Daily Trips

Here at Sail Portland Maine, every day we provide two-hour public or private sails that might 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/$350 Private Charter
  • 1:30 PM – 3:30 PM     $65 per Person/$350 Private Charter
  • 6:00 PM – 8:00 PM (Fall hours vary) $80 per Person/$450 Private Charter

Saturday Sunsets Rosé

Sail Portland Maine favorite!! Join us for Portland Maine sailing trips every Saturday evening to enjoy our unique rosé sail. We will be featuring a delicious rosé, and local charcuterie boxes, 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.

Private Charters

A great way to enjoy the bay if you have a party of six, a family, or even if you are 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 $150/hour which will allow you to extend the fun.

Come sail with us!