Maine Windjammer Cruise: Glamping on Penobscot Bay

This article may contain referral links. Read our DISCLOSURE

If you’re looking to relax and unplug, a Maine Windjammer Cruise is the answer. My Itchy Travel Feet featured writer, Debi Lander of ByLanderSea, says it’s like “glamping on the sea.” Read about her experience on a 3-day schooner cruise that explores the beautiful Penobscot Bay, courtesy of the Lewis R. French.

My boyfriend, John, and I are not sailors. Neither are we into camping.

As boomers, we enjoy a touch of luxury and occasionally a fine bottle of wine. But, we also enjoy the challenge of an adventure, and I’m known for trying just about anything. So, we signed up for a Maine Windjammer cruise.

What to do before a Maine Windjammer cruise

We would first spend a few days hiking in Acadia National Park, near Bar Harbor, Maine. Top priorities were the summit of Cadillac Mountain, the tallest peak on the east coast, and a hike around Jordan Pond. We also planned to indulge in lobster and wild Maine blueberry pie.

Visit Camden

The Camden harbor is lovely at twilight. Photo by Debi Lander.

Our trip began with a two-night stay in Camden, Maine. For accommodations, we chose the Blackberry Inn, a lovely bed and breakfast within walking distance of the main street. The owners prepared exceptional two-course breakfasts. We enjoyed ours on the outdoor patio. 

In Camden, we browsed the shops and lingered in art galleries, and dined on more fine food. Our dining experience at Natalie’s was exceptional in every way: white table cloth service,  wine pairings, and a chef who formerly worked at the French Laundry. The splurge to dine at Natalie’s is well worth it.

We stopped into the local brew pub, Sea Dog Brewing Company, for a casual drink at the bar overlooking the harbor. John, a man who needs his morning espresso, recommends the coffee shop named Zoot.

View of Camden, Maine, from Mt. Battie. Photo by Debi Lander.

Don’t miss Mt. Battie above Camden. Drive up for a 180-degree panoramic view of Penobscot Bay and harbors. Wow! The overlook is simply stunning and gives you a feel for the immense size of the bay.

Explore Rockland

The long walk to Rockland Breakfront Lighthouse. Photo by Debi Lander.

In nearby Rockland, we strolled out to the Rockland Breakfront Lighthouse, resting almost a mile offshore. The massive granite pathway took 18 years and nearly 800,000 tons of granite to complete.

Rockland’s other highlight sits downtown, the Farnsworth Art Museum, home to hundreds of artworks by Andrew, N.C., and Jamie Wyeth, among others. The Wyeth family summered in the area, and numerous paintings reflect life along the New England coast. 

Boomer Travel Tip

In today’s travel climate, trip insurance is a must. Compare policies and rates at InsureMyTrip.

The Lewis R. French, Our Windjammer Schooner

The Lewis R. French. Photo by Debi Lander.

The Maine Windjammer Association (website) maintains a fantastic fleet of nine schooners that offer 3, 4, or 6-day schooner vacations. These are former merchant ships propelled by sails that sail out of Camden or Rockland starting in late May to mid October.

We planned our Maine trip around a three-night cruise on the Lewis R. French (website), a 65-foot wooden sailboat launched in 1871. The French, the oldest known two-masted schooner in the United States, remains one of the few in active service. Today, she operates much as she would have 150 years ago, with everything done by hand. 

The historic schooner carries 20 passengers in four single cabins, six double bed cabins, and two bunk bed cabins. Each room includes a sink, a window, reading lights, and a USB charger, but no toilet.

The two heads (bathrooms) are on the main deck. While a generator keeps food cold, the French has no engine.  

Boarding the Boat

Captain Becky Wright at the wheel. Photo by Debi Lander.

We boarded in the early evening, then listened as Captain Becky Wright explained the logistics. Afterward, we took our duffel bags below deck to stash in our cabin.

Yikes! It was tiny and cramped, but I kept reminding myself that we were aboard a national historic landmark.

Captain Becky said, “Your cabin will feel bigger each day.” She was right— rather remarkable how we adapted and how the cabin ended up offering much of what made this trip so memorable. 

We slept listening to the waves lapping against the wooden hull.

Day 1 of a Maine Windjammer Cruise

And the Maine Windjammer Cruise begins. Photo by Debi Lander.

By 6:30 am, we were both up on the main deck enjoying a mug of coffee. I grabbed a freshly baked Danish, while we chatted with the other early risers on the schooner. Most of the participants, like ourselves, are not sailors.

At 8 am, the chef served a full breakfast: blueberry pancakes, eggs, fresh fruit, and various homemade breads and jams. Yum. When finished, everyone washes their dishes in the tubs provided, one of the few jobs required of each guest.

We then set out into Penobscot Bay with the aide of a yawl (small boat) motoring us out of the crowded harbor. Once in the clear, the passengers help to hoist the sails, though that’s not a requirement.

Hoisting the sails. Photo by Debi Lander.

As the workers grunted,” Heave-ho,” Captain Becky sang a lively sea shanty. Strong arms worked to unfurl and raise the mainsail. The smaller sails take less umph.  

Slowly, the French began to move, cutting silently through the water as easy as a knife cuts through soft butter. From then on, Mother Nature dictated the journey as there is no set itinerary. It felt somewhat strange to know that we were going nowhere in particular.

The greatest benefit of a windjammer cruise is that it allows participants to sit back and relax, read, sunbathe, or nap.

I loved looking up at the tall masts and billowing sails. Watching them made it easy to imagine stepping back in time and pondering the hardships of a long  Atlantic crossing. Unlike schooner passengers of the past, I had it easy and savored the moment.

