When I told a friend that I was taking a Maine Windjammer Cruise this summer, she said, “Oh, I can’t wait to see the pictures of you lounging on deck in a flowy caftan that’s blowing in the breeze.” I knew then that she was imagining a sailing trip in the Caribbean or the Greek Islands, and that wasn’t what I should expect from a Maine Windjammer Cruise.
But beyond wearing L.L.Bean versus resort wear, I frankly wasn’t quite sure what was in store for me beyond good food, beautiful scenery, and a unique travel experience. I’ve spent plenty of time driving up and down the Maine coast but experiencing the lighthouses and rocky coastline from the water is a whole different experience, one that I was keen to try.
After spending three days and four nights aboard the Schooner Heritage, I learned first-hand what a Maine Windjammer Cruise is all about. The bottom line is that this type of sailing experience isn’t for everyone, but if you tick certain boxes, a Windjammer Cruise can be a bucket list experience that won’t break the bank.
If you have considered a sailing vacation or thought about a Maine Windjammer Cruise, read on to see if it is the right fit for you.
Note: My trip was hosted by the Maine Windjammer Association and the Schooner Heritage. All opinions are my own.
What is a Windjammer?
If you have never even heard of a Maine Windjammer, let’s start with some background. In the 19th century, coasting schooners were used to transport fruit, fish, lumber, and more between ports along the Eastern Seaboard. These schooners were sailing vessels with two or more masts, often referred to as Windjammers or Windships. Once trucks and trains replaced ships, these schooners nearly became obsolete.
However, Maine artist Frank Swift rescued many of these schooners and capitalized on the growing interest in Maine as a “Vacationland” to offer sailing cruises to adventurous travelers looking to escape the hustle and bustle of urban living. This vision carries forward to today’s Maine Windjammer Cruises, albeit with a few more amenities.
Today, there are nine schooners in the Maine Windjammer Association, the largest fleet of windjammers in the country, five of which have been designated National Historic Landmarks. Each vessel is individually owned, with its own unique story, and each captain adds his or her own character to the experience aboard. With varying weather and crew, no two sailings are exactly the same.
What is Maine Windjammer Cruise?
Maine Windjammers rely on the wind and tide, using nothing but the sails, or sometimes getting a little push from the motorized yawl boat, to navigate the waters of Penobscot Bay, off of Maine’s midcoast. This section of the coast is ideal for sailing holidays, offering a sailing vacation that you won’t find anywhere else in the United States.
Penobscot Bay is dotted with islands, both large and small, that provide both a scenic backdrop and countless coves to anchor at night. Maine Windjammers offer pleasure cruises from three to six nights long, and there are schooners that can accommodate anywhere from 16 to 40 passengers on board, plus a small crew.
While some cruises have themes (e.g. Perseids Meteor Shower, Lobsters & Lighthouses,…) or sail to special events (like the Maine Windjammer Days in Boothbay Harbor), most sailings have no set itinerary. The ships sail wherever the wind, and their captains, take them to find the best weather and best views.
The Maine Windjammer sailing season kicks off in early June and continues through late September. Each ship has different offerings, but the Schooner Heritage that I sailed on offers three, four, and six-night cruises, and the prices range from $780-$1265 per person (for 2022), depending on the length of the cruise and time of the year.
6 Reasons to Book a Maine Windjammer Cruise
As I said before, the Maine Windjammer Cruise isn’t for everyone. You may love cruising, but this is not your typical cruise. A Maine Windjammer cruise may be right for you if you meet the following criteria:
1. You enjoy coastal New England scenery
The Maine Windjammers leave out of Rockland and Camden on Maine’s midcoast. Both of these scenic tourist havens have much to offer visitors, from Rockland’s robust art scene to Camden’s quaint harbor (see my suggestions for things to do in Rockland.) But there is only so much that you can see on the land unless you hop on one of the daily ferries to Vinalhaven or North Haven Islands.
A Maine Windjammer Cruise allows you to see the coast from a whole different perspective. You will sail past numerous lighthouses on your journey, along with rocky coastlines trimmed with pine trees. A Maine Windjammer cruise is also a great way to spot wildlife. Many times throughout my trip I spotted seals, porpoises, ospreys, and other sea birds. The seals and porpoises liked to hang about and spy on us.
2. You Enjoy Meeting Fellow Travelers
If you enjoy group tours and trips and appreciate the opportunity to get to know like-minded individuals, you will appreciate the community aspect of a Maine Windjammer Cruise. This is not a good choice for those seeking alone time.
