There are some travel experiences that stop you in your tracks — not because they’re flashy or headline-grabbing, but because they feel like stepping into a completely different rhythm of life. Sailing on the Schooner J. & E. Riggin out of Rockland, Maine was exactly that kind of trip. No Wi-Fi, no rush, no alarm clocks. Just the creak of wood, the snap of canvas sails, and the wild, island-studded waters of Penobscot Bay stretching out in every direction.
In This Guide
I joined the Riggin for the Windjammer Gam — a special sailing voyage featuring live folk music from Brigid & Johnny Reedy — and honestly, I’m still processing how good it was. If you’ve ever wondered what it would be like to sail the Maine coast on a historic wooden schooner, let me walk you through everything.
What is the Schooner J. & E. Riggin?
The J. & E. Riggin is a historic two-masted schooner that has been sailing the waters of Maine since 1927. She’s one of the original Maine windjammers — a fleet of traditional wooden sailing vessels that have been taking passengers out into Penobscot Bay for decades. Today she’s captained by the husband-and-wife team of Captain Justin Schaefer and Captain Jocelyn Schmidt, who run her as a small, family-owned operation with an emphasis on genuine, personal connection.
This is not a cruise ship. There are no casinos, no buffets, no entertainment decks. The Riggin carries a maximum of 24 passengers, which means every trip feels intimate. You get to know your fellow sailors. You help raise the sails if you feel like it. You sit on deck in the evening and watch the sun drop behind the Camden Hills. It’s the kind of travel that puts the world back in its proper scale.
What is the Windjammer Gam?
The word “gam” comes from old whaling tradition — it referred to a social gathering between two ships at sea, a time to swap stories, share food, and make music. The Riggin’s Windjammer Gam keeps that spirit very much alive, and takes it to a whole new level.
The Gam itself happens on the final night of the voyage, when the entire Maine Windjammer fleet converges in one spot. Every schooner in the fleet arrives, drops anchor, and the party begins. Each boat has its own live music playing on deck — on the Riggin, our musicians were Brigid & Johnny Reedy — and guests are free to hop between schooners, exploring each vessel and meeting the passengers and crew from the rest of the fleet.
It’s one of those evenings that’s almost impossible to describe properly. Imagine multiple historic wooden schooners anchored side by side in the dark, each one lit up with lanterns and music drifting across the water between them, while you clamber aboard unfamiliar decks to peek at different boats and swap stories with strangers who’ve just had their own five-day adventure. It was a night to remember.
The Windjammer Gam voyage ran from Thursday evening through to Tuesday morning — five nights at sea.
Getting to Rockland, Maine
Rockland is a working harbour town on the mid-coast of Maine, about two hours north of Portland. The nearest major airports are Portland International Jetport (PWM) — roughly two hours by car — and Bangor International Airport (BGR), about an hour away. Boston Logan (BOS) is also a viable option if you fancy a scenic drive up the coast.
I flew in via Portland, spending a couple of days in Portland (you can see the full guide here) and thenarriving in Rockland the day before boarding so I could spend some time exploring Rockland itself and recording a bit of content around the harbour. I’d strongly recommend this approach — arriving the night before takes the pressure off completely, and Rockland is a genuinely lovely town that deserves more than a quick dash through. I’ve written a full guide to Rockland over on the blog — read it here — but in short, it’s well worth giving yourself extra time there.
The schooner boards at 3 Captain Spear Drive, Rockland, ME 04841, right at the marina. Parking at the marina is available for $20 per vehicle for the duration of your trip.
Arriving on Board: Boarding Night
Boarding opens between 5 and 6 PM on the first evening of your trip. Get there on time — the team holds Captain’s Call at 6 PM sharp, and you really don’t want to miss it. This is a 45-minute introduction from Captain Schaefer covering the layout of the boat, the crew, and a general outline of your upcoming week. It sets the whole tone for the trip and gives you a chance to meet your fellow passengers.
