Overnight Cruise on Grace Bailey Maine Windjammer Sailboat for a Relaxing Slow Travel Vacation
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Overnight Cruise on Grace Bailey Maine Windjammer Sailboat for a Relaxing Slow Travel Vacation
Bonus: NYC Sail4th 250, Once-in-a-Lifetime Flotilla featuring Two Historic Maine Windjammer Cruise Ships
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πΊπΈ America turns 250 this July 4th, and New York Harbor is throwing the biggest nautical celebration in a generation. We're breaking down everything you need to know about Sail4th 250 β the historic Parade of Sails for the USA's semiquincentennial, happening on July Fourth in the Hudson River next to Manhattan, including events from July 3rd to 6th, 2026.
We sat down with William Armstrong, Communications Director for Sail4th 250, and Captain Tyler of American Eagle β one of two Maine Windjammer schooners sailing in the Parade alongside Angelique.
We cover what makes this event so rare, how 5 years of international coordination made it happen, and why a ship from India is sailing over 12,000 miles just to be there.
Whether you're heading to New York in person or watching on NBC, we've got you covered: where to watch from shore, how to bring your own boat into the harbor, which ships to look for, and how to track every tall ship in real time using the Aqua Map app.
We also share what it means to us personally, including why Mikkel has been dreaming about this moment since childhood, as she looks at a 1976 flotilla poster on her parents' wall.
π¦ Find out what it's like to sail on American Eagle:
- Part 1: Sailing Cruises on Historic Maine Windjammer Ships: https://sometimessailing.com/gczo
- Part 2: Maine Island Hopping on a Windjammer Sailing Cruise: https://sometimessailing.com/8xhm
- Maine Windjammer firsthand accounts, our website, with photos: https://sometimessailing.com/category/cruise-lines/maine-windjammer/
π Links mentioned in this episode:
- Sail4th 250 event https://sail4th.org/ & the Tall Ships "encyclopedia" https://sail4th.org/tall-ships
- Aqua Map app for iPhone - https://apps.apple.com/us/app/aqua-map-boating/id919552329 β or Android β https://play.google.com/store/apps/details?id=com.gec.MarineApp.WorldViewerLite&hl=en_US
πΊπΈ Subscribe and follow! We'll be back after July 4th with a live recap episode.
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Need help planning your trip? Check out our RESOURCES, whether you're looking to understand what cruise to book, which travel insurance is best, or how to organize your luggage with our packing lists: https://sometimessailing.com/resources/
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π SometimesSailing.com has even more planning tips, firsthand experiences, & advice.
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Β©2026 Small Ship Cruise Talk. All rights reserved. May contain affiliate links. Some trips and experiences have been hosted. As Amazon Associates, we earn from qualifying purchases. All opinions are our own.
Mikkel (00:35)
I am so excited for today's bonus episode. We are bringing you news of a very, very special event that is happening July 4th, 2026, in the harbor of New York City
Mikkel (00:49)
to commemorate the semi-quincentennial of the United States of America. That is its 250th anniversary or birthday, depending how you look at it. And it is such a special occasion happening in New York City, it's been coined Sail4th 250.
Mikkel (01:08)
And the reason we are talking about this on Small Ship Cruise Talk is because we have two episodes about a ship that will be
in the Parade of Sails. But our historic Maine Windjammer ships episode Part 1 and Part 2 that are linked in the show notes tells you exactly about the experience of being on a Maine Windjammer schooner, particularly in this case, American Eagle ship. And she will be sailing in Sail4th 250 in New York City.
Dan (01:43)
As most of you know the United States is celebrating their 250th anniversary this year. In addition to that, they're celebrating fourth of July and what better place to do it than New York City? Now to really these major events they're bringing in countless numbers of ships from all over the globe. These are not regular ships. They're historic sailing ships with the tall masts and the sails are gonna be out on display. It's gonna be quite picturesque.
Mikkel (02:14)
One hundred percent. I mean, even just looking online and in the app we're gonna share just is like, my jaw dropped in awe. I think of a peacock lifting all of his feathers, you know, and all of these ships, they're all gonna have their sails up just to display the grandeur of these incredible historical nautical vessels.
So the event is from July 3rd to 7th in the port of New York and New Jersey, but that's basically to say the Hudson River, which is the West Side River that borders the island of Manhattan, what most people think of when they think of New York City. And then the East River is a part of it on other days. So not particularly July 4th, but there is a schedule of events that we've linked in the show notes.
