What to Pack for Summer Sailing on Your Maine Windjammer Cruise

what to pack for sailing in Maine on a windjammer cruise

You’ve booked that trip of a lifetime, a sailing vacation in Maine, and now it’s time to get ready. But what will you need? How much should you pack? How much is too much? All great questions, and we’re here to help.

We recently sailed on a Maine windjammer cruise aboard the schooner J. & E. Riggin out of Rockland, Maine, and like most people on their first sailing cruise, we had no idea what to expect. We’d gone camping in Maine for many years and were used to traveling and packing light, so whittling down what to pack seemed like a no-brainer. But sailing on a boat with twenty other cruisers and with limited personal space is altogether different. It’s easy when you’re camping to stow those extra things that you think you might need in the back of a truck or SUV. If something gets left behind at home or an unforeseen need arises, you can get what you need at the camp store or in town. No such luck on a sailing ship at sea. You have to pack only what you’ll need and pack smart.

What to Pack for a Maine Windjammer Cruise

Whether you’re sailing on a windjammer schooner or a smaller ship, sailing isn’t the same as camping on dry land, even on the sunniest of days in Maine. It’s much, much cooler. Plus sailing in the wind and rain can be extremely cold and uncomfortable. So how do you pack for sailing in Maine on a windjammer cruise? This is where we can help! Much of this comes from our camping experience and was easily adapted to several days onboard a historic schooner. You don’t need a lot of fancy sailing gear. Here’s a list of not only what to pack, but things that we know will work.

Let’s start at the top and go head to toe!

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1. A Good UPF-Rated Hat with Lanyard or Bandana

what kind of hat do you pack for sailing in Maine

Many folks on sailing trips prefer ball caps and they can great for keeping your hair looking good in the wind. But while these are okay for coverage, most ball caps don’t offer much in the way of UPF coverage to block the sun’s damaging rays. We recommend a UPF-rated cap or dedicated sunhat for both men and women that has a high UPF rating, usually 50+, and a wider brim to help shield your ears and neck from the rays.

Any hat should also have a way to secure it under your chin so your hat doesn’t go flying off. One girl lost her cute Panama-style hat to the wind and there was no turning back. There are various bandanas with UPF ratings used by fishermen that are very good but will leave your face, neck, and ears exposed.

Lori ordered a great packable Furtalk hat last year for Europe and loves it, and it was perfect for this cruise. Angelo has worn Outdoor Research hats for years and swears by them. Here are some that will keep you feeling — and looking — good!


2. Polarized Sunglasses

My recent pair of Blenders and me on the beach in Florida

My recent pair of Blenders and me on the beach in Florida

Whenever you’re on the water, sunglasses are a must to protect your eyes. But if they’re not polarized, you’re kind of missing the point.

Polarized lenses filter the glare coming off the water so your eyes don’t strain — an important feature to have when you’re sailing. If you don’t want to risk losing a good pair overboard, we don’t blame you for not wanting to spend $300 for a pair of Oakleys or Maui Jims.

But have you heard of Blenders Eyewear? We found this awesome company in California and have 3 pairs to date. They have very cool styles with polarized lenses and the best part? — most are under $50!

>>> Ready to check out a pair of Blenders? Please use our Referral link!

3. A Versatile Travel Scarf to Warm Your Neck

Sailing vacations can be a little chilly as you continually run in and out of the direct sun. Some folks are more sensitive to the sun than others. Combine that with the wind and salt air and exposed skin can quickly become irritated. If you’re prone to sun and wind burn, a light silk or synthetic scarf to wrap around your neck is a good idea. And it can serve double duty to wrap around you if it gets chilly on deck.

4. Shirts and Tops to Layer!

This is where you start to THINK LAYERS! You can check what the forecasted weather is going to be for the duration of your cruise, but just to be safe and comfortable we recommend a long sleeve sun shirt and 2 or 3 tee shirts (the wicking ones are great in any weather). Ladies often like strapped sun tops but we think you’ll find that the sun and the cool (cold!) wind make them impractical. Remember, the water temperature here hovers on one side or the other of 60° F throughout the summer making the air blowing over the deck quite chilly. Short sleeve tops or light pullovers are fine as long as you’re prepared to layer. A great layering choice for over a tee shirt is a single thermal or lightweight fleece pullover. They’re easy to pack and effective. Silk long johns are also excellent for layering and Lori found them to be a great choice for sleeping at night (nighttime temps in early June were below 50 degrees). They’re warm and ultra lightweight under the wool blankets on the ship (windjammer cabins are generally not heated). They are light, can be worn underneath just about anything, dry quickly, and they pack well.

