Every day we offer two-hour public or private charters that might have you cruising past lighthouses, historic forts, and seals swimming in the harbor of Casco Bay. At Sail Portland Maine we offer intimate, crowd-free, professionally-captained excursions aboard our vessels, the Eleanor Hawkes or the Calista Ann. 

We provide multiple trip options to ensure that your Portland, Maine boat cruise fits into your schedule. You can choose from three different charter times throughout the day:

Eleanor Hawkes (sailboat)

  • 10:30 AM – 12:30 PM: $75 per Person/$400 Private Charter
  • 1:30 PM – 3:30 PM: $75 per Person/$400 Private Charter
  • 6:00 PM – 8:00 PM (Fall hours vary): $90 per Person/$500 Private Charter

Calista Ann (cocktail cruiser)

  • 12:00 PM – 2:00 PM: $75 per Person
  • 3:00 PM – 5:00 PM: $75 per Person 
  • 6:00 PM – 8:00 PM (Fall hours vary): $90 per Person
  • All private charters on Calista Ann are sold by a per ticket basis (call for any questions)

Each additional hour is $200/hour which will allow you to extend the fun.

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 start at 2 hours minimum and can go as long as 8 hours!

If you have a group of people who really want to lay back, you will want to book the Calista Ann, she is a new addition to the company, and keeping with the style and intimacy that our brand represents. She is a classic Down East Picnic boat and is a comfortable cocktail cruiser. 

Private charters could be anything from a couple wanting to cruise 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.

Some of the many incredible island restaurants we can take you to by boat are Crown Jewel on Great Diamond Island, The Dolphin Marina & Restaurant or Iris Eats in Harpswell, and Island Lobster Company on Peaks Island.

Book Your Portland Maine Boat Cruise

When you book your ticket for one of our private chartered boat trips at Sail Portland Maine, it can be anything you want it to be! There are so many beautiful and unique factors about our beloved Casco Bay – from diverse wildlife like seals and porpoise to the historic Fort Gorges and the sun setting over coastal islands, soak in the beauty that is Portland’s harbor.

For an incredible adventure you’ll talk about for years to come, reserve your trip with us below!