And we were able to talk to two very important people part of this event. So one of them was William Armstrong, who is the communications director for New York City's Sail 4th 250. And then the other was Captain Tyler, who is the captain of American Eagle, which is the ship that we had the honor and pleasure of sailing on a few years ago. And you can too, because it is a ship that is available to cruisers, and it is quite the incredible experience.
So again, those two episodes about our experience on American Eagle are linked in the show notes. And if you really want to put yourself on the ship so this monumentous event in New York City has more meaning to you, then I encourage you to listen to it. They are just chock full of amazing information.
One of the reasons this is really important to me to be at is not only because I am from Long Island, right by New York City, but because my parents have always had an illustrated poster of the 1976 historic flotilla in New York City. And to this day, even though they have moved to different houses, they have that poster hanging in their home. So when I heard that it was
happening, this Sail4th 250 in New York City, and I had this poster in my head, I thought, "Oh my gosh, I have to go. It is a once-in-a-generation event." And Dan, you are gonna do your diligence. And you are gonna watch from home. So we are covering this event from both angles. And that is why we are bringing you this bonus episode. We are gonna tell you how to watch from home.
We are gonna tell you what you need to know to watch in person, whether you are on land or you're gonna bring your boat there β and you can bring your boat there β and you're gonna have everything you need to be prepared to celebrate July 4th to the max.
So be sure to subscribe and follow us because we are gonna publish another bonus episode after July 4th, kind of as a little recording of history so we can recount what we saw and everything that was unique and exciting about the event.
Dan (05:22)
So we've talked about the American Eagle a few times. Now let's talk about its role in the flotilla. American Eagle and Angelique, another ship in the Maine Windjammer schooners collection, are two American vessels that will be sailing in the Parade on July Fourth.
Mikkel (05:37)
And the Parade of Sails is a two-hour event that is gonna have all these historic ships coming from all over the world. One of them is a ship coming from India that is sailing the furthest. It is sailing over 12,000 miles to be in this Parade.
And just as a little side note, but an important one, William Armstrong, the director of communications for the event, he goes by Bill, had shared that it took five years to coordinate the schedules of these ships. In one instance, he even told us that they had to ask a ship to change its own country's celebration so it could participate in the Parade of Sails. And Bill said that American Eagle and Angelique, the two Maine Windjammer schooners that are participating, really augment the whole Parade of Sails in a really big way. And when you see these ships, you will understand why. So the spectacle's part of it and makes the event extraordinary. Colombia, the country of Colombia, for example, their 212-foot three-masted ship, named Gloria, is going to sail in front of American Eagle.
Dan (06:48)
So what's interesting is the American Eagle was last in New York Harbor in 1986 for the Statue of Liberty and she hasn't been back since. So this will be almost like a little bit of a New York City homecoming for her 53 years later.
Mikkel (07:05)
And when she was there for this centennial of the Statue of Liberty, it was right after she was rebuilt from commercial fishing to be converted to a charter sailing ship for passengers, like us, to go on cruises. She was originally a fishing boat in Gloucester β I hope I'm saying that correctly β Massachusetts.
Mikkel (07:28)
When we sailed on American Eagle just a few years ago, it was owned and captained by Captain John. He was the owner after its commercial fishing life. But now Captain Tyler owns it. So let's listen to a quote about what it means to Captain Tyler to personally carry American Eagle into the New York Harbor for Sail4th 250, knowing the history the ship carries and what Captain John built that he is continuing to build upon in the future.
Captain Tyler (08:02)
It means a lot. This boat has a history that's, you know, larger than all of us. And she represents not only what she is as a wonderful artifact and a, you know, a product of her time, but also, you know, the hundreds and hundreds of thousands of people she's impacted over her, you know, many different facets of her life.
The event in New York Harbor was her, one of her first major event as a passionate carrying vessel. It was a, you know, a kind of a large undertaking and it feels very poignant and very cool to kind of bring all of that back around 40 years on and still be doing a wonderful thing with a really cool boat.
Mikkel (08:41)
So again, the history, the living history that you're going to be able to see and you can experience if you are part of Maine Windjammer's overnight cruises. And again, anyone can be. We were, and we're actually going again next week on another ship, Grace Bailey. That brings up another interesting point about the two ships that are participating in the Parade of Sails, because only certain ships in the Maine Windjammer fleet can go out in the ocean like Angelique and American Eagle can.
Dan (09:14)
What's also gonna be really interesting is there's gonna be passengers on board both of those ships. So it's gonna be a legitimate cruise that people get to be a part of this flotilla.
Mikkel (09:25)
Right. So, along with those two special things, so the first one being American Eagle holds a rare, offshore license. So one of the things that makes this trip possible, it can go to the ocean and it can go from the top of Maine down to the New York Harbor, plus the passengers on it make it extra special.
