Maine island-hopping adventure on Maine Windjammer sailing cruises. Fun fact, this is our 50th episode, so cue the horns and the music.
Mikkel (00:51)
Bum bum bum bum!!!!
Dan (00:53)
Yay to us. So thank you for all of you for listening, for rating and reviewing us, and then also your comments. So we love to hear from you and truly, you're the reason we do this. So what do you want to hear? What do you want to learn about? Let us know.
Mikkel (01:09)
My 50th episode wish is for you to share this with a family member or a friend who you think might like our episodes, any of them, including this one on small ship cruising. I also want to take a moment as we talk about part two of our Maine Windjammer overview between last week and this week and whenever you're listening to dedicate this to my grandfather and my father, both of who instilled their love of the ocean and of sailing with me and I am so glad you were able to have a part of that in some big and small ways too, Dan.
Dan (01:48)
Absolutely. So last week we shared part one of our Maine Windjammer cruises overview and this week we are going to jump in and pick up where we left off and really give you that holistic view of what to expect when you cruise with them.
Also want to call out that in our show notes there are links to three important articles that include photos and detailed experience of our cruise with Maine Windjammer and specifically on American Eagle. There's also a link to a downloadable packing list. So if you are going to be cruising with Maine you're definitely going to want to get that packing list so you know what to bring and what not to bring.
Mikkel (02:33)
If you are listening after July or August, 2026, you'll also find more information on SometimesSailing.com, our website, about our experience sailing on a Maine Windjammer ship, for the second time, on Grace Bailey.
All right, so enough about that. Let's get into what you're gonna learn today. If you are listening, we are gonna get into the day-to-day life on a Windjammer ship during your cruise, what the food is like, a personal favorite topic, the dress code and onboard vibe, as well as what to pack, which is very important. We're gonna share what we wish we would have packed last time and what we are packing for this time. The kinds of specialty cruises that Maine Windjammer offers (they offer some really cool ones), the cost of these cruises and where the value really is in our opinion and extending your trip in Maine. Don't forget to check out part one from last week when we talked about the fleet. What the heck is a Maine Windjammer ship? What's a schooner? Who is this good for? Who is this not good for? What you can expect in terms of length of the cruise and the itineraries and what the onboard cabins are like and also transportation to get to Maine and back. So that was last week.
Be sure to listen to both episodes. You don't have to listen sequentially. They're both very helpful. It's really up to you.
Day-to-day life: I would say the Maine thing to take away about day to day life on a Windjammer cruise is that it's kind of captain's choice and the captain does his or her best to go with the weather and what the wind is going to help, you know, literally carry the sails and for all the guests to have the best experience. You’re cruising mainly the islands in Maine. Some of the cruises go elsewhere like Boston or New York, but very few of them. So let's, for all intents and purposes, talk about within Maine.
Dan (04:26)
Let's dive into a typical day, kind of morning to night. As you sail in between islands, like Mikkel said, it's captain's choice. He or she is going to be trying to build the best itinerary they can for you throughout the day. So there's going to be some variance and there's going to have to be some patience. The weather is going to play into that a little bit. Especially when you talk about shore landings, so the hikes and exploring the islands and things like that.
Those things may change, but just know that your captain is going to do the best they can to make sure you're enjoying your trip.
Mikkel (05:02)
And a note on that: It's not like a typical cruise that, you know, it says day one, we're in Athens. Day two, we're in Croatia. Day three, we're in, you know, Venice. It's not like that at all. You're in Maine. You're going to see cool things. You're going to see quaint islands, charming towns. We went to Stonington. We have an article about that on our site. If you go to the Maine Windjammer cruise category, we went to Deer Isle.
These are just small working communities. If there's really a population at all, a lot of people have summer homes there. Definitely picturesque. There are purple lupine flowers just dotting the landscape all over Maine in the summer. There's blueberry shrubs, blueberry bushes. Blueberries are a staple there. And talking about the day-to-day, when you wake up, the cook or the chef on board is going to make that buffet breakfast for everybody. Everybody's going to help. Usually if it's up on deck, kind of a bucket brigade-style assembly line, right? Remember, like bring those dishes up. It's really communal, that community feel, that vibe, that "all hands on deck," everybody's chipping in.
