Windjamming Off Maine

By John Reeves
This item appears on page 27 of the April 2021 issue.

 As someone who has visited over 100 countries, I highly recommend taking a week-long windjammer cruise off the coast of Maine.

My wife and I have done this four times, the first trip around 30 years ago. It’s always a delightful experience, though it bears no resemblance to a traditional cruise. (The word “cruise” evokes certain experiences to seasoned travelers, but anyone expecting anything remotely similar to that will be disappointed.)

The scenery off the coast of Maine is spectacular, the area dotted with many scenic islands that have small, quaint villages. There is a nice balance of time between being out on the water and exploring the numerous interesting hamlets. There is no set itinerary, since the route depends upon which way the wind is blowing.

Sailing is smooth because most of the sailing is not done in the open ocean. If you google “Penobscot Bay, Maine,” you’ll see that the giant bay and others nearby are filled with islands that provide a buffer from the open ocean. The cruising grounds basically run from Rockland northeast to Bar Harbor.

About a dozen windjammers can be seen in the area, eight of which belong to the Maine Windjammer Association ( Most ships are ported in either Camden or Rockland, on Penobscot Bay, and each is owned by its captain.

We have found the captains to be very friendly. One of these is Captain Barry King, owner of the schooner Mary Day (Camden, ME; 800/992-2218, We sailed with him and his wife, Jen, about 5½ years ago. Lovely people!

Although the ships have similarities, each is unique. On most, the deck measures roughly 90 feet, and it’s about 25 feet across the beam, so you don’t feel cramped. The majority carry from 20 to 40 passengers and a crew of four to seven, which can consist of captain, first mate, deckhands, cook and assistant cooks.

Cabins are snug, each with either a double bed or bunks and a sink with running water. Heads (toilets) and showers are available on all vessels. And, as they say in Maine, the food is “wicked good.”

Passengers are invited to help with the sailing — hoisting sails, etc. — as much or as little as they want.

Depending on the ship, the length of the cruise and the week selected, rates can range from $675 to $2,500 per person. The sailing season runs from late May to mid-October.

Jackson, CA