I should probably start this story by admitting something: when I booked a four-night sailing trip aboard the J. & E. Riggin, a historic schooner off the coast of Maine, I pictured the experience being just a tad more luxurious than it actually was. Not luxury-luxury obviously! I knew I was booking a schooner, not a cruise ship. But in my head there was perhaps a little more…space. Then I saw our cabin.

My dear friend Laurie is one of those people who will pretty much say yes to any adventure I throw her way. The two of us have tackled some interesting experiences together over the years, which is probably why neither of us questioned this particular decision nearly enough before making it.

We arrived at the dock in Rockland, Maine excited, curious and ready for our adventure. Then I started handing our duffel bags down to Laurie as she climbed into our cabin, and I saw it. The sheer look of panic.

Oh. Our cabin was tiny. Like, really tiny.

Two bunks. Enough room for one person to stand at a time. A little reading light, which felt wildly optimistic. Like, Here you go. Enjoy a novel while your roommate is eleven inches from your face. This was essentially a closet with beds.

Let me put it this way: if your idea of a vacation requires a king-size bed, a rainfall shower and a little turn-down service, schooner life may not be for you. Our cabin had approximately enough room for two people, two beds and one very questionable life decision.

Laurie looked at me. I looked at Laurie.

And this is where it’s important to understand the dynamic between the two of us.

We are not one of those friendship duos where one person panics and the other calmly says, everything is going to be fine. Nope. One of us panics, the other joins in, and we feed off each other until we have created a completely unreasonable level of anxiety.

Then we laugh about how insane we both are.

What have we done?

After settling in—or at least putting our belongings somewhere—we gathered on deck with the 20-something strangers who would be sharing this very small floating world with us for the next four days.

We looked around. This was an eclectic group. There were couples, families, people traveling alone and people ranging in age from their 20s all the way to 80. Laurie and I were among the younger passengers, and initially we weren’t quite sure how this was all going to work.

Then came Captain’s Call, where Captain Justin explained how life aboard the schooner would operate. Afterward, we were given the opportunity to head into Rockland for dinner.

Laurie and I practically sprinted off the boat.

I distinctly remember both of us having some version of the conversation:

What have we done? Do you think we can do this for four days? I mean…technically we could still leave.

I’m convinced they keep you tied to the dock the first night specifically for people like Laurie and me who are approximately six minutes away from abandoning ship.

Thankfully, we stayed.

At 6 a.m. the next morning, coffee appeared. And things immediately began looking up.

Life at Sea

We had stopped at Walmart before boarding to buy sleeping pads because we’d suspected there was a decent chance we wouldn’t be sleeping in our cabin. Best purchase of the trip. Laurie and I slept on deck every single night.

And something I initially thought we’d be doing simply because we couldn’t handle our tiny cabin, ended up becoming one of my favorite parts of the entire experience.

At night, we’d crawl under our Rumpl blankets, get cozy and fall asleep to the sounds of the night. One of the nights was so foggy you couldn’t see anything in the bay, but at one point I woke up and was treated to the most amazing, bright orange sliver of a moon over the water. I thought I was dreaming, it was that incredible.

In the morning, we would wake to the sound of the crew getting started for the day and watch the sun come up over the water.

No room service. No king-size bed. No blackout curtains. And somehow, I wouldn’t have traded it.

That was the first of many things I had completely wrong about this trip.

I also went into it thinking we’d spend more time getting off the schooner and exploring little coastal Maine towns. In my head, the boat was almost transportation between destinations.

Instead, we spent probably 90% of our time aboard. I gave in to the fact that the boat itself was the destination and I was totally okay with that. There was nowhere we needed to be. No itinerary packed with sightseeing. No getting dressed for dinner and rushing out the door.

People read. People napped. We listened to music. We talked a lot. We sailed and we swam.

Passengers could help raise and lower the sails, haul the anchor and learn how the schooner operated. Some people enthusiastically jumped in. Laurie and I enthusiastically watched them and told them what a good job they were doing. Participation is completely optional, and I chose the option that involved holding my coffee and offering moral support.