Dan (06:02)
Right. Yeah.
Mikkel (06:12)
When you said shore landings, it reminded me of tendering. So if we anchored in the water, because you can't really pull up to port in most of these places, you get into a little rowboat that one of the crew members rows you to shore.
Dan (06:27)
And some of the guests help out with that rowing because I know I was doing some rowing.
Mikkel (06:32)
Yeah, yeah. So you'll have lunch on board. There's also snacks on board— the captain made sure that the chef was keeping us well fed. We'll talk about the drinks in our next portion of this episode with food on board. But there is also a lot of leisurely time. I'm glad that there were binoculars. We could spot wildlife, a lot of birds. A lot of birds.
You know, just enjoy the breeze, enjoy the shoreline as it goes by and the scenery. And then also like, you know, we'll talk about this in packing, but I was glad that I had my sketchbook with me.
Dan (07:06)
That's a great point because there was plenty of opportunity— there was cruising and there was exploring so that it was a nice balance of if you just wanted a day to relax or an afternoon just to chill out a little bit and watch the water go by you could do that but then also there was activities to do with hiking or going ashore
Mikkel (07:25)
Also, it's good to nap on the ship during the day. If you have downtime and you just want a little 20-minute snooze, that was nice. So I appreciated that. And talking to other guests. I mean, this sounds like nothing
Dan (07:32)
Sure, yeah.
Mikkel (07:40)
earth-shattering, but it's not. It's just really lovely and relaxing and a way to escape the day-to-day and do something simple. And that is really, I think, what encapsulates the day-to-day itinerary on board. Would you agree?
Dan (07:55)
Yeah, I would agree. You hear the term "slow travel" and this really falls into that category where
Mikkel (07:58)
Mmm, yes.
Mm-hmm.
Dan (08:03)
it's all about the experience.
It's all about being right there in the moment and enjoying the ship and enjoying the history and enjoying the connection to the water, to nature and to your fellow passengers.
Mikkel (08:15)
Yeah, I love that really being present and I think not having Wi Fi on the ship really helps in that regard. You know, I really love that. Yeah, watch the sunrise, watch the sunset, go on deck after a sunset to see the stars, that kind of thing. If you are craving more information about exactly what we did day-to-day, be sure to check out that article that Dan referenced— the trip report that's in the show notes.
Dan (08:20)
That was right. No doom scrolling.
Yeah.
Mikkel (08:44)
Let's move into another thing to expect on board, that lobster. I love that. So let's talk about the food.
Dan (08:51)
Food is... this was where I was more than pleasantly surprised. I wasn't... I kind of didn't know what I expected actually. And when we got there and we saw the stove— it's a wood fire stove, right, on American Eagle— and there was a moment of, "Uhh... what are we... are we gonna have hot dogs every day? what..." Right?
Mikkel (08:56)
Yeah, me too.
Mm-hmm. Mm-hmm.
On American Eagle, yeah.
Oh my god, the red hot dogs in Maine. Okay.
Dan (09:19)
Like, I didn't know what to expect, but then what Chef was able to do on that wood burning stove, small stove, like the size of my desk, like small. Right? What he was able to do and just the depth and breadth of the amount of food that came out was impressive, but everything was just, wow, so good.
Mikkel (09:27)
yeah, like Colonial Williamsburg small.
Mm-hmm.
Yeah, and with crew, was about 30 people. So cooking for crew as well. I mean, even chocolate chip cookies. Yeah. And don't you worry. There's coffee on the ship for sure. No one's going on this cruise without coffee on any cruise, you know? So the meals were buffet style, but buffet is not a dirty word. We have an episode that we talk about small ship cruising food. So definitely be sure to check that out. It was a couple of weeks ago.
Dan (09:49)
Right, yeah, a little surprise and delight chocolate chip cookies.
Yes. Right. Yeah.
