One of the Most Unique Fall Experiences in Maine: Sailing Aboard the J. & E. Riggin

Fall is undoubtedly my favorite time of year! And last year I kicked off the season with an experience unlike anything I had ever done before! I spent three days living aboard a historic schooner, sailing along the beautiful coast of Maine on a Maine windjammer cruise.

It was truly one of the most special travel experiences I’ve ever had! From spending our days sailing along the coast to stopping in charming coastal towns, enjoying incredible meals on board, and watching the fall colors pass by from the water, the entire experience felt so unique.

If you’ve ever contemplated doing something like this before, I’m about to convince you why sailing aboard the Schooner J. & E. Riggin deserves a spot on your fall bucket list.

For experiencing Maine by land, read this post next: Things To Do in Maine: The Ultimate Summer Bucket List

A Little History on the J. & E. Riggin

Before I get into what the experience of actually living and sailing aboard the J. & E. Riggin is like, I think a little history is important! Because this isn’t just a sailboat created for tourists. The J. & E. Riggin has been sailing for nearly 100 years.

The two-masted schooner was built in Dorchester, New Jersey, in 1927 by Charles Riggin. It was named after his two sons, Jacob and Edward. It was originally built as an oyster dredger and was designed for both speed and maneuverability. In fact, in 1929, the J. & E. Riggin won the only official oyster schooner race ever held on Delaware Bay.

After decades of working as a fishing vessel, the schooner was eventually retired. Then, in 1975, Dave and Sue Allen of Rockland, Maine, purchased the J. & E. Riggin and began the lengthy process of restoring her. By 1977, she had been transformed into the Maine windjammer that travelers can experience today.

The J. & E. Riggin now has 11 cabins and can accommodate up to  24 guests on multi-day sailboat trips along the Maine coast. In 1991, she was designated a National Historic Landmark in recognition of her significance to American maritime history.

One of the coolest things about sailing aboard the J. & E. Riggin is that she still operates primarily under sail—there is no inboard engine! The crew relies on the wind to travel along the coast, using a small motorized yawl boat when needed to navigate harbors or when conditions are calm. Even the sails are raised by hand, making the entire experience feel like a true step back in time.

Meet Your Hosts

Today, the J. & E. Riggin is owned and operated by Captains Justin Schaefer and Jocelyn Schmidt, who officially became the schooner’s stewards in 2021. Justin’s connection to the Riggin actually began when he first sailed aboard at just 12 years old. He later returned to work as an apprentice, deckhand, and eventually mate before he and Jocelyn took ownership years later.

Jocelyn found her love for sailing while studying history in college and went on to spend years sailing and teaching aboard different schooners. Today, Justin serves as Captain while Jocelyn is both Captain and Chef—and the incredible food is a huge part of the experience! They even grow produce and herbs and keep bees at their home in Rockland, bringing some of those homegrown ingredients aboard.

Together, they’ve continued the tradition of the J. & E. Riggin while creating a really special, personal experience for the guests who come aboard.

When Can You Sail Aboard the J. & E. Riggin?

One of the great things about sailing with the J. & E. Riggin is just how many opportunities there are to experience it. Their sailing season typically runs from the end of May through the beginning of October, with an average of around six different sails each month.

Trips range from 3 to 6 days and nights, giving you plenty of options depending on how much time you want to spend on a sailing vacation in Maine. They also offer a variety of themed trips throughout the season based on different interests. You’ll find everything from knitting cruises to lighthouse and lobster cruises, so there really is something for everyone!

I personally joined their Maine windjammer fall foliage cruise at the beginning of October, and it was such a unique way to kick off my favorite season., and it was such a unique way to kick off my favorite season. Sailing along the coast of Maine, peeping fall colors, made an already incredible experience that much more special!

What Is It Actually Like to Live Aboard a Historic Schooner?

I honestly didn’t know what to expect going into this experience, and I’m not going to sugarcoat it: this is not a “luxury” experience. You are living aboard a historic schooner! The cabins are small, the bathrooms are a little less than ideal, and you can’t expect perfect Wi-Fi or all the comforts you would find in a hotel.

With that being said, this was still one of the most special and unique experiences I’ve ever had. My best way of describing it is: if you can go camping, you can absolutely do this! I would consider it slightly “roughing it,” but what you may sacrifice in cabin space and bathroom amenities, you more than make up for with incredible views, amazing food, and an experience unlike anything else.

