When the weather is warm, there isn’t any better place to enjoy yourself than gliding through the glassy waters of the Casco Bay during a boat charter in Portland, Maine. Sail Portland Maine is here to give you a personal boating experience unlike any other! Our day trips take you through the harbor, where you’re likely to see some of the diverse wildlife, historic structures and lighthouses, breathtaking coastal islands, and much more.

Our Unique Boat Charters in Portland, Maine

We offer two-hour public or private chartered trips with several trip options for you to choose from throughout the day or evening.

Choose your Perfect Casco Bay Trip

Meet Our Boats

Eleanor Hawkes (Sailboat) → Book a Trip on the Eleanor Hawkes

The Eleanor Hawkes has space for a group of up to 6 people, making it one of the smallest chartered cruises in Portland – and thus, one of the most crowd-free and intimate experiences on the harbor!

  • 12:00 PM – 2:00 PM: $85 per Person/$500 Private Charter
  • 3:00 PM – 5:00 PM: $85 per Person/$500 Private Charter
  • 6:00 PM – 8:00 PM (Fall hours vary): $85 per Person/$500 Private Charter

Calista Ann (Classic Motor Yacht) → Book a Trip on the Calista Ann

Our Classic Motor Yacht, the Calista Ann, is the perfect picnic boat. It has space for up to 12 guests to keep that intimate experience but also allows you the space to enjoy your own beverages and snacks.

All charters on Calista Ann are private no matter how many people are in your party. If your group would like more than 2 hours, additional rates apply(Call to book extra time). Please contact us or call directly for any questions.

  • 12:00 PM – 2:00 PM: Private Charter starting @ $720
  • 3:00 PM – 5:00 PM:   Private Charter starting @ $720
  • 6:00 PM – 8:00 PM (Fall hours vary): Private Charter starting @ $720

boat charter portland maine


Sunsets in Portland, Maine can also be pretty incredible, which makes our sunset cruise at Sail Portland Maine a no-brainer! Whether you’re a hopeless romantic wanting to share a special evening with your significant other (or even having thoughts of proposing!) or a group simply looking to enjoy the show, a Casco Bay sunset will give you an experience that is second-to-none.

Book Your Cruise with Sail Portland Maine!

Make the most out of the summer season with the best boat charter in Portland, Maine. Whether you’re visiting from out of town, planning a unique, intimate event, or simply spending time with loved ones, let us provide you with the best possible chartered boat experience. For a memory you’re sure to reminisce about for years to come, book your trip with us at Sail Portland Maine today!

Book Your Trip with Sail Portland Maine