Maine Sailing Charters

Ben Krebs Photography

Family Reunions, Class Trips, Weddings at Sea

By its very nature, sailing is engaging and relaxing and our historic sailing ship offers you an unrivaled setting and experience. Your group will be in for the adventure of a lifetime.

Whether we are racing with other schooners across the bay, exploring the beach at a lobster bake, or sitting on deck listening to music being performed by the captains and crew, your chartered windjammer trip is sure to leave everyone with smiles and unequaled memories. It’s an adventure for kids and adults alike. There is something for everyone to do whether it’s helping to sail, exploring uninhabited islands, joining in on a scavenger hunt, visiting quintessential coastal villages, or simply finding a space on deck to sit back and relax and read, knit, play cards, or even take a nap. We find the simplest things are often the most luxurious.

Come explore the coast of Maine from the best side – the sea. Imagine a three to six hour tour, an overnight, or even a week-long charter gliding along the rocky coastline and spruce clad islands; seeing seals, porpoise, and bald eagles, lighthouses and other tall ships, and enjoying classic food focusing on local ingredients food prepared with fire and soul on the ship’s wood burning stove.

Your charter is an all inclusive package including crew, three handmade meals a day, a traditional Maine lobster bake (on charter 3 or more days) and of course the spectacular Maine scenery.

Maine Windjammer Charter Details

  • All charters are custom planned for you and your group
  • All charters receive a discounted group rate – call for details
  • Capacity of 24 overnight guests and 45 day sail guests
  • For larger groups, we partner with other schooners to accommodate your numbers
  • Minimum of 3 hours for a day sail

We are proud to share that over 75% of our educational and school charters have returned to sail again.

Schooner Charters - Youth Groups, Class Trips, Weddings, Corporate retreats


Charter a windjammer

2022 dates are now open for charter requests

Charter the Maine Windjammer J. & E. Riggin for:

  • Family reunion
  • Knitting (or another creative) retreat
  • Culinary getaways and travel
  • Photography excursion
  • Class reunion (Senior class trip, graduation from 8th grade)
  • Nautical wedding and vow renewals at sea
  • Birthday/anniversary celebration
  • Celebration of life
  • Boy Scout and Girl Scouts
  • Sailing or yacht club
  • Team building
  • Youth group trip
  • Inspirational retreat
  • Alumni get-togethers (college reunion)
  • Non-profit fundraising trip


Heard on the Docks…

“I had anticipated stepping on board for months.

The ship seemed legendary and intriguing.  Every thing was perfect and useful.  The wood had copious layers of varnish, permeated to perfection.  We explored our cabins to find tiny quarters.  After a few days, the rooms did not feel so cramped and were actually quite comfortable.

At the beginning of our trip I felt like a visitor on the boat; towards the end, I felt a part of it.  We were extraordinarily lucky with every aspect of our trip:  perfectly timed weather; blue skies during the day and torrential down pour and thunderstorms at night; the wind was abundant but not so severe that reefing the sails was necessary; I never had to apply bug spray during the trip!

Every aspect of our trip was tremendous and opportunities were endless!  The captain and crew were cordial and very willing to teach anyone who wanted to learn. The captain taught me to find our exact location on the chart using only three points of reference.  He also taught me six commonly used knots including the bowline, clove hitch, sheepshank, two turns and a half hitch, taught line hitch, and square knot.

The food was sensational and was comparable to any restaurant I have dined in and lived up to its high reputation.  We never ate the same meal twice, although there was always peanut butter and jelly for anyone with bland taste buds.  Every morning on deck there was tea and hot chocolate.

When I left, I felt like I was forgetting something or I was not where I was supposed to be.  I felt like I belonged with the ship.”

~ Ian M. 8th grade student