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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!

Portland Head Light is visible in the distance behind Nautilus, which is sailing in the foreground of this drone image.




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

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

$80 per Person | $450 Private Charter

Hop on one of our 2-hour morning or afternoon sails 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.

A photograph of a sunset viewed from the bow of Nautilus, looking back towards the stern. The sunset is just beginning to touch the ocean in the distance.


6:00 - 8:00 PM | Sunset Sail

Fall Hours May Vary

$95 per Person | $550 Private Charter

Sunset sails depart each evening for 2 hours 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.


Starting at $450 | Call for a Quote

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!


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


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.

With a large cockpit and wide cabin tops, you'll find plenty of comfortable seating options for all. Guests are free to move up to the bow for a great view while we're underway. 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 (bathroom) 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 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.

Nautilus is sailing in the early evening as the sky just begins to transition to sunset colours. Two women are sitting in the bow and are holding up their glasses in celebration.
  • What is the maximum passenger capacity?
    Nautilus's passenger capacity is 6 people maximum. This is determined by the U.S. Coast Guard so it is not flexible.
  • Do infants count towards passenger capacity?
    Yes. The passenger limit is based on the number of human lives aboard, rather than by seating room.
  • Do you take same-day bookings?
    YES we do! Our booking software with FareHarbor allows for same-day bookings. If a sail during a time slot you are interested in appears to be greyed out, you can give us a call to see if there are any seats remaining. One important thing to note: if the crew are not currently on the boat, it will take us roughly one hour to arrive at the boat and complete an all-systems safety check, so please call as far in advance as possible.
  • Will we tip (heel) over?
    As a sailboat, the Nautilus is designed to lean to one side or the other with the pressure of the wind in her sails, with the extent of that heeling depending on the strength of the wind. If you’d like a more spirited sail, we recommend checking the forecast for winds of 13 knots (roughly 15 miles per hour) or higher. Morning and Sunset Sails tend to be the calmest, while Afternoon Sails are generally more lively. In Portland we usually receive the strongest winds in May, June, September, and October, while July and August are the calmest months.
  • Is there a bathroom on board?
    Yes! We have a marine toilet, also called a head. The marina also has facilities for all guests in the form of 3 single-stall restrooms.
  • Are life jackets required to be worn?
    Due to Federal law, anyone under 13 years of age is required to wear a life jacket on board any commercial vessel that is off the dock. Adults can choose to wear one if it would make them feel comfortable, but it is not required.
  • What is your general cancellation policy?
    Please cancel one week in advance of your sail to receive a full refund. Cancellations made with under one week’s notice will not receive a refund unless they are due solely to sudden illness (see covid-19 policy below).
  • What happens if it rains?
    In the event of poor weather or unsafe conditions determined by the Captain at the time of the sail, a full refund will be issued.
  • Do you have a covid-19 / illness refund policy?
    If you become sick with covid-19, the flu, or any other contagious illness and need to cancel, you will receive a full refund. We appreciate your help in not spreading any illnesses to the crew!
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