Daily Trips

Each day, we provide two-hour public sails that will have you sailing past lighthouses, historic forts, and seals swimming in the harbor of Casco Bay. At Sail Portland Maine we offer intimate, crowd-free, professionally-captained sailing excursions aboard our vessel, the Eleanor Hawkes.

We provide multiple trip options for you to enjoy your time on the water here in Portland, Maine. You can choose from three different sailing times throughout the day:

  • 10:30 AM – 12:30 PM $65 per Person
  • 1:30 PM – 3:30 PM     $65 per Person
  • 6:00 PM – 8:00 PM (Fall hours vary) $80 per Person

Saturday Sunsets Roséportland maine sailing

Join us for Portland Maine sailing trips every Saturday evening to enjoy our unique rosé sail. We will be featuring a delicious rosé, allowing you to enjoy all that Maine has to offer while taking in the magnificent sunsets on Casco Bay. These trips are $99 per person.


Craft Beer (Thursdays through September)

Experience the same type of sail as above, but rather than rosé we will be serving up tasty craft beers from local breweries. These trips are $99 per person.

Private Charters

If you have a party of six, a family, or even just a couple who wants the opportunity to have the boat to yourselves, a private charter is always an option, based on availability.

Private charters could be anything from a couple wanting to sail to one of the nearby island restaurants for an anniversary dinner and then a cruise back under the stars, or a couple who wants to elope and get married by the captain with a few friends to witness – your imagination is the limit! Catering is available as well.

The rate for a private two-hour charter is $350/$450 day/sunset. Each additional hour is $100/hour which will allow you to extend the fun.

Come sail with us!