Thinking out of the box, a windjammer cruise can be a custom adventure to meet your needs. Over the years we have seen it all; weddings, family reunions, club outings, corporate retreats, team building, you name it. We see these special charters as both a challenge and an opportunity to share the beauty of both Penobscot Bay and our historic schooners while doing our best to enhance your theme or special requirements.


Windjammer weddings are very popular and our schooners can accommodate up to one hundred people for a four hour sail. We can provide everything from hors d' oeuvres to a lobster dinner and are happy to help arrange for flowers, drinks or a wedding cake. Our services include assistance if required for wedding photographers, musicians and shore side accommodations. The captain will officiate the ceremony and all of your worries can be left behind.

Many of our weddings are multi day events with ceremonies on secluded island beaches or quiet sunset anchorages. Some provide a romantic backdrop with day sails for guests and a floating B&B for private island weddings that offer limited accommodations. Read about Allysa & Seth's Amazing Island Wedding


A Windjammer Cruise makes for a great family reunion!
Family reunions are a great way to enjoy a windjammer vacation. There is plenty of activity and everyone is close by. Your group may have ties to Maine and require certain destinations. Chartering the vessel will give the dynamic of the group the ability to choose the schedule or the menu depending on your needs.


Boy Scouts learning to tie knots
We have had charters with volcanologists from MIT where each day we explore a different geological site. Other trips include team building adventures for hospital administrators, high tech executives, even Burton snowboard sales staff. Faculty cruises, church groups, scout troops, alumni gatherings, class trips and dozens of other organizations have enjoyed our schooners as a unique and memorable way to share an experience that is wholesome, refreshing and uniting.

When you charter a windjammer, it's up to you where we go, how long we sail, when we stop, etc. When you have the full boat there are also no age restrictions. Of course there are logistical limitations and that's where our expertise comes in. We can help you plan an itinerary that will give your guests the best trip possible.


"When a group or a bride and groom come to me with their idea for a perfect event, sometimes it can be a challenge juggling existing schedules. It's also exciting as we collaborate to layout all the possibilities. Often I can suggest options that the customer would have never thought of. It's a great feeling of satisfaction when we have been able to put together an experience for our passengers and their guests that was all that was hoped for, and in many cases exceeded their expectations." Captain Ray