Maine Windjammer Cruises tend to attract adventurous travelers from across the country. Many are retired professionals, although there may be some families (although this would be better suited for some tweens/teens than young children that need close supervision.)
Every day brings opportunities to interact with and get to know your family travelers. All meals are served family style, lending themselves to conversation. On deck, the guests and crew work together to raise and lower sails or take care of the ship. While sailing or in the quiet evenings, either during “cocktail hour” or after dinner, guests gather in camp chairs on deck and float from one group to the other, making conversation.
Because everyone on board interacts with each other, I think solo travelers will feel just as comfortable as those traveling with a friend, family, or significant other. The community aspect of the experience reminded me a lot of one of our favorite family vacations at the Nine Quarter Circle dude ranch in Montana.
3. You Like to Go with the Flow
If you are someone that doesn’t like their vacation to be too structured and enjoys just going with the flow then you will appreciate a Maine Windjammer vacation. There is not any set itinerary and where you are going can change by the day, or by the hour, depending on the weather. All you know is that you will be sailing.
Likewise, your days are fairly unstructured aboard a Maine Windjammer. The rhythms of the day revolve around two things — meals and sails. You will soon catch on that coffee hour starts around 6:30 am, followed by breakfast at 8:00 am. After that, it is time to raise the sails and catch a breeze to your next destination.
The day may be spent flying with the wind or moving more slowly with the breeze. Lunch will come out when the crew is able and by late afternoon, the captain has found a spot to anchor for the night.
It is then time to lower and fold the sails before breaking open whatever beverage you brought on board for cocktail hour. This is the time when you can go for a swim or take the small row boat out for a view of the Schooner from the water. You may even get a crew member to take you out on the small sailboat that accompanies the Schooner.
Dinner is a sumptuous feast, followed by a homemade dessert. You will be amazed by the quality of food that the crew prepares over a wood-burning stove. After dinner, guests gather to chat, play games, look at the stars, or maybe have a sing-a-long.
Bedtime comes early and guests slowly say their goodnights and make their way below decks to be lulled to sleep by the gentle rocking of the ship.
4. You are an Adventure Traveler
While you may not consider a sailing cruise a form of adventure travel, I think you need to have an adventurous spirit to best enjoy a Windjammer cruise. This is not a luxury cruise with cushy accommodations. In fact, the cabins below the deck are quite small and rustic. On the Schooner Heritage, cabins offer either a single bed, two bunks, or a double bed.
Space is tight, with just enough room to turn around and storage is even tighter. Our cabin had two small shelves, but you don’t often want to leave items on them during the day as they will likely slide off while sailing. There was space to store small duffel or tote bags under the lower bunk. Otherwise, the cabin just consists of a sink with hot and cold water, towel racks, coat hooks, an electrical outlet, and reading lights above the bed.
You may have noticed that I didn’t mention a bathroom. Schooners offer shared bathrooms on the main deck. The Schooner Heritage had three marine heads, one of which also functioned as a private marine shower (basically a kitchen sink hose to rinse yourself). On our ship, two of the cabins actually had private bathrooms. However, those still have a bit of an odor so be careful what you wish for.
I thought of the accommodations as a sort of camping on the water. If you are comfortable tent or cabin camping with a shared bathroom and shower house, you will probably be fine on a Maine Windjammer cruise.
I’ll admit that typically a private bathroom is a must for me, even when glamping. But despite that preference, I still enjoyed the adventure of a Maine Windjammer Cruise. I’d have a tough time on a six-day cruise, to be honest, but the three or four-night was quite doable once the heat wave broke (there isn’t any air conditioning so a small fan is something that I would recommend you pack for a Maine Windjammer Cruise.
5. You Enjoy Guest Participation
Maine Windjammer cruises give you as much opportunity to participate as you desire. It is a great opportunity to learn a little bit about sailing without taking lessons or buying a sailboat. The crew certainly appreciates the help hauling lines and raising sails. They also don’t turn down a bit of help in the kitchen, especially when it comes to cleaning up.
You certainly don’t have to join in. I spent one afternoon sitting in a cozy corner on the deck reading a good book. So if you are feeling a little tired or lazy, don’t feel guilty. There will be plenty of opportunities to join in.
6. LOBSTER!
A highlight of all the Maine Windjammer cruises is a traditional New England lobster bake on the beach. At some point during the cruise, your captain will find a deserted beach and drop anchor. The crew will row the guests and supplies ashore for either a lunch or dinner lobster bake.
It takes some time to build the fire, collect seaweed to cover the lobsters, and cook everything up, giving guests a chance to go for a swim or take a hike along the beach to stretch their sea legs.