We settled into a rhythm. Coffee at six. Meals together. Music, books, conversation, sailing. Sharing the deck at night with Grandpa Denny. He also couldn’t sleep in the cabin so we created our little nightly routine, the three of us. People started becoming familiar.

Can We Talk About the Food?

I need to make something very clear here because “historic schooner sailing trip” might conjure images of sandwiches, crackers and somebody opening a can of beans for dinner. Absolutely not.

Chef Jocelyn and sous chef Charlie were turning out these beautiful meals from the galley every single day.

Fresh fruit. Gorgeous breakfasts. Freshly baked breads. Salads. Seafood. Platters filled with toppings and sides. Desserts. Food that looked like it belonged at a lovely little restaurant—not on a nearly 100-year-old schooner floating somewhere off the coast of Maine. We ate outside on deck with the water and islands around us. Our only job after finishing these glorious meals was to wash our own dishes. Fine by me!

The food was genuinely one of the biggest surprises of the trip.

And Jocelyn, Charlie and the rest of the crew—Rosie, Marina, Cindy and Captain Justin—were a huge part of the experience.

The Strangers Weren’t Strangers Anymore

I wish I could tell you there was one particular moment when the group shifted, but there wasn’t. It happened gradually. On that first day, Laurie and I were guarded. We weren’t sure what we’d possibly have in common with some of the people around us. Everyone had come from somewhere different. We were different ages. We had different backgrounds and completely different lives waiting for us back home.

But by the second morning, people started emerging from their cabins or in our case, from our blankets on deck and heading for that 6 a.m. coffee.

“Good morning.”

“How’d you sleep?”

Someone would sit down next to you. A conversation would start. And you began learning people’s stories.

One woman had spent her career as a flight attendant. One couple had retired after careers in finance. Another couple was more than a month into a road trip from Texas up the East Coast and didn’t really know where they were headed next. There was a mother traveling with her daughter after losing her husband, who had originally been meant to take the trip with her.

Uncle Tony. Grandma Sally. Molly (love you girl), Grandpa Denny, The Judge..

There were running jokes about a wedding next year and all of us coming back for it.

None of this would make any sense to anyone who wasn’t there. Which is sort of the point.

There was also an onboard merchandise “store,” which I convinced Captain Justin to open during one rainy afternoon and then immediately appointed myself unofficial security, informing everyone they could NOT SHOP YET because THE STORE WASN’T OPEN. By this point, even Justin, who had understandably been a little more businesslike when we first boarded, was laughing along with us. I may have ended up with the biggest merch bill on the whole schooner.

A Lobster Bake on an Island

One evening, we anchored near a small island and headed ashore for a Maine lobster bake. The entire crew jumped in to haul, prep, cook and somehow turn a tiny island into our dinner spot for the night. There was fresh lobster, baked potatoes, corn, etc., plenty of laughs and that kind of easy conversation that happens when a group of people has spent a few days living on a boat together.

Sitting there with the water around us, eating lobster cooked right on the island as the evening settled in, was one of those moments that felt almost ridiculously Maine.

Nothing fancy. Nothing staged. Just really, really good.

A Brief Word About the Heads

Now, before this starts sounding a little too dreamy, we need to discuss the bathrooms.

Or, in sailing terminology, the heads. There were two. For more than 20 people. For four days.

The crew cleaned them three times a day, and they never actually felt dirty but… there comes a point when you’ve been sharing two tiny marine bathrooms with that many human beings when you think: I simply cannot smell this smell anymore.

I used more hand sanitizer during those four days than I think I did during the entirety of Covid.

And when we finally got off the schooner during a stop on Deer Isle, nearly every woman aboard made a beeline for the public restroom. I will protect the details and dignity of those involved, but suffice it to say Laurie and I reached an entirely new level of friendship while sitting in neighboring bathroom stalls laughing hysterically. Schooner life bonds people in unexpected ways.

You might notice I don’t have any pictures to attach to this paragraph. That is on purpose!!!