5. It’s All About the Wind — Bring a Good Windbreaker or Wind shirt!

This may very well be your most worn piece of clothing while on board. Be sure to have a really good windbreaker with an adjustable hood. Some can double as a rain jacket making them a good choice for packing and for your budget. Another option is a pullover wind shirt. Golfers seem to like these because they’re slimmer cut than a windbreaker and don’t have a hood. We’ve tried one and it was very good even for layering. Either of these will work so it comes down to personal choice. Just be sure that whichever you choose will fit over a warm layer or two.

6. Sweaters and Sweatshirts to Keep You Toasty

You can certainly layer with a sweatshirt but sweatshirts tend to either be cotton or a synthetic blend making them less effective at keeping you warm especially if they become damp or wet. We recommend that you pack a good wool sweater. Wool will still keep you warm even if it gets damp and nothing is warmer for layering. It need not be a really heavy or bulky sweater. Remember, this is for layering and you’re packing light.

7. Pants and Shorts, Because… well, You need Pants and Shorts

This one’s pretty easy. Wear one and pack the other. Honestly — even on a 7-day cruise, 2 pairs is actually fine! Jeans or hiking pants are both good choices, and bring along a pair of shorts, maybe two in the summer. Hiking pants tend to be lighter than jeans, dry quickly and usually will pack smaller allowing for an extra pair if you like. A pair of light sweatpants can also be nice for lounging on deck at night or in your cabin.

8. Footwear and Socks — Keep Your Sea Dogs Happy!

Tennis shoes, running shoes, sneakers, topsiders — anything with soft soles that offer good traction on deck without marring the deck surface are good options for a windjammer cruise. Lori absolutely loves her Blundstone boots so that’s what she wore. They were the only shoes she wore last year for Europe and they really fit the bill. She wears them for hiking, walking around, and even dresses them up with skirts or a dress. In fact, two of the three crew members on our Maine windjammer cruise were wearing them. Certainly a ringing endorsement! They’re super comfy, durable, great for onshore excursions, and if that’s not enough, they’re also waterproof. Perfect for a rustic cruise. Angelo likes his low cut hikers with a gore-tex lining to keep his feet dry and they don’t have a heavy lug sole. Socks are a personal preference. Wear what best keeps your feet warm and comfy inside your footwear. In June and September wool socks are great but not everyone likes wool socks. We prefer wool/synthetic blends that come in different weights

9. Outerwear: Layers, Layers, Layers

If we can stress one thing for packing for sailing in Maine, it’s to bring light layers. How you tolerate cold or hot will decide what your top layer will be, but one thing is certain, you don’t need a heavy winter parka. Or tons of thick wool layers. Don’t be like Joey Tribbiani! If you’ve planned your layering along with the time of year (more layers for June and September) then your top layer can be as simple as a medium weight jacket, maybe even with light insulation. Peeling off layers is as easy as putting them on and you want something that is roomy enough to fit over everything underneath or maybe warm enough to allow minimal layering in certain conditions. A good jacket will be water resistant, good at blocking the wind, and have a collar that can be turned up to shield your neck. We like fleece lined soft shells. They’re light, warm, pack easily and are great for layering.

Don’t be like Joey!

Don’t be like Joey!

10. Rain Gear, Just in Case

Hopefully you’ll only have sunshine on your cruise but this is Maine and the weather can quickly turn a bit nasty. Because of that we absolutely recommend a rain jacket with a hood and rain pants. You may think that you only need a jacket for a light drizzle or mist, but trust us, a couple hours of wet on deck in the wind and you’re going to have a wet bottom. If you sit, water will run along your seat, and yup, wet bottom. That’s why you need rain pants. They don’t have to match the top. They just have to keep you dry. There are a lot of great lightweight packable rain jackets and pants. Some even fold into a pocket on the jacket making them super packable. Get the jacket and pants separately or get them together, but get them!

NOTE: We don’t recommend rain ponchos for anything least of all on a sailing vessel. They suck in the wind, and on board could get caught or tangled in something making them a danger to you and others.

11. Swim Suit (But Forget the Instagrammable Floatie!)

You might think that we’ve lost it suggesting that you jump into 50° F water, but some people do it. If you’re auditioning for the Polar Bear Club, have at it — bring along a swim suit and a large oversized towel (the ones provided on board are usually the size of a small bath towel). Toward later summer the water usually warms to a brisk but swimmable 55-60° F. But leave the Instagrammable floatie at home. Trust us, it’s just not a good fit!