Our afternoon on “Lobster Island” (actually Mc Glathery Island) started with chips and dip, followed by hamburgers, hot dogs, and watermelon. Soon those gorgeous soft-shelled lobsters were ready to crack open, along with fresh Maine corn.
I can’t describe the joy of picking apart my fresh lobster on a beach, with nothing but a rock to use as my table. Butter dripping down my face and no one around to notice except my shipmates, who had already seen me bleary-eyed and stumbling to the bathroom in the early mornings.
4 Reasons Not to Take a Maine Windjammer Cruise
If you have read this far and you are still interested in a Maine Windjammer Cruise, then you are probably a good candidate for this type of vacation. However, there are a few other things to keep in mind before you book:
1. You Have Young Children
The audience of the Maine Windjammer Cruises trends a bit older. On my sailing, there was one family with one teen boy and one young adult daughter. However, the rest of the guests were either retirees or in the 50+ age group (my friend being one of the only exceptions.)
That isn’t necessarily a reason for families to stay away. In fact, it could be especially fun to book a Windjammer cruise with a group of friends or as a multi-generational trip. However, I would not want to bring small children on board.
Not only is there not a lot of room to run around without getting underfoot of crew and guests, but parents would need to be constantly vigilant, especially when sailing. When the Schooner heels, the boat can really lean quite a bit and it is easy for loose items (phones, water bottles, etc.) to slip through the small openings on deck. You would want to keep a close grip on young children at that time.
2. You Have Food Allergies
The Captain and crew of the Schooner Heritage did a great job accommodating those guests with certain food sensitivities or dietary restrictions, such as gluten sensitivity, vegetarians, or no seafood. However, if you have a serious food allergy I think it would be challenging to prevent cross-contamination in the small galley.
This is something you would want to talk about with the staff before booking to see exactly what they could accommodate. Just keep in mind that if there is an issue, a hospital is probably 45-minutes or more away by boat.
3. You Have Mobility Issues
There were a couple of passengers on our cruise that had mobility issues and I give them a lot of credit for working through the challenge. However, if you do have mobility issues you should think carefully about whether or not the setup is good for you.
To go below decks to the cabins or galleys, you need to descend a steep staircase, ideally backward for safety purposes. This also means you need to climb up and down these stairs when you need to use the bathroom. For those of us that need to get up and go in the middle of the night, that may not be the safest situation.
While sailing, moving around the deck can be treacherous if you aren’t steady on your feet, especially when the ship is heeling. Even those who are steady on their feet need to hang on when the wind is really blowing. And, decks can get slippery so good boat shoes or supportive shoes with non-skid soles are necessary.
Also, keep in mind that you are either sitting on camp chairs that aren’t super supportive or resting on a deck cushion on the hard deck or galley roof without back support. The cabin mattresses also aren’t exactly Tempur-Pedic, so you will feel all your creaky joints in the morning.
4. You Aren’t a Morning Person
The ship’s crew rises with the sun and immediately gets to work swabbing the decks (yes, that is really a thing) and preparing for the day. The sea birds also like to welcome the morning, even before the sun makes its appearance.
There aren’t many secrets kept on the ship, as sound travels easily and you will hear your fellow shipmates rise and start their days. I highly recommend a good set of earplugs for all passengers, especially light sleepers. I actually won’t travel without my Bose Sleep Buds (this is my affiliate link, if you click and make a purchase I will receive a small commission but even if I didn’t, I’d still sing the praises of the Sleep Buds.) I’d be a wreck without these miracle-working noise-canceling earbuds that also play sleep sounds that mask ambient noise.
Even with earplugs, it is hard to ignore the conversation, laughter, and banging coming from above, along with the sun streaming in. You don’t have to get up early on a Windjammer cruise, but it is pretty hard not to. Plus you want to be ready for the breakfast bell at 8:00 am.
So what do you think…is a Maine Windjammer Cruise for you? Despite the drawbacks, I’m glad I had a chance to experience this unique type of “cruising.” It is much more authentic than those big cruise ships anyway!
My fellow shipmates all had a lovely time too. For some, it was their 10th voyage aboard! Others were returning for their second or fourth sailing, while many of the newbies were strategizing on how to get other couples to join them next year. Even some of the crew had first been passengers in previous years.
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Tamara Gruber is the Founder and Publisher of We3Travel. A former marketing executive and travel advisor, Tamara is an award-winning travel writer and recognized expert in family travel. Tamara is a member of SATW and the Adventure Travel Trade Association, and serves on the Board of the Family Travel Association. She is also the publisher of YourTimetoFly.com and the co-host of the Vacation Mavens travel podcast.