Mikkel (10:11)
It was episode 37 where we talked about Cruise Myth Busting: Small Ships That Go Beyond a Buffet. And I would say that even if there is a buffet on small ships, which we referenced in that episode, like on Maine Windjammer. When I think of the cruises that had great food, Maine Windjammer stands out. And I always think of it and always
Dan (10:16)
Mm-hmm.
Mikkel (10:30)
think of Maine Windjammer.
Dan (10:32)
Yeah, that is interesting. It was, well, I think a lot of it was the food was made with love and you saw it being made and
Dan (10:40)
as we talked about in the last episode, and I'm sure it'll come up again and again, like you participate, right? So maybe it's setting the table, doing the dishes, you know, like you were actively involved and it...
Mikkel (10:49)
Yeah.
Dan (10:53)
for me it was like, I'm helping my grandmother in the kitchen, you know, and learning ⁓ little tips and tricks but also just seeing the love of labor that was going into it and then it being cooked over an open fire, the stove was fire, you know, it's not electric or gas. and So I think it was just a combination of a lot of those things and just smelling the smoke and you know the food. Yeah, it was it was a whole vibe.
Mikkel (11:07)
Yeah.
Mm-hmm.
Yeah, I really appreciate you bringing back all those sensory indicators of how fantastic this cruise was, including with the food. And like I alluded to before, there were snacks. I remember coming back from some landings, walking on shore, that there was a little crudité or a crab dip or a fish dip or...you know, we're on the ocean, so. Just a variety of hors d'oeuvres to keep us fed.
Dan (11:38)
Yep.
Mikkel (11:47)
The thing about the beverages that is interesting is that it's BYO, which you know ahead of time. They tell you that you could bring your own drinks on board. So whatever your poison is. I don't know about the restrictions. Be sure to check with your cruise line. We're not heavy drinkers. You know, we probably brought a few beers, bottle of wine kind of thing. But also keep in mind the length of your itinerary might only be three nights, four nights. So don't go overboard. But on American Eagle, they had like a cooler that we kept it all in. So that was great.
Dan (12:08)
Later.
Mikkel (12:15)
And of course, water and everything, you'll have that on board. Another thing that's a highlight is these Maine Windjammer cruises, they know everybody's excited about lobster, of course, if you eat lobster. So there is a lobster night and that's usually on land. That's usually ashore on some sort of beach experience. And if the weather is inclement, like it was during our cruise, we all used the benches on the top deck as kind of tables and it was one of the most memorable meals I've ever had on a cruise. The lobster was so delicious.
Dan (12:48)
Lobster was delicious, the atmosphere was fun. It was definitely a party and we were all cracking lobsters and it wasn't like one lobster per person. It was, "Hey, do you want another lobster?" And they were like...
Mikkel (13:00)
It was, I would say unlimited. I mean, it's not unlimited, but the amount of times they were asking us, they had so much. They literally got the lobster out of the ocean that day. Remember Captain John, who is now retired— American Eagle is in the hands of new loving owners. But Captain John put on his yellow rain suit, you know, like the overalls and the hat. He looked like,
Dan (13:23)
Gordon's Fisherman.
Mikkel (13:24)
Thank you.
Dan (13:24)
Yes.
Mikkel (13:25)
He looked like Gordon's Fisherman. He had the white hair, the white mustache. And we were like, "It's pouring. Where are you going?" And he looked at us like, "Of course, I'm going out to get the lobster. I'm rowing on this rowboat by myself." No cell service. I was like, how do we know where you are? I felt like a parent. Literally, into the fog, rows off, comes back with these lobsters, like thank you lobsters for allowing us to eat you.
Dan (13:40)
Into, into the fog. just, he rows off to get the lobster. Yeah.
Mikkel (13:54)
And we had soft shell lobsters, which I had never had before that. But the reason is because they can't be shipped because they're in between shells. They're molting, kind of like soft shell crabs. They were so easy to open and crack. And we're not "lobster people," per se. But I was after that. I mean, I couldn't believe how much lobster you had. For somebody who's not a big eater, like all these factors, you know, and it was just so delicious.