One thing worth knowing: dinner on boarding night is the only meal not served on board. After Captain’s Call, you’re free to head into town for dinner — the boat stays at the dock that first night so you can settle in and find your sea legs before you actually set sail. Breakfast is the first meal served, and you head out onto the water shortly after.
That first evening in town is also a good opportunity to pick up any last-minute bits and pieces you might need for the trip ahead. And while you’re there, I’d highly recommend the crab cakes — I’ve written about where to find them in my Rockland guide, but trust me, do not skip them. It’s a lovely way to settle into your Maine adventure before the sailing begins.
Back on board after dinner, the evening was wonderfully relaxed — nibbles were laid out, and it was the perfect chance to get to know your fellow passengers and settle into your cabin for the night. The social atmosphere on the Riggin starts right from that very first evening.
As for the cabins — they’re cosy and comfortable, typically set up with two single beds. I was lucky enough to have mine to myself, which felt like a real bonus, but it’s worth knowing that cabins are designed to accommodate two people if you’re travelling with a partner or friend.
Life on the Riggin finds its own rhythm surprisingly quickly. You wake up to the smell of breakfast being cooked below, and within a few hours you’re under sail in waters that look like they belong in a painting. Each day brings something different — a new anchorage, a new stretch of coastline, a new reason to stand on deck and stare.
Sailing Activities on the J. & E. Riggin
One of the great joys of the Riggin is how involved you can choose to be. Help raise the sails, haul a line, or take a turn at the helm if you want — the crew will happily have you. Or sit back with a cup of coffee and watch it all unfold. There’s no pressure either way, but I’d encourage you to get stuck in at least once.
Raising the anchor each morning is an experience all of its own. Passengers haul together while Brigid & Johnny play live music on deck — and I cannot overstate how surreal and wonderful that feels. It was like being on the set of a film.
Going Ashore
Each day brought the chance to go ashore somewhere new — you can read about the specific stops in the Where You Sail section below. And on the final morning, a brave group of passengers jumped straight off the side of the boat for a swim in Penobscot Bay. I was very happy cheering them on from the deck.
The Crew and Passengers on Board
Because the Riggin carries a maximum of 24 passengers, there’s a genuinely communal feel. By day two, you’re on first-name terms with everyone on board. I even met a couple who had been returning to the same vessel every single year for around 15 years — when you hear that, you stop wondering whether it’s worth it.
Captain Schaefer and Captain Schmidt run an incredibly warm ship, and that warmth flows through every member of the crew. They take the time to get to know you personally — not in a performative way, but genuinely. And on the final night, watching the crew scale the very tall rigging silhouetted against the sky was a moment that drew everyone on deck to a standstill.
The Food on Board
Let me be very clear about something: the food on the Riggin is extraordinary. Every single day was an absolute foodie heaven, from breakfast through to dinner, and I genuinely did not expect to be as blown away by the galley as I was.
The philosophy is simple and utterly brilliant — if it wasn’t grown in their own garden or pulled straight from the ocean, it was sourced locally. That commitment to provenance shows in every single plate.
Breakfasts alone were a revelation. Freshly made bagels appearing from the galley on a wooden schooner in the middle of Penobscot Bay is not something you forget quickly. Lunches and dinners followed suit — think rich, velvety lobster bisque made with lobster that was practically still swimming an hour before. But the absolute highlight? A fresh lobster bake on a deserted island, with the lobsters cooked over an open fire right on the shore. It is as magical as it sounds.
I should also mention the oysters. I went on this trip as a self-declared oyster hater — and came off it as a complete convert. Freshly shucked, straight from the water, on a wooden schooner in Maine. It turns out the secret to oysters is simply eating them in the right place.
Every meal felt like something a serious chef had carefully considered and lovingly executed — which is all the more impressive when you realise it’s being produced in a tiny galley on a sailing vessel. The Riggin‘s kitchen is, without question, one of the best arguments for booking this trip.
Every meal except the first-night dinner is served on board, including a generous farewell brunch on your final morning. You will absolutely not go hungry — quite the opposite.
