What to Expect from Sail Portland Maine’s Private Harbor Cruises

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 sailing 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 Eleanor Hawkes is a traditional Friendship sloop, also sometimes referred to as a Muscongus Bay sloop or lobster sloop. This boat is a traditional style that got its name from its origin in Friendship , Maine. Created in 1880, the Friendship sloop was the traditional fishing and lobster boat in the state until the early 20th century. Sailing on the Eleanor Hawkes offers you a unique opportunity to experience some of Maine’s rich history.

How many people can go on each sail?

Casco Bay private harbor cruises

The Eleanor Hawkes has room for up to 6 people, making it one of the smallest chartered cruises in town. This is part of what makes Sail Portland Maine so special! Our goal is to give you an intimate, private sail that is set apart from the standard, fully-packed chartered sails 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. We also offer sails trips with drinks provided – on Thursdays we feature delicious local craft beers and on Saturday we do a sunset cruise with crisp rose. 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 sail trips?

Our chartered sails typically last about two hours, though we can accommodate longer sails by request.

Where do I book a reservation for a sail?

You can easily make a reservation for our sailing 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.

captain ianWho charters the Eleanor Hawkes?

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 sailing 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 Eleanor Hawkes. 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!

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