See our availability on our calendar page. If we are scheduled for a public event, we are not available for a private event. During Wine Sail season, we are unable to accommodate Wine & Food Walks or Bourbon Walks. Read below for answers to frequently asked questions.


2024 Wine sails

Whether you are a group of friends looking for a way to get together or a local business looking for a way to show your team they're appreciated, Wine Sails are the perfect way to get together outdoors for an incredible experience. Summer is a very busy time for us, and we book up very quickly. The 2024 Wine Sail Schedule is currently in progress, with new wine sails added everyday.


Larger Groups

Private events are suited for larger groups because a private wine sail is a full buyout of 38 person capacity x $150 per person.

Larger Groups should purchase all 38 tickets (while they’re still available), and you’ll have a Private Wine Sail that we can customize to suit your needs, such as changing the wine theme. Want to add fresh-shucked oysters? We can do that. Want us to invite a fabulous, Portland chef to create custom food pairings with each of our high-quality wines? They’re busy, too. The sooner we get this on the books, the more likely we can make it happen! Find a Wine Sail, and let us know!

Smaller Groups

Smaller groups will find it more economical to purchase just the tickets they need for one of our many public events.

Small Groups should simply purchase the number of tickets needed to any of our Friday, Saturday, and Sunday Wine Sails and leave the great wine, sailing, charcuterie, and gorgeous scenery to us! We’ll be sure to seat you all together in a section of the boat that’s perfect for the size of your group. We highly recommend purchasing all tickets in one transaction to ensure everyone has a ticket before the event is sold out, and so that we’re aware that a group is joining us.



How many tickets are available to a specific event?
Enter the ticket quantity 50, then add to cart. The system will show you how many are available. If a notification appears noting fewer than 38 tickets are available, that means some tickets have already sold, and that particular wine sail is no longer available for a private buyout. See our full schedule of highly-rated Wine Sails, June - October 2023.

Do you do private events outside of Portland?
We sure do. As long as we are not scheduled for an event in Portland, we can travel to you. We frequently do wine appreciation events in private homes, restaurants, and businesses throughout Maine and New England. We have even traveled as far as Las Vegas, New Jersey, San Diego, and Vermont for our customers. Just let us know what you are thinking and I am sure we can make something work based on schedules and availability.

How far in advance should we book?
It is never too soon to book your private event. The more advance notice, the more likely you will have your preferred day and time.

More Frequently Asked Questions