A Few Things to Know Before Staying Aboard

Here are a few things I would keep in mind when it comes to actually living aboard the schooner:

• The cabins and beds are very small. The less you pack, the better! Bring only what you really need because you won’t have much room for extra belongings. Packing light will make your living situation so much easier
• You’ll spend very little time in your cabin. Most of your time will be spent above deck, which is where everyone tends to congregate and where you’ll enjoy the best views. Your cabin is really just your cozy little place to sleep at the end of the day
• There is a coffee and tea station every morning and evening. It’s the perfect thing to wake up to, and I promise your morning cup of coffee tastes even better when you’re drinking it on the water while watching the sunrise

• There are USB outlets for charging your devices, so make sure you bring the proper cords. I was actually surprised by how often we had cell service while sailing, but I definitely wouldn’t rely on it throughout the trip
• Bring Dramamine or your preferred motion sickness medication. Most of our sailing was relatively smooth, but we did have one day with rougher waters, and I was very happy to have it with me
• Sheets, blankets, and linens are provided, so you don’t need to worry about packing your own bedding

What Does a Typical Day Aboard the J. & E. Riggin Look Like?

A day aboard the J. & E. Riggin is magical, to say the least. My body naturally started waking up around sunrise, and I wasn’t the only one. Most of us would make our way up to the deck as pastel colors began painting the sky, grab a cup of coffee or tea, and simply sit and watch the sunrise over the water. Truly such a beautiful way to start the day!

Morning & Afternoon Aboard

After eventually getting myself ready, it was time for breakfast. And the food was always something to look forward to. One of my favorite breakfasts we had was the shakshuka! From there, the late mornings and early afternoons were incredibly relaxing. The sails would go up, which we were actually able to help with, and then we would start sailing. There was something so peaceful about simply being out on the water with nowhere else to be. You could take in the views, chat with everyone on board, or find a comfortable spot to lounge with a book. It was meditative, relaxing, and such a nice opportunity to completely disconnect.

Exploring Along the Maine Coast

While a lot of our time was spent sailing, there were also opportunities to get off the schooner and explore. One afternoon after lunch, we climbed aboard the ship’s smaller boat and headed to land, where we visited a charming little fishing village. We had some time to walk around, pop into a few shops, and explore before heading back. And of course, whenever we returned to the boat after an excursion, snacks were waiting for us!

Dinner & Evenings Aboard

Dinner was always a main event. My favorite meal of the entire trip was an incredible lobster bake on a gorgeous uninhabited island. I still don’t know how the crew managed to transport everything from the schooner to the island, set everything up, cook an entire meal, and create such an incredible experience for us. We dined as the sun went down, and I shamelessly ate three lobsters that night.

Our evenings were just as relaxed as the rest of the day. After dinner, we would wind down, spend a little more time together, and eventually head to our cabins for a pretty early bedtime. After a full day in the fresh air, there was something incredibly peaceful about crawling into bed and feeling the gentle rocking of the water put you to sleep.

No two days aboard are going to look exactly the same, and I think that’s part of what makes this experience so special. You’re sailing, after all! Where you go and what you do can depend on the wind and weather, but the slower pace of each day, good food, beautiful scenery, time on the water, and little adventures along the way are all part of the magic.

Let’s Talk About the Food

What some people may not realize about this excursion is that it’s also a foodie experience! As I mentioned earlier, Jocelyn, one of your captains, is also the chef, and she is phenomenal at what she does. Each meal is created with so much thought and attention to detail that you’ll quickly forget you’re eating aboard a historic schooner. To be completely honest, the food was better than what I’ve had on some luxury cruises!

Part of what makes the food so special is the emphasis on fresh, local ingredients. Jocelyn and Justin have their own gardens back home in Rockland, where they grow produce, herbs, and edible flowers that make their way into meals aboard the Riggin. They also keep bees, producing their own honey! That connection between what they grow at home and what eventually ends up on your plate makes the dining experience feel even more personal.

And there was no shortage of food. From beautiful breakfasts and freshly baked treats to lunches, afternoon snacks, and incredible dinners, every meal gave us something new to look forward to. They were also able to accommodate dietary restrictions while still creating meals that felt thoughtful and delicious. Between the food itself, the fresh ingredients, and getting to enjoy it all while sailing along the coast of Maine, the meals ended up being one of the biggest highlights of the entire experience for me.

Do You Need Sailing Experience?

I’d hate for anyone to think they need sailing experience to do something like this, because you absolutely do not need any prior sailing knowledge to come aboard the J. & E. Riggin.

