Sailing daily from Fore Points Marina beginning May 5, 2023!

Nautilus Sailing Company

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!

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10:30 AM - 12:30 PM | Morning Sail

1:30 PM - 3:30 PM | Afternoon Sail

$80 per Person | $450 Private Charter

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

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.

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6:00 - 8:00 PM | Sunset Sail

Fall Hours May Vary

$95 per Person | $550 Private Charter

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.

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Starting at $450 |  Call for a Quote

From intimate wedding ceremonies, to memorable anniversary celebrations, to unique bachelor and bachelorette parties, to corporate outings, our 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!


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

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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.

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.

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 porpoise and seals. With Captain Nick or Captain Sam  as your seasoned guide, sit back and enjoy the view while you learn about our treasured Maine coast.

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    The best Sunset Cruises in Portland according to Viator travelers are: Private Sunset Charter on a Vintage Lobster Boat; Downtown Portland, Maine City and Lighthouse Tour-2.5 hour Land Tour; Portland Tall Ship Cruise on Casco Bay; Private Lighthouse Sightseeing Charter on a Vintage Lobster Boat; Vintage Fire Truck Sightseeing Tour of Portland Maine

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    Lighthouse Cruise. Join us for 1 1/2 hours as we cruise along the rugged coastline, complete with lighthouses, seals, seabirds, and historic forts. Pack a meal, bring your favorite wine or beer and sit back and relax as you slip through the tranquil waters of Casco Bay. All ages are welcome!

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