Sail250: New York City and Boston in 2026
We’re excited to announce that after 40 years the Schooner American Eagle will be making her return to New York City as part of the Sail4th celebration over July 4th weekend to celebrate the 250th anniversary of the founding of the United States.
After New York we will be making our way up to Boston and join the Sail Boston festivities the next weekend.
What is Sail250?
Sail250 is a multi-state event to celebrate the 250th anniversary of the founding of the United States. Many of the largest tall ships in the world will be in attendance representing countries from all over the globe.
Fleet event will be taking place in five East coast cities: New Orleans, Norfolk, Baltimore, New York City, and Boston. We plan on attending Sail4th taking place in New York City over the Fourth of July weekend, and Sail Boston the next weekend.
Due to the length of the journey we will be splitting the trip into two legs; the first will be sailing from Rockland to Sail 4th in New York City and the second will be attending Sail Boston and returning to Rockland.
You are more than welcome to join us for both legs of our Sail250 trip in 2026!
Sail4th Itinerary
Our trip will board on Sunday, June 28th at the North End Shipyard in Rockland. Boarding will be a bit earlier in the day, as we will be departing that evening to get a head start on our long journey south.
From Rockland we’ll sail south, stopping first in Casco Bay outside of Portland. The next day will be spent heading down to Massachusetts Bay and close to the Cape Cod Canal. After passing through the canal we’ll spend a nights in Rhode Island and Long Island Sound before heading through Hell’s Gate and down the East River, arriving in New York Harbor on July 3rd.
You’ll have time to both walk around New York City and watch the incredible parade of sail from the procession itself aboard the American Eagle. Here’s a list of many of the tall ships that will be joining the event.
After Sail4th we’ll make our way up to our second home of Gloucester, Massachusetts where any guest not joining us for the whole trip can disembark. If anyone wants to return to Rockland to pick up their vehicle we will be arranging transportation. Gloucester is also a short commuter rail ride from Boston’s Logan Airport and their many transportation options.
Anyone remaining with us for the second leg of our Sail250 trip will spend a night at a hotel in Gloucester, giving the crew time to turn around the boat for the next trip.
Sail Boston Itinerary
Guests joining us for Sail Boston can either meet the schooner in Gloucester or be picked up in Rockland and brought down to Gloucester to board on Friday, July 10th.
From Gloucester we’ll sail straight to Boston to join the festivities, complete with Parade of Sail and opportunities to explore Boston and tall ships from the North and South American, Europe, and Asia. Here’s a list of some of the larger vessels that will be attending Sail Boston.
Leaving Boston we’ll take our time heading back to Rockland, first making a stop on Cape Cod with time to walk around on land. The next day we’ll begin our trip back to Rockland, returning to our home at the North End Shipyard late in the morning on Sunday, July 19th.
Both the Sail Boston and Sail4th trips will be quite special events, with attendance not seen since United States Bicentennial in 1976. We hope to see you on board or at the festivities!
Booking Sail4th and Sail Boston Trips and Trip Cost
Due to the unique nature of the Sail4th and Sail Boston trips, we will only be taking bookings over the phone for trips. If you would like to begin and end your trip in Rockland, you are welcome to do so. We will be providing transportation (at a small cost) to help bring people back to Rockland after Sail4th or to Gloucester before Sail Boston.
The trips will be capped at 24 guests to ensure a bit more space on these long trips. We will still have two singles available, as always.
The 11-night Sail4th trip from Rockland to New York ending in Gloucester will be priced as follows:
$3,218 per person cost
$6,436 per cabin, double or upper/lower
$3,878 for single cabins
The 9-night Sail Boston trip from Gloucester to Boston ending in Rockland will be priced as follows:
$2,822 per person cost
$5,644 per cabin, double or upper/lower
$3,362 for single cabins