Music on the Water: Brigid & Johnny Reedy
Each Windjammer Gam voyage has its own musical guests, and ours were Brigid & Johnny Reedy — a sibling duo from Southwest Montana playing a beautiful mix of Americana, cowboy music, and western folk. And here’s the detail that feels almost too perfect: Johnny has experience crewing historic sailing ships off the coast of Maine. The man was made for this voyage.
Crucially, they sailed with us for the entire trip — not just the final Gam night — and that made all the difference.
Live Music During the Voyage
Having live music woven into every day gave the trip a completely different texture. On the sunny days it was all sun-drenched deck sessions and music drifting across the water. But some of the most memorable moments came on the cold and wet days, when everyone piled into the galley together. Brigid & Johnny would play, the desserts would appear — and they were spectacular — and something about the warmth, the music, and the sound of rain on the deck above made it feel like the cosiest place in the world. Those rainy-day galley sessions are something I’ll be talking about for years.
The Gam Night: Music Across the Fleet
It was on the final night that the music really came into its own. With every schooner in the Maine Windjammer fleet anchored together and a different band playing on each deck, the whole bay became one big floating concert. You’d hop off the Riggin, scramble onto another schooner, and be greeted by a completely different sound, a different crowd, a different boat to explore — then back again. It was chaotic and joyful and unlike anything I’ve experienced in years of travelling.
The combination of live music, historic wooden boats, and the wild darkness of a Maine bay at night is something I genuinely hadn’t anticipated being so moved by.
Want to replicate this exact trip? Brigid & Johnny Reedy are heading back out on the Riggin next year — which means if you book now, you could have the same extraordinary experience I did. Spots on the Windjammer Gam fill up fast, so get in early. Book directly at schoonerriggin.com.
Where You Sail: Penobscot Bay
The Riggin sails the waters of Penobscot Bay — a vast, island-studded expanse of protected water along the mid-coast of Maine. This is some of the most spectacular sailing territory on the East Coast, with granite headlands, spruce-covered islands, lobster boats, and the distant blue silhouette of the Camden Hills.
The route isn’t fixed — it depends on wind, weather, and the captain’s read of conditions — which is part of what makes each voyage unique. You never quite know exactly where you’ll end up, and that sense of adventure is half the joy.
Castine, Maine
Castine is a charming historic town on the eastern shore of Penobscot Bay. There isn’t a huge amount to do there, but honestly that’s part of the appeal. After days at sea, simply stretching your legs on solid ground and strolling past the beautiful historic homes lining the streets felt like exactly the right kind of stop.
Swan’s Island
Swan’s Island is a quiet, beautiful island where we went ashore and toured the lighthouse. There’s something about standing at a Maine lighthouse that makes the world feel very still and very large at the same time.
A Deserted Island Lobster Bake
One of the most magical stops wasn’t on any map we were given in advance — a deserted island where the crew set up a fresh lobster bake over an open fire on the shore. I’ve covered it in full in the food section, because it absolutely deserves its own moment.
Practical Information
Vessel: Schooner J. & E. RigginAddress: 3 Captain Spear Drive, Rockland, ME 04841 Website:schoonerriggin.comPhone: (800) 869-0604 Captains: Justin Schaefer & Jocelyn Schmidt Max passengers: 24 Trip length: 5 nights (Thursday evening to Tuesday morning) Nearest airports: Portland (PWM) ~2 hrs, Bangor (BGR) ~1 hr, Boston (BOS) ~3.5 hrs
Booking: Trips can be booked directly through schoonerriggin.com. As a repeat passenger you receive a 10% discount if you book your next trip before 1st February. They also offer charter voyages.
Cancellation policy: Cancellations more than 8 weeks before boarding are eligible for a refund minus a $150 per person fee. Inside 8 weeks, payments are generally non-refundable. Trip cancellation insurance is strongly recommended.
What to Pack
The Riggin requires a soft duffel bag (no hard-sided luggage — space is limited on board). Beyond that, the key is layering. Maine in June can be glorious sunshine or cool fog, often on the same day.
Must-haves for a Maine windjammer trip:
Waterproof jacket / foul-weather gear (I purchased these off their website and came in very handy.