That being said, the captains and crew definitely encourage you to get involved along the way if you want to and feel comfortable doing so. I really enjoyed getting to help raise the sails one afternoon and even helped bring in the anchor another day. And let me tell you, both were a workout! It was such a fun way to feel like I was actually participating in the sailing experience rather than simply being along for the ride.

Of course, participation is completely optional. The only thing you are expected to do on this trip is sit back, relax, and enjoy the experience!

What to Pack for a Maine Windjammer Trip

Figuring out what to pack for a unique experience like this can be one of the most challenging parts of planning your trip. Of course, what you bring will largely depend on the time of year you’re sailing, but if there’s one piece of advice that applies no matter when you go. Bring layers!

Even during the summer, you never know when the winds on the water might pick up, and it’s always nice to have an extra layer or two with you—especially once the sun goes down and things start to cool off. If you’re sailing during the summer, we were told that some guests even like to go swimming, so definitely pack a bathing suit!

If you’re visiting during the fall as I did, you can probably leave the bathing suit at home and make room for some additional layers instead. Long pants, sweaters, and a windbreaker are all great things to have with you. That being said, Maine weather can surprise you! We had one absolutely perfect day with blue skies, no clouds, and sunshine so warm that I was sailing in a tank top. Having options is key!

When it comes to everything else, keep it simple and pack light. As I mentioned earlier, the cabins are small, and there isn’t much room for storage, so this is not the trip to overpack. Keep toiletries to the essentials, as there isn’t much bathroom space for spreading out your things either. As a woman, I personally wouldn’t even bother bringing makeup or hair tools. Embrace the windblown, living-on-a-sailboat look for a few days!

Finally, bring comfortable shoes with good traction. Non-slip sneakers are especially helpful when moving around the schooner and getting on and off the smaller boat for excursions.

How Much Does It Cost + What’s Included?

The cost of sailing aboard the J. & E. Riggin varies depending on which trip you choose and how many days you’ll be aboard. Rather than listing specific prices here that may change over time, I recommend checking their current sailing schedule for the most up-to-date trip dates and pricing.

One thing to keep in mind when looking at the cost is just how much is included. Your trip price covers your accommodations aboard the schooner, all of your meals throughout the trip, and any excursions you take along the way. Once you’re aboard, so much of the experience is already taken care of for you.

Considering that you’re not only paying for a place to sleep, but also your meals, sailing experience, and adventures along the Maine coast, it really is an incredibly unique way to experience this part of the country.

Enjoy Your Time Aboard the J. & E. Riggin!

I hope this post helped answer some of the questions you may have had about what it’s truly like to live and sail aboard the J. & E. Riggin. And if this is an experience you’ve ever considered doing yourself, I hope I’ve convinced you to take the leap and add it to your bucket list!

Maine is already such a magical place, but getting to experience its beautiful coastline from the water adds an entirely different element to the adventure. From waking up to sunrises on the water and spending your days sailing to the incredible food and unique stops along the way, this is an experience I know I’ll remember for a very long time.

Please feel free to leave any questions or comments below, and as always, happy travels!

FAQ’S

Do you need sailing experience to sail aboard the J&E Riggin?

No prior sailing knowledge is required. Guests can get involved with tasks like raising the sails if they want to, but participation is entirely optional.

What is the J&E Riggin sailing season?

The season runs from late May through early October, with roughly six sails per month.

How many guests can the J&E Riggin accommodate?

The schooner has 11 cabins and can carry up to 24 guests.

What should you pack for a Maine windjammer cruise?

Pack light and bring layers, since cabin storage is limited and Maine weather can shift quickly. A bathing suit for summer sailings, warmer layers for fall, and comfortable non-slip shoes are recommended.

Is there Wi-Fi or cell service aboard?

Cell service is available more often than expected, but it isn’t reliable throughout the trip, and there’s no dependable Wi-Fi.

How long are the sailing trips?

Trips range from 3 to 6 days and nights, depending on the sailing chosen.

What is a Maine windjammer?

A windjammer is a traditional multi-day sailing vessel, often a historic ship repurposed for tourism. The J&E Riggin is a nearly 100-year-old two-masted schooner and a National Historic Landmark.

How much does it cost to sail aboard the J&E Riggin, and what’s included?

Cost varies by trip length and season, but the price covers accommodations aboard the schooner, all meals throughout the trip, and any excursions along the way.