Man carrying a soft-sided bag to a sailboat

Soft-Sided Travel Bags for Sailors

By: Equipment, Product Review, Sailing Tips

I recently spent a long time looking at travel bags. I may have been a bit creepy as I went through Ohare Airport, checking out everybody's luggage. As the airline industry has changed, so has how we travel with luggage. Due to baggage fees, everybody has a carry-on. These convenient, easy-to-roll bags that fit in the above-head compartment have changed. They are bigger, have more features, and frankly, require herculean strength to jam them into those overhead bins. With that comes the screaming from passengers that "their bag" fit on the last flight when being asked to check their overstuffed luggage or the travelers that seemingly cannot understand why there is no room for their carry-on.

These are issues that all travelers face. However, sailors face a different set of issues. A sailboat only has so much space, and when you decide to spend a week on a sailboat vacation, you have some needs that require a bit more luggage.

My instructions are always the same to any of the passengers that join us on American Sailing Vacations, "Pack a small soft-sided bag as there is limited space in a sailboat cabin."

My wife thinks I am crazy and rarely listens to me. So instead, she jams everything into two more giant bags, and then we compromise over space in her bags versus the stuff I must give up for her to fit more shoes in my carry-on.

Why Travel With a Soft-sided Bag

  • If the bag is on your back, there is less chance that they ask you to check it. Soft bags can be forced into tight spaces.
  • On a boat, the soft bags can be stored almost anywhere or stuffed with clothing to act as a pillow. Travel with a cheap, soft pillow case and wrap your bag with it. Presto! You have a pillow.
  • Plenty of soft-sided bags are also waterproof. That means your trip to shore on a dinghy will be a dry one for your belongings. Be careful, though; not all of them float.

Gill Marine Voyager Back Pack

This proper backpack can double as a dry bag and carry-on luggage. While it is 30L, it can be stuffed with so much more. So when it is on your back, it will not get tagged as too big. The front pocket is the right size for travel documents. Inside there is a small pouch for a laptop and a zippered pocket for small storage. Each side has a spot for a thin water bottle. It is a no-nonsense bag that is watertight and durable. 

I easily have carried a week's worth of clothing and two pairs of shoes in this bag. It fits in the overhead compartment of an airplane. On a boat, empty the contents, and this bag folds flat. However, you will continue to use it because it doubles as a daypack, and it can transport your provisions on a soggy dinghy ride.

This is a sailor's dream bag.

Samsonite - EcoDiver Duffel

This bag looks good, feels good, is water resistant, and can hold a lot of clothing. In addition, the 30L version can be stretched tight with gear.

Full disclosure. We bought this soft-sided bag in Italy after we had too much to drink and purchased an entire set of hand-painted dishes. Even though we did not research this bag before we bought it, it is among our best travel bags. The bag performs well and is a regularly used carry-on for our travels. It sits comfortably on your shoulders as a backpack but can quickly transform into a stylish duffel. The 30L version easily conforms to airline carry-on limits.  

The bag is constructed of recycled water bottles. Recyclex™ Material Technology is Samsonite’s range of fabrics and shells created using post-consumer or post-industrial recycled materials that are specially crafted to be durable, flexible and more environmentally responsible.

Patagonia Black Hole Duffel

The Black Hole duffels are bags we have relied on for years for more extensive trips. When our boys went off on sailing expeditions as part of their summer education programs, we could stuff so many snacks in these bags that we were sure they would not go hungry. The ideal size is the 55L backpack duffel. This bag can carry so much more than a typical rolling carry-on bag, and once again, if it is on your back, the airlines seem to not look directly at you but instead down at those pesky people trying to smuggle on oversized rolling bags. 

These bags are durable, waterproof, made from recyclable material, and built for travel. My ideal combo carry-on is the  55L on my back and either the 32L or the 25L as a personal item bag. These bags come in 70L and 100L for those boat trips where you have to check a bag but still need soft-sided luggage.

Osprey Backpacks

My wife swears by her Osprey Farpoint Travel Daypack. When we travel, this pack becomes her purse and personal carry-on item. I have used this pack as a pillow on plenty of sailboat excursions. My boys used their Osprey Momentum 32 as travel bags and school backpacks in high school and college.

These bags have rain guards, multiple pockets, and comfortable straps and are so well made that they last a lifetime. One of my boys has traveled with the bag consistently for 7 years. Trains, planes, monohulls, catamarans, dive boats, and high school hallways and the bags have survived.

Earth Pak

This pack is versatile and is for the sailor that wants to travel as lightly as possible. There are no external pockets on this particular dry bag, and it does not allow you to compartmentalize anything inside. In other words, it is a basic bag that carries all your stuff and keeps it dry. Simple, yet extremely practical for a traveler who just needs their stuff to go along for the ride.

This daypack, drybag, and carry-on backpack has traveled to numerous locations with my family and is often stuffed in another bag as an emergency addition. In addition, it has been used as a grocery bag, primary luggage, and receptacle for gathering water. 

Last Tip

When choosing a bag, you must meet your needs and the requirements both of the carry-on restrictions and the vessel you will be boarding. If these bags seem small, consider packing cubes to help minimize the space your clothing occupies.

Are you ready to start packing?