Schooner Gam ~ 2nd Week of June

• Kick off the summer season with a windjammer gathering of the entire fleet! Relive the age of sail during this quiet rendezvous of more than a dozen 19th-century-style sailing ships. Location is determined by the weather of the day! Raft-Up!

Boothbay Windjammer Days ~ Last week of June

• Participate in a grand sail parade through picturesque Boothbay Harbor. Windjammers come from all over the coast of Maine to participate in this exciting early-season event. Shoreside activities include music, fireworks, festival activities, a street parade and food vendors.

Great Schooner Race ~ 1st Week of July

• More than two dozen tall ships gather for an exciting all-day race in which guests may participate. This year marks the 32nd anniversary of the Great Schooner Race, North America's largest annual gathering of tall ships! Raft-Up!

Camden Windjammer Weekend ~ Labor Day Weekend

• The fleet gathers in picturesque Camden Harbor for festivities reminiscent of the days when hundreds of coastal schooners lined the waterfront. Festivities include a parade of sail, flag-raising ceremonies, live music, dancing and fireworks. Raft-Up!

Wooden Boat Cruise ~ 2nd Week of September

• The fall gathering of the fleet takes place in Brooklin, Maine, headquarters of WoodenBoat Magazine and WoodenBoat School. Now in its 23rd year, the event includes refreshments, live music, tours and a harbor full of historic schooners.

Weekend Getaway (3 Days) and Easy Escape (4 Days) Are Our Specialites . . .

• With the largest number of 3 & 4 day cruises available, the Timberwind offers Maine vacationers the opportunity to sail aboard a majestic Windjammer for a shorter duration. We know you have less time available, and we have created schedules to accommodate you without any compromising to the experience.

Summer Stretch Sails

• If you have ever sailed on one of our shorter cruises and loathed returning to port on the final day then you will understand exactly why we have added a couple of our new 5 day cruises this year. These cruises are designed for those of you that for the last decade have said, "I wish we could stay just one more day! I'm not ready to go back home yet!" Just for you, we have stretched these cruise an extra day.