PRIVATE
WINE SAILS
An Unforgettable Experience for Your Group
Looking for an extraordinary way to celebrate with your group? Whether you're treating your high-performing team, celebrating a milestone, or planning an iconic gathering—our highly rated Wine Sails are the summer experience you'll want to book.
Our Wine Sails are among the most exceptional experiences you can have on the coast of Portland, Maine, with space for up to 42 guests. You’ll sail through pristine Casco Bay aboard the immaculate tall ship Frances, enjoying five fantastic sommelier-selected wines and panoramic views of lighthouses, island cottages, and historic forts. Our one-of-a-kind Wine Sails are easy to plan, whether you're booking just a few tickets or the whole boat.
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
Enjoy five beautiful wines paired with our cheese and charcuterie selection.
Capacity: Up to 42 guests
Chef Series
Wine
& Food SailS
Five delicious courses crafted by one of Portland’s acclaimed chefs, complemented by five beautifully paired wines. Intimate, open-air, and unlike anything else on the water.
Capacity: Up to 42 guests
Wine & Oyster Sails
Indulge in sommelier-selected wines along with 500+ Maine oysters, freshly shucked on board.
Capacity: Up to 38 guests
Booking Details:
Duration: 2 hours
Availability: June 13 - October 19, 2025
Location: Portland, Maine
Note: Wine Sails book quickly! Book now to ensure availability.
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 full buyout. The cost is based on the maximum number of attendees multiplied by ticket price, plus $400 gratuity for The Captain and her crew.
Wine Sails: 42 guests × $150 + gratuity = $6,700
Wine & Oyster Sails: 38 guests x $175 + gratuity = $7,050
Chef Series Wine & Food Sails: 42 guests × $185 + gratuity = $8,170
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?
If all tickets are available, you may purchase them to ensure the Wine Sail is private. With enough advance notice, we may also be able to create a 12-2 p.m. Private Wine Sail.
How do I determine how many tickets are available for a specific event?
Head to the event page, enter ticket quantity 50, and add to cart. A pop-up will display how many tickets are available. If fewer than 42 tickets (38 for Wine & Oyster Sails) are available, that particular wine sail is no longer available for a private buyout.
How far in advance should we book?
Book as soon as possible! Wine Sails fill quickly, and our availability is limited.
Do you do private events outside of Portland?
We sure do! We can travel to you so long as our schedule permits. 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.
View more Frequently Asked Questions here.
