Schooner Sailing Schedule

Schooner J&E Riggin sailing out into Penobscot Bay by Rocky Coast Photography

2020 J. & E. Riggin Sailing Dates

PLEASE NOTE: Links to trip particulars will show information that reflect the current sailing season. Once the current season ends, the next year’s schedule will be updated with proper dates, instructors, and details.

Available Promotion(s): Book your 2020 trip before February 1st for a 5% early booking discount (10% for repeat passengers).

If you are interested in scheduling a charter please call the office at 1-800-869-0604 or use the “Contact Us” form at the top right. All dates are open and available for charter until someone books passage. Call early to get your preferred date.

Please keep in mind that dates and prices are subject to change anytime before December 1st of the previous sailing year. 

Date Trip Description Price per Person
May 22 - 25, 2020 Music & Dance Cruise $895
May 26 - 30, 2020 Maine Lighthouses & Lobsters $813
May 31 - June 3, 2020 Early Summer Getaway $795
June 5 - 8, 2020 Shakedown Cruise $795
June 10 - 13, 2020 Maine Knitting Cruises w/ Mim Bird $955
June 14 - 17, 2020 Maine Knitting Cruises $955
June 19 - 22, 2020 Maine Food Cruise – Cooking with Annie $895
June 24 - 27, 2020 Maine Lighthouses & Lobsters $795
June 29 - July 4, 2020 Schooner Race $1245
July 6 - 9, 2020 Maine Food Cruise – Cooking with Annie $1052
July 10 - 13, 2020 Maine Lighthouses & Lobsters w/ Windjammer Parade $949
July 15 - 18, 2020 Maine Food Cruise – Cooking with Annie $1052
July 20 - 22, 2020 Maine Lighthouses & Lobsters $841
July 23 - 25, 2020 Maine Lighthouses & Lobsters $841
July 27 - August 1, 2020 Music and Storytelling with Geoff Kaufman $1345
August 3 - 6, 2020 Maine Food Cruise – Cooking with Annie $1052
August 7 - 10, 2020 Maine Lighthouses & Lobsters $949
August 12 - 15, 2020 Perseids Meteor Shower Cruise $949
August 16 - 19, 2020 Maine Lighthouses & Lobsters $949
August 21 - 24, 2020 Maine Food Cruise – Cooking with Annie $1052
August 28 - 31, 2020 Summer Isn’t Over Yet $949
September 2 - 5, 2020 Camden Windjammer Festival $949
September 7 - 12, 2020 Maine Knitting Cruises w/ Margaret Radcliffe $1234
September 14 - 19, 2020 Wooden Boat Sail In $1175
September 21 - 24, 2020 Maine Food Cruise – Cooking with Annie $913
September 25 - 28, 2020 Maine Lighthouses & Lobsters $813
September 30 - October 3, 2020 Maine Slow Sewing & Quilting Cruise w/ Rhea Butler $867
October 5 - 8, 2020 Fall Color Getaway $813

Rewards & Savings for Our Loyal Passengers

You have choices when it comes to how you will spend your vacation time. We know it and appreciate that our customers choose us again… and again.

Repeaters say hi to RedOver the years, we have steadily increased the rate of our repeat business. This says—and means—a lot. First, you must enjoy the time you spend with us. Second, you must see the value in the experience we offer. Third, you’re drawn to the excitement of sailing along the coast of Maine… on a historic schooner, to boot!

The way we see it, every windjammer cruise experience is an opportunity to deepen our customer relationships and build value through relevance and real advantages to choosing us. That said, we will continue to offer our Schooner Rewards programs with discounts for early bookings.

  • Riggin Schooner Squad

Earn points to win a FREE schooner vacation. Every time you refer someone to us who books a sailing vacation, you’ll receive 100 points (you also get points for every person in their party—so a family of 5 would earn you 500 points!).  There are several other ways to earn points that you can then use for money off your trip, in our ship’s store, or for certificates to use in our area while you are in town before and/or after your windjammer cruise. Click here for a complete listing of ways to earn points and how to redeem them.

Book Your Trip

Click here to book your Maine sailing vacation.

Welcome Aboard Photo by Rocky Coast Photography

Things to Note:

  • While we feel every sailing cruise is special, we do offer some windjammer trips with events or with a special focus. You can find descriptions under the “Schedule” menu.
  • Keep in mind we board every trip the evening before the date listed between 5 and 6 p.m.
  • To check availability or reserve your cabin please email us or give us a call at 1-800-869-0604.
  • There is a 5% discount if reserved BEFORE February 1 (of the current sailing season).
  • A deposit of $350 reserves a berth on any cruise, the balance is due 6 weeks before your sailing date.
  • Cancellation Policy: Due to our small size, cancellations or rescheduling of dates affect us significantly. We limit the number of guests to a maximum 24 passengers each trip to keep our guests’ experience personal and customized. As a small, family-owned and operated business, this means that every booking is important to ensure an exclusive, authentic experience, and excellent service. All cancellations (no matter the reason) made 8 weeks before your arrival are eligible for a refund less a $150 per person cancellation fee. For cancellations made on or inside 8 weeks before your boarding date any and all payments are non-refundable unless we are able to rebook the entire space. If we are able to fill the entire space, any payments will be refunded less a $150 per person cancellation fee. If your space is not completely filled, any payments are forfeited. If you need to change your trip date and do so before your final payment is made 6 weeks before sailing, any payments made can be applied to a future visit. If the date change happens on or inside of 6 weeks there is a $150 per person change fee.
  • Trip Cancellation Insurance Recommended: Because the Schooner J. & E. Riggin serves a limited number of guests, we strongly suggest that you purchase trip cancellation insurance. If you choose not to purchase trip insurance and an unforeseen event keeps you from being able to travel to Schooner J. & E. Riggin, we will be unable to refund your deposit and/or paid balance as set forth in our cancellation policy. We do not offer insurance directly but do recommend Allianz Travel Insurance. Their toll-free number is 1-866-884-3556  or visit Of course you may use any travel insurance company you prefer. 

We look forward to being a part of your Maine windjammer cruise.

Gift Cards!

Heard on the Docks…

“We want to thank you for all you did to make sailing on the J&E Riggin such a memorable experience. I had looked forward to it so much for so long that I was afraid that the actual experience could not live up to the anticipation. It did!”

~ Harry & Karel S., MO


“We had the time of our lives on the trip, and couldn’t imagine being with a better ship, crew, and shipmates. We enjoyed being entertained by your singing and your jokes in the evening, and just the whole relaxed pace of the week. We appreciated the great cooking and the all-around friendliness of all the crew, a direct reflection of the two of you.”

~ John & Doug P., UT