And another thing on top of this is that the voyage from Rockland, Maine, where the ship boards β everybody embarks going on this journey on June 28th β it's gonna be 11 nights. Now that's really rare for a Maine Windjammer cruise. They've done seven, eight, nine nights. Sometimes you know they sell out right away, sometimes they don't. It depends on the itinerary. But we learned that this itinerary sold out immediately. So the demand was so high, there is a wait list to go on this cruise.
So, it's 11 nights total. The journey to New York is gonna take four to five days. So again, they leave on the 28th from Maine. They're gonna go south. They're gonna go Cod during daylight hours, which will be so special. And Captain Tyler shared that they are possibly going to stop in Port Jefferson on Long Island, which was really cool to me because I grew up going there to see my aunt and uncle and cousin who lived out there. And yes, it is a city on Long Island, out east on the water. So that was really cool to hear.
Dan (10:53)
In true Maine Windjammer fashion, they don't have a set schedule or ports of call, so all of it is subject to change but you know, they know they have to be in New York City for the 4th.
For this journey, they brought on a second captain that has experience in the Long Island Sound and the New York Harbor. So just to make sure they get it right and it goes off, you know, without a hitch.
Mikkel (11:16)
Yes, exactly.
The planned dock location, if you're curious to see American Eagle, if you're going in person, is Pier 26, and that's on the Lower West Side of Manhattan. Now they're not going to be doing public tours because they're going to have paying guests on board.
But the exciting thing is if you go to Sail4th 250 in person β and again it runs from July 3rd to July 6th β is that you are gonna be able to get on naval ships, and also passenger ships like this, β some of them, not American Eagle β for free. So it's gonna be completely complimentary. Just make sure you wear closed-toed shoes because that is one of the requirements to board these ships for safety purposes.
Dan (12:01)
That's a really good point. Like, the event itself goes multiple days, but it's only televised on July 4th. And that is on NBC from 7:00 am until
Eastern time.
Mikkel (12:15)
And you're gonna be watching from home, like we said, and I'm gonna be there in person. So if you don't want to deal with some of the craziness of summer in the city during this holiday time, which is interesting because a lot of people actually leave New York City who live there for holidays like this, they go out east to the Hamptons. I'm sure some people go upstate, some people go south to Maryland or the Chesapeake Bay, you know, DC area. You're gonna be watching from home.
So starting early in the morning is an incredible fly over. It's gonna have the famous Blue Angels, of course, and they are flying in β literally β some jets from the UK and the French Air Forces who are going to participate in this historic
aerial display before the main Parade of Sails. So that spectacle is gonna last approximately one hour. So if you want to see that, you're gonna want to make sure that you are stationed wherever you're watching from by might be pushing it. So you know the Parade of Sails begins at 9:30. So keep in mind that this flyover is before that.
Dan (13:35)
Right. Some of the other things that are happening is Secretary of the Navy will be on a platform ship out in the Hudson. The Queen Mary 2 will be anchored with guests on board.
Mikkel (13:45)
Yes, that's another great point because the Queen Mary 2 is a famous Cunard cruise ship. You can cruise on that as well. So I love that you made that point, Dan.
Dan (13:57)
And then also in the evening, Macy's will have a fireworks event, and that'll be visible throughout most of the city.
Mikkel (14:03)
And that is also televised every year on NBC. And that is incredible as well. One of the cool things is if you're a coin collector, you can get a commemorative coin online. It's the last one designed by Joel Iskowitz, who is a well-known numismatic artist. Now, I had to look this up. It's an artist specializing in coin design. He unfortunately passed away April 23rd of 2026, this year.
And you can get that in a variety of metals, copper, silver, and gold. The link is on the website for Sail4th 250. But one of the things I thought was really special is what the inscription reads. And that is: "The Port of New York and New Jersey and the USA welcome the Tall Ships of the World in Honor of America's Semiquincentennial."
Dan (14:56)
I had no idea that there was specialized⦠It goes on and on.
Mikkel (14:59)
All this fanfare? Well, now you know.
It doesn't stop, you know? Like, I can imagine all beer, the hot dogs, all the events. You know, you can watch this event in person. Let's talk about that a little. You can watch this event in person from a variety of locations throughout New York and New Jersey. Two of those places in New York are Battery Park,
or Governor's Island. Governor's Island, you need a ticket for. They are selling out quickly. The VIP packages are sold out already, but there's other general admission tickets that are $200 a piece because it includes food and access to Governor's Island for this.
