5 & 6-Night Trips
June
June 12th- June 17th | 5 Nights | Gathering of the Fleet
One of our most popular trips each season, Reese Fulmer and the Carriage House Band will join us again!
The four-piece band will leave you humming and tapping along with their modern folk music. Informal sets will be played throughout the trip, with the fan-favorite performance during the Schooner Gam. The Schooner Gam is the first fleet gathering of the Maine Windjammer Association of the year. On one of the evenings during the trip, all nine vessels will spend a night (weather permitting) rafted together. Guests of all the boats get the chance to boat-hop from deck to deck and participate in the largest raft-up of traditional tall ships on the East Coast.
$1,910 Per Person | Book Here
July
July 4th- July 10th | 6 Nights | Race Week
Take part in one of the largest traditional races of schooners in North America!
Get your competitive edge on and join us as we participate in the 47th Annual Great Schooner Race. As a part of the Windward class, we'll race for the claim over the cup again. The race is the second event of the year for the Maine Windjammer Association, and there is no shortage of competition. Starting the night before the "big boat" race, the crews participate in the small boat race. Watch as our crew fights to defend its title for the fourth year in a row. The following morning, the race course is determined, and each class starts over the line. Cross your fingers for loads of wind; we will not hold back and charge to cross the finish line first.
$2, 048 Per Person | Book Here
July 20th- July 25th | 5 Nights | Coastal Classics
Experience peak summer weather in Maine... from the water!
Five nights give us plenty of time to explore some of our favorite bays in the area. Come with us as we follow the shorelines of spruce-studded islands and anchor by quaint fishing villages. Paired with our farm-to-table creations coming out of the galley, this is a true windjamming trip with no set itinerary.
$1,934 Per Person | Book Here
August
August 9th- August 14th | 5 Nights | Coastal Classics
Experience peak summer weather in Maine... from the water!
Five nights give us plenty of time to explore some of our favorite bays in the area. Come with us as we follow the shorelines of spruce-studded islands and anchor by quaint fishing villages. Paired with our farm-to-table creations coming out of the galley, this is a true windjamming trip with no set itinerary. Beat the summer crowds and get the full New England experience in Penobscot Bay and beyond.
$1,934 Per Person | Book Here
August 15th- August 21st | 6 Nights | Unscripted Adventure
Six nights, no itinerary; where can we go?!
We're going back to the basics and setting sail on a classic Maine Windjamming adventure. Six nights give us plenty of time to explore Penobscot Bay and beyond. Let's see what we can see and where we can go! Perhaps a visit to the iconic Mt. Desert Island and the stunning Valley Cove, or perhaps a visit to the spruce-studded Isle au Haut. The only thing we have planned for this trip is good cooking and even better company.
$2,048 Per Person | Book Here
September
September 12th- September 18th | 6 Nights | WoodenBoat Fleet Meet-Up
Join us for the last Maine Windjammer event of the year!
Sail with us as we anchor in Brooklin, Maine, with the whole fleet for one final time in the season. Home of the WoodenBoat School and Magazine, we'll get the chance to be in the presence of legendary vessels. This six-night trip is typically our last chance in the season to get as far Downeast as possible. Watch from the water as the fall foliage starts to turn, the wind starts to pick up again, and nights are kept warm by the wood-burning stove.
$1,740 Per Person | Book Here
Booking and Cancellation Policy
All our cabins accommodate two; Cabins F and G can be guaranteed as single occupancy for an additional $60 per night. Upper and Lower Cabins can be booked privately for single occupancy or shared at the per-person rate. 35% of your trip cost is due at the time of booking, with the balance due 8 weeks before the trip date. A full refund, less a $50 per person fee, will be provided until the balance-due date. Should you cancel with less than 8 weeks’ notice, your payment, less the $50 fee, will be refunded only if a new guest books in place of your cancellation. Re-bookings are subject to a $50 per-person fee. Prices listed do not include online booking provider costs. All bookings are subject to change at any time.
Payment Methods
Payments may be made by check, Visa, MasterCard, Discover, or American Express.