And they basically just steam it and give you a side of melted butter with it. It was *mwah* chef's kiss, one of the best meals I've ever had, for sure on a cruise ship. Just simple, fished with love from the lobster men and women, very few women lobster in Maine, but the lobster people and row-boated back into our ship from the captain and cooked by the crew with love, and it was just *mwah, mwah mwah* delicious! Thank you, lobster people.
Dan (14:49)
Yes. Thank you, lobster people. We appreciate you.
So we had lobster on the top deck and the vibe was friendly and casual, but the reason we had the lobster on the top deck was because of the bad weather. So let's talk about how you should dress yourself on board.
Lobster night, like we said, it felt like camping. It was supposed to be on shore. So no tuxes, no ties, no dinner jackets are necessary. This is a very casual, very relaxed cruise.
So there's no formal nights. There's no dress code. Choose very practical clothing over fashion and you want to be comfy, cozy and warm. So keep that in mind as you're packing.
Mikkel (15:35)
I was glad we had long sleeve options. I was glad I had a sweatshirt. I was glad I had jeans. I might've ended up wearing the same thing all days because we didn't pack enough warm weather clothes. We were there in late June and we thought, "Oh, it's going to be warm." And even if the forecast for Maine on land says one thing, you are going to want to account for 10 to 20 degrees less on the water.
Dan (15:45)
yeah.
Mikkel (16:05)
and wind. So things I am going to be sure that I pack for next time this summer: More long sleeve shirts, at least one more. It's only four nights, but one more. I am not kidding, I will pack a scarf and gloves, maybe even a little beanie hat. And I want to pack like little slippers for not the top deck, but for our cabin and just scooting around the interior deck.
Dan (16:35)
Yeah, I would say like flip-flops, something like that. Slippers are going to keep you warmer, but going to the bathroom, because it is a shared bathroom, things like that. I didn't really want to walk around in my socks.
Mikkel (16:42)
Mm-hmm.
Yeah, and most of the ships, if not all of them, send you a suggested packing list. So you're to want to pay attention, especially to the footwear that you're able to wear on the top deck. There are some rules about that to keep everybody safe. Definitely cozy, comfortable, practical. I'm going to pack leggings.
Let's talk about the sun. It's still sunny. So the days that the weather was good,
Dan (17:04)
Right.
Mikkel (17:06)
you needed sunglasses, sunscreen. It was a little warmer on shore, of course, when the wind wasn't in our faces. So you are going to want to be layered. You still need a t-shirt. You still need shorts, especially if you're going to extend your trip before or after on land, you want to pack in layers. Another thing I would say is a must is binoculars.
Dan (17:28)
Oh yeah, yeah. Because let's face it, there isn't a ton of things to be doing. There isn't a ton of things to do on board except look at the scenery. So if you're into bird watching or you're going to spot animals, sea life, and also animals on shore, and just taking in the views, definitely want to bring the binoculars.
Mikkel (17:48)
There might be some pairs of binoculars on board. However, the ones we bring are number one: ours. We're happy to share with other people as long as we see what we want to see first. And, secondly: they are better quality than any binoculars we've ever seen or been provided on a ship. We'll link those in the show notes. But keep in mind, it's also in our downloadable packing list. So that's linked in the show notes as well.
That is a freebie for you guys to download if you go to the article and just enter your info to download it. And then lastly, I would say, to your point, some leisurely things. I brought a sketchbook with a travel pack of watercolors. You're going to want to download any audiobooks or if you want to catch up on Netflix on your iPad, you're going to want to download all of those things before you leave your pre-cruise hotel that you book on your own if you're doing that or before you leave the airport or before you leave home.
Dan (18:41)
That's good call out.
It is interesting when you mentioned the watercolor on our particular cruise, there was a group of people all doing watercolors throughout the day and it was a themed cruise. So it's pretty interesting. It was fun to watch and kind of be in the middle of because we weren't there for the watercolor portion of the cruise, but it was just fun to be a part of that. But they got a bunch of other ones. Like what was that one?
Mikkel (19:01)
Mm-hmm, mm-hmm.
Dan (19:07)
Didn't you say there was a knitting or crochet cruise or something?
