InDepthNH.org’s senior writer Paula Tracy, above, took the photos below and this selfie.
By PAULA TRACY, InDepthNH.org
ROCKLAND, MAINE – Midcoast Maine’s magnificent water, with its more than 700 islands, was opened up to me on a three-day windjammer cruise in September marking my favorite adventure in 2025.
Looking back through my phone at pictures from the year – which I suggest is a good way to look at 2025 today – the experience I had aboard the historic Grace Bailey stands out as the best adventure I had last year.
The Grace Bailey is among the fleet of these 1800s wooden vessels that were once the tractor trailers of the seas in their day before rail. Re-outfitted to allow about 20 to cruise for days, this can be your moving home, exploring for three- or seven-day trips.
The Grace Bailey is pictured above.
Anchored in Camden and Rockland, Maine, it cost me $1,300 for three days, including lodging, food excluding tips for the crew of six.
I was invited to help hoist sails and cruise aboard a vessel that quietly revealed a stunning landscape fewer than 100 miles from my home in Center Harbor and a place few can see if they don’t have a boat of their own to get there.
There was no itinerary other than trying to find good wind and being a day’s sail or so back to Rockland. Captain Sam Sikkema noted that they never stop at the same island twice each season.
A lobster bake on shore
We went from Rockland Harbor, through the Fox Island Thoroughfare as far out as a night anchor off the remote back side of Isle au Haut.
Seven-day sails go farther afield. There are themed sails and special trips listed on the website. It seems crazy that we live so close but it is hard to explore these places mentioned through the Maine Island Trail Association https://mita.org/.
Most come to them by private vessel including a sea kayak, which I don’t have nor do I know anyone who is up for that sort of more perilous adventure.
Above, Paula Tracy helps hoist sails.
The Grace Bailey is a handsome nationally registered historic vessel that cuts through the water with surprisingly great speed given her wide beam. She travels by wind with no noise except the sound of waves lapping against the vessel against her wooden hull. Once used to haul pineapples quickly to market in more southern waters, she has been re-appointed to take passengers but this is by no means a typical cruise.
She can be moving at close to 20 miles per hour. In harbor or without wind, there is a separate boat with an engine that pushes the Grace Bailey, but the boat herself has no power, other than the wind caught in the sails.
The fleet moves among the beautiful rocky islands with the mainland in the distance where the water even in September is in the chilly range.
My memories are full of glistening water, the sounds of all sorts of water and shore birds, wildlife spotted by binoculars, moving fast past lighthouses, and starlight nights where you walk about the deck by lantern in a quiet cove.
I twice explored these islands in my earlier life aboard small motor boats.
The first was in the late 1980s during my college years while visiting friends near Hurricane Island. Then in about 1995, during my early parenting years, in Vinalhaven where we shared a rental with another family who had a boat.
I wanted to go back to see this beautiful area after many happy summer days and learned about the windjammers as a possible option.
For those of us who travel solo but are not used to it, this was an opportunity to be alone while also connecting with and meeting about 20 other passengers from all over.
Many were couples celebrating special events who were from New England and they were all very nice. I did not feel awkward that I was alone. I could find time to contemplate and just chill while also talking and sharing sights through the binoculars with the other passengers.
Above, discovering new friends and new shores.
On these cold days it is fun to look back at these pictures.
This trip was a welcome disconnect from the internet and the noise of life. To breathe. While we sometimes had cell service it was more the exception than the rule.
The sleeping accommodations were tiny but clean, white and comfortable. I was thankful I brought a sleeping bag as suggested. I got the best sleep of the year, as well, as we bobbed up and down.
There is a shared head in both cabin areas and a single shower. The food was amazing and the chef accommodated all tastes and diets.
Above, Floating home away from home.
Dining on deck
The chef was even willing to create a special curry sauce I like to dip my lobster in which he brought with provisions for our island lobster bake the second day on Brimstone Island.
I last visited this volcanic island in 1997. It has amazing shiny black stones for a beach where we got off to explore its highlands and wildlife and I got a few shots of the boat at anchor.
Another highlight of the trip was meeting the ship’s cat, Fiji, above, who entertained us. She is the captain’s cat. Captain Sam Sikkema was friendly, professional and capable. And I plan to go again in 2026. To explore more about having a similar adventure in 2026, visit www.mainewindjammerfleet.com or https://www.sailgracebailey.com/
I am so thankful for the beauty of the coast of Maine, and the vessel that revealed it to me. There was peace I found, great memories recalled, and new friends I made aboard.
I wish InDepthNH.org readers great adventures, smooth sailing and a healthy and Happy New Year for outdoor fun, which I look forward to in 2026.