But you can watch also from the Hoboken Waterfront, which I'm pretty sure that's where I'm gonna watch it from with some friends we have coming up from Charleston, because you're just gonna get that amazing view of the Manhattan skyline behind the ships on the Hudson River. So I think I'm gonna opt for that, even though Battery Park is really enticing because you'll be able to see the Statue of Liberty from there.
Dan (16:06)
If you are there in person, American Eagle and Angelique are planning to be docked at Pier 26 on the Lower West Side. So make sure you check them out. Angelique is easy to spot because she has red or almost rust colored sails.
Mikkel (16:23)
Yeah, and from the Tall Ships "encyclopedia," I would call it, on the website for the event, again, linked in the show notes. From what we can tell, most of the ships have like a white or off-white canvas for their sails. But Angelique is the only one with these rust-colored sails. There's another ship that has blue-colored sails. I think it's called Fog or Foggy, or something like that. But this is the only one with that color. So when you are scanning, even on NBC, if you're scanning what they are showing and you see red sails, she is Angelique. So that's really exciting.
You know, another cool way to look up the ships besides that encyclopedia, that I'm calling it, of Tall Ships on their website, is Aqua Map app. Now that is linked in our show notes as well.
And when you open it, it's almost like Cruise Mapper. If you've ever been on Cruise Mapper, you can see where all the ships, all the Tall Ships participating in Sail4th 250 in New York City, are right now. So, you know, when we looked, it was all up and down the east coast of the United States into Central America. So you could see all of the Americas. And you can also see one of the ships in California.
And I just think it's gonna be so cool on July third to see all of these ships converging to go to the island of Manhattan.
Dan (17:56)
It's almost worth it just to be in New York a day or two early just to see them all come in and kind of s wa watch all the activity.
Mikkel (18:03)
Yeah, yeah. I love that it's a multi-date event because I think a lot of people aren't gonna want to deal with the crowds going to New York on July 4th. So what a great reason to go on the 3rd, like you said, or even like Monday on the 6th. Just don't go the 7th, because the event is over.
Also, a lot of the ships might leave after July 4th. Like we were talking to Katharine, who works with American Eagle, and she was saying, they might leave the night of the 4th, they might leave the 5th. It really depends on what the weather is doing.
And that's another point: time they're gonna be docked there.
So I want to go back to what I mentioned that you can take your boat into the New York City harbor. This is important. If you are a boater, and you want to bring your boat into the harbor for July 4th, shockingly, you can. It's actually free to register your boat.
The Coast Guard is going to require all spectator vessels that have a permit that they applied for in advance β which you can do right now β to be anchored by 6:00 am on July 4th. And once the event begins, you cannot move. So you can't move until later that day when the Coast Guard clears everybody to leave. And just for anybody going at all, no drones are permitted in the area. Now, Dan, you've worked with somebody who had to fly a drone by the Brooklyn Bridge for other work purposes in the past. And that was so stringent, right? Like, so, normally, you can't.
Dan (19:27)
Much of Manhattan is restricted airspace for drones. So there's only on a good day, on a normal day, there's only very small windows that you can fly a drone. So this is no drones whatsoever for this event.
Mikkel (19:41)
Right, so leave the drone at home and just save yourself the heartache of, you know, being told that you cannot fly it.
This is gonna be an incredible event. We stood on American Eagle's deck. We helped raise her sails, especially Dan. They loved how tall you are. Dan is 6'2". They loved how tall he was to help hoist her sails. We ate lobster on board.
And on July 4th, she's sailing past the Statue of Liberty with her twenty-six passengers in front of millions of people, along with Angelique, two historic Maine Windjammer schooners for America's 250th birthday.
Dan (20:22)
You know, going to New York sounds amazing. However, I'm gonna be watching it on NBC and really gonna be looking forward to just pageantry, how they put the show together and I'll be able to see multiple different angles and a lot of other things that are happening in the city, and you'll be on the ground and seeing it live.
Mikkel (20:43)
I'm probably FaceTiming you at some point so you can see it. And you, listening, can bring yourself on that ship through our two podcast episodes about our American Eagle experience. And also if this is so exciting to you and you didn't know about Maine Windjammer ships in the past, then you can also dream about sailing on her one day. And if you are a visual person, you know, then I encourage you to click the link in our show notes.
Dan (20:46)
Right. Yeah.
Mikkel (21:13)
That is our full trip report, including photos of being on American Eagle. Also, if you know a friend that is super curious about the Sail 4th 250 events, we would love it if you hit that share button. It really helps us out to help spread the word about Small Ship Cruise Talk. Well, happy birthday to the United States. Happy cruising.
And we will speak to you after the Sail4th 250 event for our end-of-event report.
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