Mikkel (19:10)
Yes, I am a crafty gal, and I did think that the knitting and crocheting cruise was appealing. So these are cruises that are very much indicated when you go on the website of the Maine Windjammer cruise that is offering it— the ship in particular. But just in general, we wanted to mention that there are themed and specialty cruises. So in addition to the crafts —like watercolor, knitting, crocheting— there's themes around things like Maine lighthouses.
So if you are an artist, if you are a photographer and you're like, "Oh my god, the lighthouses! We're going to specifically go to these lighthouses. I want to book that," something to be aware of. There's also astronomy cruises, like for meteor showers. I've seen guided astronomy cruises in the past where they bring on an astronomer of some sort to educate everybody on board. That's amazing. And then always popular every year—
Dan (19:50)
Hmm. That's cool.
Mikkel (20:04)
you really want to bundle up and bring a coat for this—is the fall foliage cruises.
Dan (20:09)
Yeah. So interesting. I'm sure that we doing something for Sail 250, this summer. For those of you that don't know, that's a 250th anniversary of the United States. So, I mean, what better way to really experience that than with a historic ship.
Mikkel (20:25)
Yeah, completely. And it is January, 2026, early January when we are recording this. Some of the ships have a commemorative kind of sailing for the 250th anniversary of the United States. If you are listening to this past the summer, S.O.L. It already happened. ⁓ And if you are interested in that, I would look it up ASAP. They are on a waiting list for some of those. I know American Eagle has a waiting list
Mikkel (20:52)
because they are cruising into New York City for the largest flotilla in— you know, everybody says the best pizza, the best coffee— the largest flotilla in the history of the United States. I hope it is for everybody going and that sounds amazing and quite the sight to see.
So, that's just an overview of some of the themes that you can expect.
Let's talk about the cost and the value. So, like we've said over and over, this is a really unique experience that is not going to break the bank. Prices start at $795 per person, and these are priced per person, so it's not based on double occupancy, which is nice, especially if you're solo. Three nights could be, for example, $1,100 per person.
It varies depending on the ship, and it varies depending on when. So maybe one specialty-themed cruise is going to be a little bit more because they have to pay the onboard educator maybe. I won't pretend to know how that works behind the scenes, nor do I want to know the ins and outs of that. Four nights could be $1,300 per person. It could also be $1,700 per person depending on the ship and the itinerary, like if it's going on a regatta, for example.
The prices do not include gratuities. So you're going to want to account for a few hundred dollars for all this said and done. We haven't been on in a couple of years at the time we had to pay those in cash, but I would be curious to know if we can pay those kind of via Venmo or Zelle or on a credit card.
Dan (22:24)
Yeah, I almost think there was a Zelle or a Venmo option that they were talking about, but it wasn't available yet.
Mikkel (22:30)
It's interesting when the ships are sold to the next generation, it's really fun to see how they update the website. They update itineraries. They update info, which I've really loved seeing because as I said, the American Eagle captain retired and you know, a new couple owns it. So I think that is kind of a cool thing. And as the brand moves into the future, those are things to look out for to kind of modernize, but keep the history intact.
Also included is meals, know, the sailing, the activities. That's not going to be additional for you. Anything additional on land would be like if you buy souvenirs, if you go get a coffee yourself, you know, that kind of thing.
Dan (23:10)
That is an interesting point like there is nothing really to buy on board so you're not buying excursions, there's no bar. So really nothing hidden. At the end of the trip, you're not going to get a bill.
Mikkel (23:14)
Mm-hmm.
Great point. I think the value is really in the experience, not the amenities that don't exist, not upgrades, like you're saying. The experience and the hard, fast experience of the captain and the crew is really what you're paying for.
Dan (23:28)
Right. I think also the value is all the options you have. So all the different ships, all the different lengths of itineraries, the different itineraries themselves. You can really mix and match an adventure out of this and they have something for everybody.
Mikkel (23:40)
Mm-hmm.
Dan (23:50)
So it's nine days or three days or if it's kind of whatever you want your experience to be, there's probably an option for you.
