Schooner Sailing Schedule

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

2023 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 2023 trip before February 1, 2023 for a 5% early booking discount (10% for repeat passengers). 

*Schooner discounts do not apply to the 207 Creatives Rug Hooking Getaway. Please go to for details, pricing, incentives, and discounts.

Discounts and promotions are available for new reservations only. Only one offer can be applied to your reservation. Promotions may not be combined with any other offer, discount, or charter rate. Cancellation of trip and re-booking with a new discount or promotion is prohibited.

Sailing Charters?  If you are interested in scheduling a sailing charter please call or email.  If you don’t see a date on the schedule that is just perfect for you, we are happy to work with you to make it happen.

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

Date Trip Description Price per Person
May 21 - 25, 2023 Shakedown Cruise $935
May 26 - 30, 2023 Live Music Cruises w/ Bennett Konesni & The Gawler Family Band $990
May 30 - June 2, 2023 Maine Lighthouses & Lobsters $795
June 3 - 7, 2023 Early Summer Getaway $935
June 8 - 13, 2023 Windjammer Rendezvous $1055
June 14 - 18, 2023 Maine Knitting Cruises w/ Mim Bird $994
June 19 - 22, 2023 Maine Sip & Sail Cruise w/ Craft Cocktails by Lara Nixon $825
June 22 - 26, 2023 Sawmill Creek Fiber Events Knitting Cruise
June 27 - July 1, 2023 Maine Lighthouses & Lobsters $935
July 2 - 8, 2023 The Great Schooner Race $1356
July 9 - 13, 2023 Maine Sip & Sail Cruise w/ Craft Beers of Maine $1140
July 14 - 17, 2023 Kids & Family Cruise $985
July 18 - 22, 2023 Maine Lighthouses & Lobsters $1125
July 23 - 29, 2023 Live Music Cruises w/ Geoff Kaufman $1392
July 30 - August 4, 2023 Live Music Cruises w/ Bennett Konesni & Co. $1330
August 6 - 9, 2023 Maine Lighthouses & Lobsters $985
August 10 - 14, 2023 Skygazing Cruises w/ Perseids Meteor Shower $1125
August 15 - 19, 2023 Maine Lighthouses & Lobsters $1125
August 20 - 24, 2023 Rug Hooking Cruise w/ Rebecca Martin $1795
August 25 - 28, 2023 Summer Isn’t Over Yet $985
August 29 - September 2, 2023 Camden Windjammer Festival $1000
September 3 - 9, 2023 Maine Knitting Cruises w/ Margaret Radcliffe $1282
September 10 - 16, 2023 Wooden Boat Sail-In $1220
September 17 - 21, 2023 Scenic Maine Photography Cruise w/ Sean & Tracy Sheppard $1012
September 22 - 26, 2023 Maine Lighthouses & Lobsters $995
September 27 - October 1, 2023 Culture & Cuisine w/ Chef Sam Collins $1015
October 2 - 6, 2023 Maine Sip & Sail Cruise w/ Craft Cocktails by Lara Nixon $1033
October 7 - 11, 2023 Fall Foliage Cruise $995

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.

Over 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 offer discounts to returning guests who book early for their favorite cruises. 

Book Your Trip

Click here to book your Maine sailing vacation.

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.
  • We board every trip the evening of the first date listed between 5 p.m. 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 1st (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 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. *In the case of natural disaster or pandemic, please understand that we are a micro-small business and we are unable to issue a refund.  (updated 5/2020)
  • 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