When the weather is warm in Portland, there is no better place to be than out on the stunning Atlantic ocean. Sail Portland Maine offers intimate Casco Bay private harbor cruises that give you a personal chartered experience like no other. Before you book your trip with us this summer, be sure you’re prepared with answers to any questions you may have!
What type of boat will we be taking out?
The Calista Ann is Sail Portland Maine’s classic motor yacht and private charter boat, offering a comfortable and intimate way to explore Portland Harbor and Casco Bay. She’s ideal for private cruises, sunset trips, celebrations, corporate outings, and customized coastal adventures. Guests can bring their own beverages, with a cooler and ice provided, and enjoy amenities including a private restroom and Wi-Fi while taking in the scenery of Maine’s coast.
How many people can go on each sail?

The Calista Ann can accommodate up to a group of 12 (or a minimum of 8).
Ours is one of the smallest chartered cruises in town, which is part of what makes Sail Portland Maine so special! Our goal is to give you an intimate, private trip that is set apart from the standard, fully-packed chartered trips of larger companies. If you have fewer than 6 people in your party but want the opportunity to have the boat to yourselves, you can also book a private charter based on availability.
What is the policy for alcoholic beverages?
Adult beverages are welcome on board! Feel free to BYOB along with any food you’d like. Is there any better way to take in the gorgeous coast of Maine than with a refreshing beverage in hand? We don’t think so!
How long are the chartered trips?
Our chartered trips typically last about two hours, though we can accommodate longer sails by request.
Where do I book a reservation for a charter?
You can easily make a reservation for our trips on our website or give us a call directly at 207-200-6650 to schedule.
Please note, you may cancel your reservation without charge up to 48 hours prior to your scheduled departure, but any cancellations within that 48 hour period will require you to pay the full amount of the charter. If there is inclement weather and the Captain must cancel the trip, you will not be charged.
Who charters at Sail Portland Maine?
Captain Ian has many years of experience crewing and captaining ocean-bound vessels, from private sailing yachts to commercial supply boats (in some cases, even yachts for royal families!), so you can expect to hear some fascinating stories from his journeys as you cruise.
At Sail Portland Maine, we offer crowd-free, professionally-captained excursions so you can enjoy an intimate experience you’ll never forget. Enjoy quality time with your loved ones, have a cold beverage, and take plenty of photos while aboard the Calista Ann. If you have any questions about booking one of our Casco Bay private harbor cruises for this summer’s next big adventure, please contact us!