Anyone addicted to their smartphone should note: You can charge a smartphone in your cabin, but getting Wi-Fi reception becomes difficult on the bay. Instead, cruisers unplug from cell phones to join the sport of daydreaming, perhaps something we should do more often.

For lunch, the cook served a delicious chowder and hearty salad. I believe he has a sweet tooth, like me — his cookies are hard to resist. Chef works magic preparing the meals and snacks on a wood stove burning in a tiny galley.

Getting ready for the traditional lobster bake. Photo by Debi Lander.

Around 4:30, we anchored near an uninhabited island for a traditional DownEast event on every windjammer cruise — a traditional lobster bake. The cook and assistant paddled a rowboat with all the preparations as we shuttled over via a small motor boat (carried onboard).

While the crew dug a firepit for grilling hot dogs, hamburgers, and vegetable kebobs, the guests took the time to explore the island.

Into a huge pot over another fire lit on the beach went seaweed. When steam started escaping from the lid, we all threw in about 40-some lobsters and corn on the cob (still in their husks).

At dinner time, everyone sat on cushions with toes in the sand and feasted – as much as you wanted. Afterward, we roasted marshmallows for s’mores.

Feeling full from the lobster feast and perhaps tired from the sea air, we fell into bed early. We giggled as we maneuvered into the snug space but now found it welcoming.

Day Two on Penobscot Bay

Curtis Lighthouse. Photo by Debi Lander.

The next morning, we awoke to rain. An awning covering most of the deck kept us dry, and hot coffee warmed our hands.

Chef had freshly baked cinnamon buns waiting. Fortunately, the skies cleared when the crew was ready to set sail.

On this day, I helped by rinsing off the anchor chain while others pulled it from the bottom of the bay. The process requires a few able bodies to manually crank a roller and carefully arrange the chain in a designated space. Every square inch of this old schooner is planned and accounted for, although the lounging spots on deck were ample.

Penobscot Bay offers countless picturesque islands (some an acre or less), a rich contrast to the expansive blue water. Captain Becky steered the sailboat as we sat back, taking in sight a few gorgeous summer homes along the Maine coast plus lots of lobster traps.

Goose Rocks Light. Photo by Debi Lander.

We noticed many historic lighthouses, vital for sailors before GPS, and many still operating today. One squatty little version named Goose Rocks Light appeared, seemingly in the middle of nowhere and surrounded by water.

Late afternoon calls for snacks and drinks. Bring your own beer or wine to be stored in onboard coolers. The chef never lets anyone go hungry. He presented fresh vegetables and dips, one featuring leftover lobster, cheese, and crackers.

Around this time, stronger winds brought the thrill of being under full sail. I loved the spray on my face and the rocking of the boat.

Unfortunately, the wind took us toward an afternoon storm. We anchored and let it blow through, watching another windjammer do the same. A Coast Guard boat checked on the small sailboats scurrying for safety.

The weather becomes a crucial factor on a sailing cruise. We ended up mooring overnight. 

We used the downtime before dinner to crank homemade ice cream, each guest taking a two-minute turn while telling a story, singing a song, or reciting a poem. That and working together produced a bonding among all — crew and guests alike.

You won’t get this on a mega ocean liner. It’s the nothingness on windjammer cruises that is something.

Sunset on Penobscot Bay. Photo by Debi Lander.

That evening we were blessed with a vibrant sunset. When I awakened at night to use the toilet, I gazed upon an incredible starry sky reminiscent of a Van Gogh painting.

Day Three return to Camden Harbor

I felt a bit sad to see the last morning dawn. We enjoyed another homey and hearty breakfast and then began the return to Camden Harbor. It was a beautiful day but with very little wind.

Captain Becky said one of her fears was a sudden big gust, but today she had no worries. We needed to use the yawl boat to promote forward progress to make a timely docking. 

Boomer Travel Tip

We highly recommend joining a medical evacuation program before leaving on an active international trip. Start your Medjet membership here.

Highs and Lows of Maine Windjammer Cruises

Three Maine schooners docked in Camden, Maine. Photo by Debi Lander.

To summarize, a windjammer cruise vacation offers a rustic experience, nothing like a cruise on an ocean liner. Don’t expect a party boat, seated dinners, or four or five-star luxury. I’d call it akin to glamping, with less emphasis on luxury.

The cabins below the deck are tiny, meant for sleeping and not much more. A small sink allows for face washing and teeth brushing. There is no cabin steward.

Showering is a different story. You can take a make-shift shower before breakfast or late afternoon if there is hot water. The space in the head proves difficult at best. Most of us opted for a navy shower — a washcloth over the body.

Cruise along Maine’s coast. Photo by Debi Lander.

Our cruise exploring coastal Maine lasted just three nights. For those on longer voyages, many jump ship into the bay — a cold but accommodating bathing tub.

Penobscot Bay is huge, but windjammers are not sailing on open water in the Atlantic. More than likely, you will not encounter big waves. Those prone to seasickness may want to pack medication or seasick bands, just in case.

The romantic escape brings the wind in your face, the smell of the sea, and the sound of waves lapping against the wooden hull. The chance to escape the everyday world, twiddle your thumbs, or dive into a good book is rare. But those joys are plentiful on a windjammer cruise.

I’d be delighted to sail on one again — I relished the exciting yet relaxing sea journey. I highly recommend it for those who enjoy being outdoors, are willing to use communal toilets, can unplug, and aren’t germaphobic. It’s the kind of trip you’ll tell stories about forever.

A hearty thanks to the Maine Windjammer Association, the Lewis R French, and her fabulous crew.

Scratch those itchy travel feet!

Boomer travelers rely on our weekly email newsletter for fresh travel inspiration, tips, and advice. It's free! No spam, unsubscribe anytime.