This summer, I had the chance to try a few different sails around Maine, and I have to say, sunset sailing is my absolute favorite.

What makes a sunset sail with Portland Schooner Company stand out is that it’s BYOB.

You can bring your favorite bottle of wine, some snacks, and anything else you need for a perfect two-hour journey around Casco Bay.

Here’s a look into my experience out on the water!

Sunset Sail with Portland Schooner Co.

At Portland Schooner Company, the love of the sea is at the heart of everything they do.

Their fleet of handcrafted wooden vessels proudly represents Maine’s rich shipbuilding heritage.

With each schooner being a living piece of history.

These historic ships still sail the waters of Casco Bay just as they have for generations, offering passengers an authentic glimpse into the state’s maritime past.

From May through October, you can step aboard for a public sail or even reserve a private charter.

Whether it’s the morning light on the bay or the glow of the setting sun, every trip is designed to share the passion for sailing with guests.

Onboard the Ocean Gateway Sunset Sail

I booked a sunset sail with Portland Schooner Company that departed from the Ocean Gateway Pier.

Just a heads up, this is not the same pier as the Casco Bay Ferry, so make sure you go to the right spot.

We arrived about 15 minutes early at 4:45 PM, checked in at the small booth, and picked up my ticket.

The crew told us which boat we’d be on, and once it was time, we walked down the dock to board.

As soon as everyone settled in, the sails were pulled up with help from passengers on board, which made the whole experience feel hands-on.

Then, the schooner gently set off into Casco Bay.

Since I went in mid-September, it was chilly once we were out on the water, so definitely bring a coat if you’re planning a fall sail.

If you are looking for a more affordable option, this $14 Portland Maine Sunset Cruise Is the Best Deal in Town!

BYOB on the Water

My favorite part of this cruise was that it’s BYOB, which means you can truly bring whatever you’d like to sip and snack on.

Some people had a bottle of wine for a date night, others popped open champagne for a celebration, and a few even came prepared with small coolers full of snacks and drinks.

It felt like having a true picnic out on the sea.

With the cruise lasting about two hours, there’s plenty of time to sip, relax, and enjoy the views while the boat glides through the bay.

If you want a cruise with a guided wine tasting, You Have to Try This Oyster and Wine Sail in Portland, Maine!

Sunset Views on the Schooner

Our sail started under cloudy skies, but just as the sun began to set, the clouds broke apart.

Suddenly, the whole horizon lit up in golden hues that shimmered across the water.

It was one of the prettiest sunsets I’ve seen in Maine all summer.

From the schooner, we watched the sun drop behind Portland, Peaks Island, and the old forts scattered in the bay.

We even spotted a curious seal bobbing its head as if it wanted to join in on the view.

By the time we pulled back into the pier, the golden glow had shifted into soft pinks, which felt like the perfect ending to the evening.

Book Your Sail with Portland Schooner Company

Portland Schooner Company offers so many different sails throughout the season, from daytime lighthouse trips to laid-back sunset journeys like mine.

You can book your sunset sail here.

If you’re looking for a relaxed cruise that moves at your own pace, this is the company I recommend.

They even offer seasonal specialty sails, like their Fall Donut and Cider Cruise, which sounds like the best way to experience Casco Bay.

And if you are visiting in fall, make sure to read my Ultimate Guide to Maine’s Fall Foliage: When and Where to Go!

Whether you’re visiting Portland for the first time or you’re a local looking for a new way to enjoy the water, there’s a sail for everyone.

Explore More of Maine

I love sailing on the water in Maine, whether it’s the heart of summer or the crisp air of fall.

If you are looking for a more affordable option, This $14 Portland Maine Sunset Cruise Is the Best Deal in Town.

Or, for a unique experience, You Have to Try This Oyster and Wine Sail in Portland, Maine.

Make sure to try one of these 21 Best Lobster Rolls in Maine: From A Local! (2025).