10 Reasons to Sail on the Grace Bailey, a Historic Maine Windjammer

I’ve sailed on Maine Windjammer’s ten times, and if someone asked me which vacation I keep coming back to, this would be it. There’s something magical about spending a few days aboard the Grace Bailey Schooner, a beautifully restored schooner that has been sailing the Maine coast since 1882.

Whether you’re looking to unplug, enjoy incredible food or simply experience the beauty of Penobscot Bay from the water, here are my 10 favorite reasons to sail aboard the Grace Bailey.

1. The sailing itself

This is the biggest reason to go. If you love feeling the wind in your hair while an experienced captain and crew expertly handle the sails, then a Maine windjammer vacation is for you.

On our first day, we sailed nearly 40 miles from Rockland, passing North Haven Island, Stonington, Jericho Bay and Southwest Harbor before dropping anchor in peaceful Allen Cove. We spent about seven glorious hours under sail, watching Maine’s rugged coastline drift by.

2. Step back in time

Sailing aboard the Grace Bailey feels like traveling back to the late 1800s. This authentic schooner offers a glimpse into life aboard a traditional tall ship without sacrificing comfort.

One of the passengers on our trip had an especially meaningful connection to the boat. He first joined the Grace Bailey as a 15-year-old crew member in 1952 and has returned nearly every year since.

It’s also the perfect place to disconnect. There are no televisions, no constant news updates and very little reason to look at your phone. While there is cell service in parts of Penobscot Bay, most guests happily leave the modern world behind for a few days.

3. The incredible food

One of the best parts of sailing on the Grace Bailey is that you don’t have to cook—or even think about cooking.

Chef Ian somehow creates restaurant-quality meals from the schooner’s tiny galley. During our trip we enjoyed dishes like lemon salmon, chicken pot pie, black bean salad, prime rib with duck-fat roasted potatoes and jicama slaw.

Each evening, sous chef Hailey prepared beautiful charcuterie boards along with smoked trout dip, spring rolls and other appetizers.

Breakfasts included French toast, blueberry pancakes with homemade blueberry compote and maple syrup, plus eggs cooked to order.

Then there’s the traditional Maine lobster bake, which alone is worth the trip. We feasted on steamed lobster, fresh corn on the cob, watermelon, tri-color farfalle pasta salad, Cape Cod potato chips and homemade sangria. Even the bread is baked fresh onboard.

4. The people you meet

One thing I’ve learned after ten windjammer trips is that they attract genuinely interesting, friendly people.

Everyone comes for the same reason: to relax, enjoy nature and experience something different. Conversations happen naturally, whether you’re sitting on deck, reading beneath the awning or sharing stories after dinner.

By the end of the trip, strangers often feel like old friends.

5. Maine’s unspoiled beauty

There’s no better way to experience the Maine coast than from the deck of a schooner.

We sailed past quiet islands, rocky shorelines and picturesque lighthouses while seeing very little boat traffic. Curious seals popped their heads above the water to inspect us, while ospreys, bald eagles, loons and porpoises made regular appearances. Some guests have even spotted whales on previous trips.

We also had opportunities to swim from the boat while anchored near Islesboro and Babson Island in the cool, refreshing waters of Penobscot Bay.

6. Visit places most travelers never see

One of the biggest advantages of traveling by windjammer is visiting places that are difficult—or sometimes impossible—to reach by car.

We explored the charming fishing village of Stonington and visited uninhabited nature preserves, including Babson Island. We also stopped in Buck’s Harbor, once home to beloved children’s author Robert McCloskey, who wrote Make Way for Ducklings.

Since we visited on a Wednesday, we enjoyed the local farmers market, where vendors sold everything from lavender and candles to vegetables and the most unusual mushrooms I’d ever seen.

7. Evenings filled with music

Many Maine windjammers have musical captains or guests, and passengers are encouraged to bring instruments.

During our sailing, Maine musician Paddy Mills joined us onboard. His specialty is traditional sea songs and maritime folk music, many of which he wrote himself.

Listening to Paddy play guitar beneath the awning by the glow of kerosene lanterns while sipping a glass of wine or a local beer was one of those travel moments I’ll never forget.

8. The night sky

One of my favorite memories came after everyone else had gone to bed.

We happened to visit during a new moon, so I convinced Cam to climb up on deck with me. Without city lights, the sky exploded with stars—more than I could possibly count.

The only other time I’ve experienced a night sky this spectacular was while watching Halley’s Comet from the Australian Outback years ago.

9. An outstanding captain and crew

Captain Tripp Seaman (yes, that’s really his name!) and his crew made the entire trip feel effortless.

First Mate Maya, Jules, Bridget and Marissa handled everything from raising sails to helping guests ashore, always with smiles and endless energy. Chef Ian and messmate Hailey also pitched in whenever an extra set of hands was needed.

Their professionalism, enthusiasm and teamwork helped make this one of my favorite windjammer trips yet.

10. Rockland is worth exploring, too

Don’t rush home after your sailing adventure.

Rockland has an excellent restaurant and art scene that’s worth an extra day or two. Before boarding, we browsed local galleries, enjoyed oysters at Primo and had dinner at North Beacon Oyster House.

On your drive home, make one final stop at McLoon’s Lobster Shack (photo above) in nearby South Thomaston for what I think is one of the best lobster rolls in Maine.

Final thoughts

I’ve traveled all over the world, but I continue returning to Maine and the Grace Bailey. There’s something special about slowing down, letting the wind determine your pace and spending a few days surrounded by great food, wonderful people and some of the most beautiful scenery in New England.

If you’ve ever dreamed of unplugging, sailing aboard a historic schooner and experiencing the Maine coast the way it was meant to be seen, a trip on the Grace Bailey belongs on your travel bucket list.