Mikkel (23:52)
Mm-hmm.
I love that because you can also mix and match days and ships. So let's say you are on one ship for three nights and then you back-to-back with a four night cruise right after on a different ship. How cool would that be? Right? Like you're in Maine anyway, why not? Right? Especially if you're like, "I have a week and a half, I have 10 days, I can combine it with, extending my trip in Maine," which we'll get into momentarily. The last thing I just want to mention about the value and everything is that
Dan (24:08)
Hmm. Yeah, that would be interesting. Yeah. Sure. Yeah.
Mikkel (24:25)
you can book online. In some cases, you can book directly. So you just go to the Maine Windjammer ship website, depending on the ship: Ladona,
Grace Bailey, what have you. And enter your desired sailing date and cruise and the cabin type. So you're booking the precise cabin type. You're not booking the suite class. You're booking a double bed kind of, or solo cabin.
And you can enter your credit card in a lot of cases. In other ships, in other cases, you might have to fill out a form, and they'll contact you to book. It really is dependent on which of the nine ships you're booking. And then also be aware of the cancellation policy, which is also why we always say you know, you want travel insurance. These are small businesses. They are not banking on these cruises. They are just feeding their families and doing what they love.
So read the cancellation policy. A lot of them are like, if you cancel six weeks in advance, eight weeks in advance, you get the money back minus 10 % for their administrative tasks and such, what have you. But we always recommend travel insurance. And we're going to link you up to that in the show notes as well.
So speaking of extending your trip in Maine, I would say you're missing a huge part of the joy of the area that you're in if you don't extend your trip.
Dan (25:35)
100%. And we talked about earlier renting a car and having that flexibility just to drive up and down the coast and exploring inland Maine also. Maine has a lot of diverse areas and there's just so much to explore there and I think it would be a huge miss if you went in, just did the cruise and then left.
Mikkel (25:57)
Yeah, we did a seven-day driving itinerary after our cruise. We did a road trip. We ended in Portland, Maine, and I believe we started in Bar Harbor, where Acadia National Park is. We went to Boothbay Harbor, where there's a gorgeous botanical garden. That was a highlight. And of course, we wanted to eat more lobster after the incredible lobster we had on the ship.
Dan (26:21)
It would be truly rude not to go to Maine and eat lobster.
Mikkel (26:25)
Right, right.
Dan (26:26)
That didn't make sense.
Mikkel (26:26)
It would be rude to be in Maine and not support the fishermen that are farming the lobster. The lobster people. Also, when we were in Bar Harbor, and I think now that I say this, this is worth doing a separate episode about extending your time in Maine. When we were in Bar Harbor, one of the most memorable excursions I've ever done that we booked on our own, of course this wasn't during the Maine Windjammer trip,
Dan (26:33)
lobster people, I think we called them.
Mikkel (26:53)
was Lulu’s Lobster Boat, and learning about all of the lobster buoys and the colors of the buoys and how you get a lobster license and the generations and kind of the challenges that they face. It really, truly makes you appreciate what they are farming to feed people and to sell and to support their lives economically and the state. So yeah, that was all part of our own extension of our trip in Maine. So 10 out of 10.
Dan (26:58)
Mm-hmm.
Mikkel (27:22)
I will also link in the show notes to our seven-day road trip itinerary.
Dan (27:28)
So, two episodes on Maine Windjammer. You are now experts. You know everything we know. if...so, we truly encourage you to check out Maine Windjammer. Look at all the different itineraries, everything. And it's such a unique way to experience Maine and really experience history.
Mikkel (27:52)
Yeah, I love that and if you have any questions, sincerely, this is any time with us. But if you have any questions about the topic at hand, Maine Windjammer, and you want to know if it'll be a good fit for you or not, or maybe it's a question, like you are going soon and should you pack this over that, please reach out to us. We love hearing from you.
Please share this with a friend as we mentioned before, share it with a family member. That is what helps to keep us growing and excited and enthusiastic about sharing our passion for small ship cruising. until next time, keep sailing.
Dan (28:28)
Keep sailing.
