Cruise Schedule

Here is our most current sailing schedule. Contact us if you have questions, or make a reservation.

BoardingReturnDescriptionLengthPriceBook
May Season Opener
Fri 5/24Mon 5/27Shakedown/Memorial Day Cruise3 nights$525Make Reservation »
Mon 5/27Thu 5/30Weekday Getaway3 nights$525Make Reservation »
June Seasonably longer daylight hours…
fresh breezes…
Thu 5/30Sun 6/2Weekend Getaway3 nights$578Make Reservation »
Sun 6/2Thu 6/6Easy Escape4 nights$656Make Reservation »
Thu 6/6Sun 6/9Weekend Getaway3 nights$578Make Reservation »
Sun 6/9Thu 6/13Schooner Gam4 nights$738Make Reservation »
Thu 6/13Sun 6/16Weekend Getaway3 nights$629Make Reservation »
Sun 6/16Thu 6/20Easy Escape4 nights$738Make Reservation »
Thu 6/20Sun 6/23Weekend Getaway3 nights$629Make Reservation »
Sun 6/23Thu 6/27Easy Escape4 nights$738Make Reservation »
Thu 6/27Sun 6/30Weekend Getaway3 nights$629Make Reservation »
July Lazy days of summer…
Sun 6/30Sat 7/6Schooner Race Week6 nights $937Make Reservation »
Sun 7/7Thu 7/11Easy Escape4 nights$738Make Reservation »
Thu 7/11Sun 7/14Weekend Getaway/Parade of sail3 nights$629Make Reservation »
Sun 7/14Thu 7/18Easy Escape4 nights$738Make Reservation »
Thu 7/18Sun 7/21Weekend Getaway3 nights$629Make Reservation »
Sun 7/21Thu 7/25Easy Escape4 nights$738Make Reservation »
Thu 7/25Sun 7/28Weekend Getaway3 nights$629Make Reservation »
Sun 7/28Thu 8/1Easy Escape4 nights$738Make Reservation »
August Lazy Days of summer continue…
Thu 8/1Sun 8/4Weekend Getaway3 nights$629Make Reservation »
Sun 8/4Thu 8/8Down South Meets Down East4 nights$738Make Reservation »
Thu 8/8Sun 8/11Weekend Getaway3 nights$629Make Reservation »
Mon 8/12Sat 8/17Summer Stretch5 nights$898Make Reservation »
Sun 8/18Thu 8/22Easy Escape4 nights$738Make Reservation »
Thu 8/22Sun 8/25Weekend Getaway3 nights $629Make Reservation »
Sun 8/25Thu 8/29Easy Escape4 nights$738Make Reservation »
Thu 8/29Sun 9/1Windjammer Weekend3 nights$629Make Reservation »
September Warm, clear days, fresh breezes
cool nights, fall colors
Sun 9/1Thu 9/5Easy Escape4 nights$738Make Reservation »
Thu 9/5Sun 9/8Weekend Getaway3 nights$629Make Reservation »
Sun 9/8Sat 9/14Wooden Boat Sail In6 nights$937Make Reservation »
Sun 9/15Thu 9/19Fall Colors/Easy Escape4 nights$738Make Reservation »
Thu 9/19Sun 9/22Fall Colors/Weekend Getaway3 nights$578Make Reservation »
Sun 9/22Thu 9/26Fall Colors/Easy Escape4 nights$656Make Reservation »
Thu 9/26Sun 9/29Fall Colors/Weekend Getaway3 nights$578Make Reservation »
October Final Cruise
Sun 9/29Thu 10/3Timberwind 82nd Birthday!4 nights$656Make Reservation »

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