Warm layers (fleece or wool — it can be cold on the water even in summer)
Soft-soled shoes or deck shoes (no black-soled shoes)
Sunscreen, hat and sunglasses (I got very burnt when I forgot to wear my hat on the last day of sailing)
A good book or two
Leave the stilettos at home. This is gloriously, wonderfully not that kind of holiday.
Is the J. & E. Riggin Worth It?
Absolutely — but with a clear-eyed caveat: this is not for everyone. If you need Wi-Fi, air conditioning, a private bathroom, or a predictable schedule, a windjammer voyage will challenge you. The cabins are cosy (read: small), you share bathrooms, the schedule is at the mercy of the wind, and there’s nowhere to disappear to if you fancy solitude.
But if you’re the kind of traveller who wants to slow right down, disconnect, eat incredibly well, sleep deeply to the sound of water, and find yourself talking to strangers who feel like old friends by day three — the Riggin is genuinely one of the most special things I’ve done in years of travel.
When I got back to shore, the first thing I noticed was that I could still feel the sway of the water — that gentle rocking that stays with you for days after you leave. But beneath that, something else had settled in too: a deep, quiet sense of contentment. The slower pace of life on the Riggin had a way of holding up a mirror to how fast I normally move through the world — and the contrast was impossible to ignore. Five days with no deadlines, no rushing, no noise beyond the wind and the water and the music, and suddenly your whole nervous system recalibrates. I didn’t expect to come home feeling less like I needed a holiday, and more like I’d finally remembered what rest actually feels like.
FAQ
How many people sail on the J. & E. Riggin? A maximum of 24 passengers per voyage, making it a very intimate and personal experience.
Is the J. & E. Riggin suitable for solo travellers? Absolutely. I travelled solo and found the communal nature of the trip made it one of the best ways to meet people I’ve ever experienced. You eat together, sail together, and by the end of five days you genuinely feel like you know your fellow passengers.
What is the accommodation like on board? Cabins on the Riggin are compact but comfortable, typically set up with two single beds. I was lucky enough to have mine to myself, but they’re designed to accommodate two people — perfect if you’re travelling with a partner or a friend. Think snug rather than spacious, but after a day of fresh sea air you’ll sleep like a log regardless.
Do I need sailing experience? Not at all. The crew handles all the sailing, but if you want to help raise the sails or haul a line, they’ll happily show you how — and it’s a lot of fun. You can be as hands-on or hands-off as you like. Just be warned: once you’ve helped raise a sail on a historic wooden schooner in Penobscot Bay, you may never want to go back to a normal holiday.
What is the food like on the J. & E. Riggin? Outstanding — genuinely one of the best parts of the trip. Everything is either grown in their own garden, caught fresh from the ocean, or locally sourced. Highlights include freshly made bagels at breakfast, a rich lobster bisque, and a fresh lobster bake cooked over an open fire on a deserted island. Every meal from breakfast to dinner is a masterpiece. The final morning brunch is especially good.
When is the best time to sail in Maine? The sailing season on the Riggin typically runs from late May through October. June through August offers the warmest weather; early June brings fewer crowds and the distinctive misty, moody Maine light that photographers love.
Is there Wi-Fi on board? Yes, there is Wi-Fi on board — but honestly, once you’re out on the water you won’t want it. The scenery, the company, and the pace of life on a windjammer make it very easy to forget your phone exists.
What should I do with the nights before and after the trip? I’d recommend spending at least one night in Rockland before and after — I have a full guide to the town on the blog, so head over and read my Rockland guide here for everything you need to know. In short: it has a lovely arts scene, great seafood, and the Farnsworth Art Museum is well worth a few hours.
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Disclosure: This trip was hosted by the Schooner J. & E. Riggin. As always, all opinions are my own. This post may contain affiliate links, meaning I may earn a small commission at no extra cost to you if you book through my links.
In 2006, my husband and I made a life-changing decision that would shape the next chapter of our story. With three little ones in tow, we packed up our lives and moved to Taiwan, beginning what would become an incredible 18-year Asian adventure.
