PRIVATE
WINE SAILS
An Unforgettable Experience for Your Group
Looking for an extraordinary way to celebrate with your group? Host a private Wine Sail with Wine Wise and treat your guests to a one-of-a-kind experience that blends beautiful wines with the beauty of Casco Bay.
Whether you're planning a company outing, birthday celebration, retirement gathering, or wedding party, our private Wine Sails offer the perfect combination of sophistication and relaxation. With space for up to 42 guests, this is a rare opportunity to create lasting connections while sipping sommelier-selected wines and enjoying the stunning Maine coastline.
It’s not every day you can host an event on the water, blending the best of Maine’s coastal charm with world-class wines.
Incredible Wines
Each Wine Sail features thoughtfully chosen wines that reflect the region and season, ensuring a memorable tasting experience. Our sommelier will guide you through each pour, sharing insights and stories behind the wines, making it as educational as it is enjoyable.
A Breathtaking Backdrop
Glide through the calm waters of Casco Bay aboard the immaculate 74-foot tall ship, Frances, soaking in picturesque views and the peaceful ambiance of sailing with views of Maine lighthouses, calendar islands, and waterways.
Wine Sails – Five beautiful wines and our cheese and charcuterie selections. (Capacity: up to 42 guests)
Wine & Oyster Sails – A classic pairing featuring 500 Maine oysters. (Capacity: up to 38 guests)
Chef Series Wine & Food Sails – A exclusive gourmet experience with a great Portland chef carefully preparing a course to complement each wine. (Capacity: up to 42 guests)
Booking Details:
Duration: 2 hours
Availability: June 13 - October 19, 2025 (dates book quickly, so secure your sail early!)
How to Book: Visit our calendar to check availability and review our FAQs below. Purchase all tickets to an existing Wine Sail or contact us directly to arrange your private wine sail on a different day and time.
Create an unforgettable experience on the water for your guests. Let’s plan your private Wine Sail today!
Larger Groups
Private Wine Sails are a full buyout and are best suited for larger groups. Purchase all tickets to any of our events or reach us for an optional day and time.
Smaller Groups
Purchase just the number of tickets you need to any of our events. Purchase all tickets in one transaction—to ensure everyone has a ticket before it sells out.
FAQs:
How much is a Private Wine Sail?
A private event is a buyout. The cost is the number of attendees allowed multiplied by the ticket price; Wine Sails = 42 people × $150, Wine & Oyster Sails = 38 people x $175, and Chef Series Wine & Food Sails = 42 people × $185.
For smaller groups, purchasing just the number of tickets you need for our highly-rated public events often makes more sense. Purchase all tickets in one transaction to ensure everyone in your group has a ticket before the event sells out.
Can I book a Private Wine Sail on a weekend?
Yes, if all tickets are available, you may purchase them all to have the Wine Sail as private. It also may be possible for us to add a 12-2 pm Private Wine Sail for you if we are not already booked.
How do I determine how many tickets are available to a specific event?
Go to the event page where you would purchase tickets, enter ticket quantity 50, and then add to the cart. A pop-up will display how many tickets are available. If all tickets are available then you can purchase them and have the event as private. If fewer than 42 tickets (38 for Wine & Oyster Sails) are available, some tickets have already sold, so that particular wine sail is no longer available for a private buyout. See our full schedule of highly-rated Wine Sails, June - October 2025.
How far in advance should we book?
You should book as soon as you know you’d like to book! Our schedule fills quickly.
Do you do private events outside of Portland?
We sure do. We can travel to you as long as we are not scheduled for an event in Portland. 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.