12. A Dry Bag, Good for Land and Sea

So what are you going to pack all this stuff in to keep it compact and most of all, dry. Remember that there isn’t really room to store luggage in your cabin. Most cruise operators prefer that you pack in a soft sided suitcase of better yet, a duffel. We recommend a duffel and in this case a waterproof duffel or dry bag. They come in a variety of sizes usually measured in liters like a backpack, are lockable, are easy to stow under a berth, and a good one will be as tough as nails so you need not worry about checking it if you’re flying. If the weather turns wet and your cabin becomes damp, keeping your clothes dry so that they’re warm is essential. These are a good investment for most travels where there’s a chance of rain. We use them and here are the ones we prefer.

13. Assorted Sundries

There are things that you will need that you can either pack or pick-up from the local drugstore when you arrive. We find that it’s often easier to buy small sizes of these when we arrive, and then leave them behind for the next folks. It’s also easier if you’re flying rather than dealing with liquids being taken by our friends at the TSA.


The sun is coming at you from all directions when you’re sailing and you’re going to be exposed to both for most of the day so a good sunscreen with a high SPF rating is an absolute essential. We especially like these for both their performance and pleasant scent.


Nothing will ruin that Down East lobster bake you’ve been drooling over more than blood thirsty mosquitoes and black flies. Depending on your anchorage they can also be a nuisance on board. From years of our camping in Maine, this one really works!

Lip Balm

For the same reason that you need sunscreen, add in wind burn. You don’t want dry cracked lips when it’s time to enjoy a meal or relax with a cold one. We’re never without it and this is our favorite.

Reusable Water Bottle

Being exposed to sun and wind all day will make you parched. The schooners carry an ample supply of drinking water but it is at a premium, so to avoid waste and spills bring your own reusable water bottle. They’re easy to keep close at hand, won’t spill if they tip over, and you’ll have water to drink in your cabin. We love these and always pack them along and avoid single use plastics..

Wet Wipes

If you feel it’s necessary for hygienic reasons then by all means bring along a small pack of these disposable wipes. This is another item you need not pack but can pick-up locally before you set sail.

14. Power Up!! It’s Good to Be Prepared with Your Tech Accessories

Solar Charger

Campsites seldom have electricity to recharge battery packs or mobile phones. The same is true of a century old schooner. But what they do have is what Mother Nature so generously provides, the sun. Solar chargers come in a variety of sizes and price points. There are large fold out models and many that are compact. Charge rates vary with size and price. For packing light and providing a reasonable charge time we like these.

Portable Power Charges

Sometimes referred to as power blocks, these also vary in size, available power reserve and price. They’re great for keeping a mobile phone camera charged and ready to use. We have used many different sizes and found that these give the best balance of power to cost without having to pack too many.


Whether you just put fresh batteries in that headlamp or not, bring along an extra set of batteries. You may be going out for only a few days but a flashlight or headlamp that is dead is one of those things that couldn’t be more useless.

Extra Camera Batteries

Many cameras use proprietary batteries. If you plan to take lots of photos, be sure to bring those extra battery packs along. You don’t want to get to the most memorable moment of the trip only to have a camera without power.

15. Other Essentials — Things You’ll Wish You Hadn’t Forgotten

Flashlight or Headlamp

The deck of our windjammer cruise was lighted at night with beautiful kerosene lamps and your cabin will have a small LED lamp over each berth (so generally, 2 lights per cabin). If you want to visit the head (toilet) during the night or spend some time reading in your bunk, you’ll appreciate the better light from a flashlight or a headlamp. We prefer these headlamps for reading and writing whether in a sleeping bag or a bunk. They can always double as a handheld flashlight and are small and easy to pack.

Deck Seats

Some of our fellow passengers brought along these really cool lightweight, padded deck seats, the kind you’d use at a stadium game. If you like having a back to your seat while you read, these are a great idea.


Sometimes that scenic coastline or lighthouse is waaaay over there. Or what kind of seabird was that? Much of your time is going to be spent staring out across the water. An inexpensive compact pair of binoculars make will make this trip so much more enjoyable. If you already have a pair, don’t forget to pack them. If not, check these out.

Ear Plugs

You just met the folks in the cabin next to yours. They seem really nice. But what’s that noise while you’re trying to sleep? Oh no, a snorer! Try not to get annoyed or obsess about the coming night. Enjoy your time on board to the max by packing ear plugs. They’re inexpensive and they work. And the disposable kind fit easily in with your toiletries.

So there you have it — you should be packed and ready in no time at all! You might already own most everything you need to go sailing in Maine whether it’s on a windjammer cruise or a day sailor on Penobscot Bay. But there may be an extra item or two to pick up, so go ahead and treat yourself. This cruise may be the trip of a lifetime. Or if you’re like us, you just might get hooked, and you’ll be planning your next cruise as soon as you’re home!

Bon Voyage!

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