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A close-up image of a block and pulley on the main sail, with the waterfront of Portland visible behind it at twilight.
a small circular logo for Nautilus Sailing Company, depicting the boat in dark green riding atop some waves.

Relax and enjoy the best views of Portland aboard Nautilus

Grab your favorite bottle of wine and step aboard for an experience you'll always remember. Sail past lighthouses, the historic Fort Gorges, and learn about the rich history of Portland Harbor from our seasoned and passionate crew.

Sail Casco Bay with Us

Book a sailing adventure for a day trip, sunset cruise or your own private charter in Portland, Maine!

a group of people in their mid-20s are shown talking in the cockpit of the boat. One is alone sitting midships.

DAY SAILS

 

11:00 AM - 1:00 PM | Morning Sail

3:00 PM - 5:00 PM | Afternoon Sail


$80 per Person | $450 Private Charter

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Public sails depart daily to explore Maine’s diverse and scenic Portland Harbor.

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Choose our first trip for a calm morning outing, or join us in the afternoon when the wind picks up. Get on the water with Nautilus Sailing Company for a uniquely memorable Portland, Maine excursion.

image looking forward at the bow of a sailboat and the dark blue water beyond, the jib is filled with wind.

SUNSET SAILS

 

6:00 - 8:00 PM | Sunset Sail

Fall Hours May Vary


$95 per Person | $550 Private Charter

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Public sunset sails depart each evening to enjoy golden hour views of Maine’s diverse and scenic Portland Harbor.

 

Bring your camera and favorite cocktail and get on the water with Nautilus Sailing Company to enjoy the best sunset views of Portland, Maine.

a tray of charcuterie rests on the forward hatch of a sailboat, near some coiled rope and the main mast.

CUSTOM CHARTERS

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Starting at $450 | Call for a Quote

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Need an extra hour or some additional flexibility? From intimate wedding ceremonies, to memorable anniversary celebrations, to unique bachelor and bachelorette parties, to corporate outings, our custom private charters are fully customizable to meet your needs.

 

Call to plan your ideal Portland Harbor sail charter and make your next special event epic!

BOOKING CALENDAR

Have a date in mind? View our Booking Calendar below:

ABOUT US

Spring Point Lighthouse is shown in the background, in the foreground a group of people looking at the lighthouse.

Designed and built to look and feel like the sailing vessels of days gone by, our 37' ketch Nautilus perfectly combines traditional form and modern function.

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With a large cockpit and wide cabin tops, you'll find plenty of comfortable seating options for all. The spacious cabin offers ample space for lounging, eating, or a brief respite from the elements. The galley has all the amenities of home, including an ice box and stove, and there is also a large head with push button facilities-- everything you need to create your ideal Portland excursion.

Join us! We're certain you'll be glad you did.

Step aboard the sailboat Nautilus and experience the real magic of Casco Bay.

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Relax and unwind as we silence the motor and let the wind take us sailing past lighthouses, between the islands, past historic forts, and even alongside playful porpoises and seals. With Captain Sam and first mate Crow as your seasoned guides, sit back and enjoy the view while you learn about our treasured Maine coast.

Two people flake (fold) the main sail of Nautilus in preparation to return to the dock.
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