One Last Day

Our last full day couldn’t have felt more different from the day we’d arrived. It was beautiful and sunny, with that crisp Maine air that makes you want a sweatshirt even when the sun is shining. I sat on deck with a blanket over my legs and finished my book. We drank mimosas in the morning. We sailed for most of the day.

There was nowhere I needed to be.

Later, we anchored near Owls Head, not far from Rockland. That evening, the sky put on one of those beautiful Maine sunsets, and I jumped into the water for one last swim.

Part of me was ready to get off that boat. I wanted a shower. I wanted my own bathroom. I wanted a bed.

But another part of me was already sad that it was ending.

Laurie and I have actually talked about doing another sailing next year.

Which is absolutely insane when you consider that approximately four days earlier we had been wandering around Rockland discussing whether we should flee. But we also keep saying the same thing: What if we could never recreate it? We could sail the same schooner. We could sleep beneath the same stars. We could swim in the same cold Maine water and wake up to coffee at six. But we couldn’t recreate those exact people.

And I think that’s what made this trip what it was. Maybe that’s what surprised me most.

I expected Maine. I expected sailing. I expected beautiful scenery. I didn’t expect the people.

I didn’t expect how quickly strangers could become familiar when you stripped away all the usual distractions. We laughed—a lot. We learned pieces of one another’s lives.

And somewhere in those four days, this completely random collection of people became our people.

Maybe we’re not supposed to recreate it. Some experiences aren’t special because you can repeat them. They’re special because, for a tiny little stretch of time, everything and everyone came together exactly the way it was supposed to.

And maybe that’s what travel is really supposed to do every once in a while. Not just show you somewhere new, but shake you out of what is comfortable and familiar long enough to remind you how quickly strangers can stop feeling like strangers.

Even if it all started with two women standing on a dock in Rockland thinking: What the hell have we done?

What I’d Pack If I Did It Again

If you’re thinking about embarking on your own Maine schooner adventure, this is one trip where what you pack matters. Space is limited, temperatures change quickly, and you are living on a boat, not checking into a hotel with a closet and lots of amenities.

● A small, soft-sided duffel. Seriously. Leave the hard-sided suitcase at home. Future you will be grateful when you’re trying to wedge your belongings into a cabin approximately the size of a pantry.

● A sleeping pad. Even if you fully intend to sleep in your cabin. Our last-minute Walmart purchase ended up being the MVP of the entire trip.

● A warm sleeping bag or blanket if you’re considering sleeping on deck.

● Layers, layers, layers. T-shirts, long sleeves, a sweatshirt or fleece and something warm for mornings and evenings.

● A good rain jacket. This is Maine. On a boat.

● Comfortable shoes with good traction. Maybe some flip flops for the shower?

● A swimsuit. Yes, the water is cold. Do it anyway.

● Warm socks. You’ll thank me at 6 a.m.

● A hat and sunglasses.

● Sunscreen. Being chilly does not mean you aren’t getting sun.

● A headlamp or small flashlight. Especially useful when navigating the boat at night.

● A small battery operated or USB chargeable fan

● A reusable water bottle.

● A book or Kindle. You will actually have time to read it. Imagine that.

● Earplugs and an eye mask, particularly if you’re a light sleeper.

● Toiletries—but pare them WAY down. You do not need your entire bathroom cabinet.

● Hand sanitizer. IYKYK.

● And perhaps most importantly: a sense of humor. Because if you’re going to voluntarily live on a nearly 100-year-old schooner with 20-something strangers, sleep under the stars, share two heads, jump into very cold Maine water and potentially acquire an Uncle Tony along the way, you might as well lean all the way in.

I’ve stayed in beautiful hotels, eaten incredible meals and traveled to places I dreamed about for years. Somehow, some of the trips that stay with me the longest are the ones I never could have planned perfectly. The ones that are a little uncomfortable, a little messy and completely different from what I expected.

I hope reading this inspires you to try something new..maybe even set sail on the J. & E. Riggin Schooner?

If you do, tell them I sent you!

x, Julie

Four Days at Sea, Twenty Strangers and One Tiny Cabin